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Table numbers are rounded to 7 significant digits; decoded details retain full precision.
Golden et al. 2025 Mantis liquid-handler HTE (OPRD, 10.1021/acs.oprd.5c00216)
Dataset description
960 microscale HTE reactions (ten 96-well plates) from Golden, Roberts, Del Valle et al., 'Enhancing High-Throughput Experimentation Liquid-Handling Capabilities via Strategic Hardware Development of the Mantis Liquid Handler', Org. Process Res. Dev. 2025 (doi:10.1021/acs.oprd.5c00216), transcribed from SI Tables S2, S3 and S7-S14. Several screens with different templates are kept together: (1) S2/S3: ketoreductase screens (96 Prozomix KREDs, catalog codes only) of 6,7-dihydrocyclopenta[b]pyridin-5-one and BMT-238442 (4-(6-fluoroquinolin-4-yl)cyclohexan-1-one), outcome = product/1,3,5-trimethoxybenzene UPLC area ratio; (2) S7/S8: O-alkylation of 4-hydroxybiphenyl with hexyl mesylate, 6 bases x 4 solvents x 2 concentrations x 2 replicates, run with PP-body (S7) and FEP-body (S8) Mantis chips, outcomes = product UPLC area % and product/di-tert-butylbiphenyl ratio; (3) S9/S10: amide coupling of 2-methoxybenzoic acid and 2-chlorobenzylamine, 3 activators x 8 bases x 4 solvents, manual (S9) vs Mantis-integrated (S10) dispensing; (4) S11-S14: Mantis-first amide couplings of acids c1-c4 with 2-(cyclohex-1-en-1-yl)ethan-1-amine, 3 activators x 8 bases x 4 solvents. All outcomes are UPLC internal-standard ratios or area percent, not yields. Tables S1 and S4-S6 (chip types, dispensing calibrations, evaporation) are not reactions and are omitted.
Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.
| Location | Record | Inputs and roles | Temperature | Reported measurements | Source |
|---|---|---|---|---|---|
| reactions[0] | Record 1 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-001 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.61 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[0]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A1"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-001"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-001"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A1",
"row": "A",
"col": "1"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.609999895095825
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[1] | Record 2 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-003 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.69 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[1]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A2"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-003"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-003"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A2",
"row": "A",
"col": "2"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.690000057220459
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[2] | Record 3 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-006 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.63 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[2]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A3"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-006"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-006"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A3",
"row": "A",
"col": "3"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.630000114440918
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[3] | Record 4 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-007 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.56 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[3]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A4"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-007"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-007"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A4",
"row": "A",
"col": "4"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.559999942779541
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[4] | Record 5 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-010 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[4]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A5"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-010"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-010"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A5",
"row": "A",
"col": "5"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[5] | Record 6 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-011 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[5]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A6"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-011"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-011"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A6",
"row": "A",
"col": "6"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[6] | Record 7 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-013 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.64 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[6]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A7"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-013"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-013"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A7",
"row": "A",
"col": "7"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.640000104904175
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[7] | Record 8 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-018 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[7]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A8"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-018"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-018"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A8",
"row": "A",
"col": "8"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[8] | Record 9 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-023 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.55 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[8]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A9"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-023"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-023"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A9",
"row": "A",
"col": "9"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.549999952316284
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[9] | Record 10 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-024 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.68 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[9]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A10"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-024"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-024"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A10",
"row": "A",
"col": "10"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.680000066757202
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[10] | Record 11 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-031 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.69 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[10]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A11"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-031"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-031"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A11",
"row": "A",
"col": "11"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.690000057220459
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[11] | Record 12 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-035 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[11]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well A12"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-035"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-035"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "A12",
"row": "A",
"col": "12"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[12] | Record 13 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-048 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.39 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[12]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B1"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-048"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-048"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B1",
"row": "B",
"col": "1"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.390000104904175
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[13] | Record 14 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-049 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.38 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[13]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B2"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-049"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-049"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B2",
"row": "B",
"col": "2"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.380000114440918
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[14] | Record 15 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-059 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.43 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[14]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B3"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-059"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-059"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B3",
"row": "B",
"col": "3"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.430000066757202
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[15] | Record 16 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-061 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.55 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[15]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B4"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-061"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-061"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B4",
"row": "B",
"col": "4"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.549999952316284
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[16] | Record 17 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-067 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.36 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[16]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B5"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-067"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-067"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B5",
"row": "B",
"col": "5"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.359999895095825
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[17] | Record 18 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-068 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.46 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[17]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B6"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-068"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-068"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B6",
"row": "B",
"col": "6"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.4600000381469727
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[18] | Record 19 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-069 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.48 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[18]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B7"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-069"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-069"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B7",
"row": "B",
"col": "7"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.4800000190734863
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[19] | Record 20 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-075 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.43 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[19]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B8"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-075"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-075"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B8",
"row": "B",
"col": "8"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.430000066757202
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[20] | Record 21 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-076 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.5 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[20]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B9"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-076"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-076"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B9",
"row": "B",
"col": "9"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[21] | Record 22 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-078 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.56 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[21]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B10"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-078"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-078"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B10",
"row": "B",
"col": "10"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.559999942779541
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[22] | Record 23 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-083 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.52 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[22]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B11"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-083"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-083"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B11",
"row": "B",
"col": "11"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5199999809265137
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[23] | Record 24 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-084 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.53 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[23]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well B12"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-084"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-084"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "B12",
"row": "B",
"col": "12"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5299999713897705
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[24] | Record 25 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-098 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.63 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[24]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C1"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-098"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-098"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C1",
"row": "C",
"col": "1"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.630000114440918
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[25] | Record 26 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-103 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.53 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[25]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C2"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-103"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-103"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C2",
"row": "C",
"col": "2"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5299999713897705
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[26] | Record 27 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-105 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.69 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[26]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C3"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-105"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-105"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C3",
"row": "C",
"col": "3"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.690000057220459
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[27] | Record 28 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-109 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.66 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[27]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C4"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-109"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-109"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C4",
"row": "C",
"col": "4"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.6600000858306885
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[28] | Record 29 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-111 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.65 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[28]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C5"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-111"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-111"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C5",
"row": "C",
"col": "5"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.6500000953674316
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[29] | Record 30 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-112 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.53 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[29]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C6"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-112"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-112"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C6",
"row": "C",
"col": "6"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5299999713897705
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[30] | Record 31 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-114 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.68 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[30]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C7"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-114"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-114"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C7",
"row": "C",
"col": "7"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.680000066757202
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[31] | Record 32 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-118 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.56 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[31]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C8"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-118"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-118"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C8",
"row": "C",
"col": "8"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.559999942779541
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[32] | Record 33 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-119 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.67 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[32]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C9"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-119"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-119"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C9",
"row": "C",
"col": "9"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.6700000762939453
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[33] | Record 34 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-120 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.72 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[33]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C10"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-120"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-120"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C10",
"row": "C",
"col": "10"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.7200000286102295
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[34] | Record 35 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-122 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.67 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[34]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C11"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-122"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-122"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C11",
"row": "C",
"col": "11"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.6700000762939453
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[35] | Record 36 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-124 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.62 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[35]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well C12"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-124"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-124"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "C12",
"row": "C",
"col": "12"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.619999885559082
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[36] | Record 37 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-126 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.45 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[36]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D1"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-126"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-126"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D1",
"row": "D",
"col": "1"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.450000047683716
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[37] | Record 38 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-146 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[37]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D2"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-146"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-146"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D2",
"row": "D",
"col": "2"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[38] | Record 39 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-150 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.64 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[38]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D3"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-150"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-150"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D3",
"row": "D",
"col": "3"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.640000104904175
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[39] | Record 40 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-151 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.58 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[39]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D4"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-151"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-151"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D4",
"row": "D",
"col": "4"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5799999237060547
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[40] | Record 41 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-158 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.04 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[40]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D5"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-158"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-158"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D5",
"row": "D",
"col": "5"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.0399999618530273
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[41] | Record 42 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-161 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 3.77 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[41]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D6"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-161"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-161"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D6",
"row": "D",
"col": "6"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 3.7699999809265137
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[42] | Record 43 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-167 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.63 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[42]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D7"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-167"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-167"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D7",
"row": "D",
"col": "7"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.630000114440918
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[43] | Record 44 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-170 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.57 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[43]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D8"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-170"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-170"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D8",
"row": "D",
"col": "8"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.569999933242798
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[44] | Record 45 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-173 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.65 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[44]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D9"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-173"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-173"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D9",
"row": "D",
"col": "9"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.6500000953674316
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[45] | Record 46 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-181 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.62 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[45]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D10"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-181"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-181"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D10",
"row": "D",
"col": "10"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.619999885559082
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[46] | Record 47 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-186 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.71 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[46]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D11"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-186"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-186"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D11",
"row": "D",
"col": "11"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.7100000381469727
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[47] | Record 48 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-187 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.53 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[47]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well D12"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-187"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-187"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "D12",
"row": "D",
"col": "12"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5299999713897705
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[48] | Record 49 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-249 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.47 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[48]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well E1"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-249"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-249"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "E1",
"row": "E",
"col": "1"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.4700000286102295
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||
| reactions[49] | Record 50 | CATALYST: glucose dehydrogenase (GDH) REAGENT: NADP+ REAGENT: disodium hydrogen phosphate REAGENT: sodium dihydrogen phosphate REAGENT: alpha-D-glucose SOLVENT: water CATALYST: PRZ-261 REACTANT: 6,7-dihydrocyclopenta[b]pyridin-5-one SOLVENT: dimethyl sulfoxide | 30 CELSIUS | 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol · CUSTOM: 2.52 [UPLC-MS] | 10.1021/acs.oprd.5c00216 |
Decoded fields · reactions[49]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "SI table and well",
"value": "Table S2, well E2"
}
],
"inputs": {
"GDH": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "glucose dehydrogenase (GDH)"
},
{
"type": "CUSTOM",
"details": "cofactor-recycling enzyme shown in the SI scheme; source and amount not reported (assumed present in the kit)",
"value": "glucose dehydrogenase (GDH)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "not stated in the SI; drawn in the reaction scheme"
}
},
"buffer/cofactor stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "NADP+"
},
{
"type": "SMILES",
"value": "NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]2O[C@H]([C@H](OP(=O)(O)O)[C@@H]2O)n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O"
}
],
"amount": {
"moles": {
"value": 2.0299999713897705,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "disodium hydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].[Na+].OP([O-])([O-])=O"
}
],
"amount": {
"moles": {
"value": 76.11000061035156,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "sodium dihydrogen phosphate"
},
{
"type": "SMILES",
"value": "[Na+].OP(O)([O-])=O"
}
],
"amount": {
"moles": {
"value": 177.58999633789062,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "alpha-D-glucose"
},
{
"type": "SMILES",
"value": "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O"
}
],
"amount": {
"moles": {
"value": 65.12000274658203,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 800 uL per well"
}
},
"ketoreductase (pre-plated)": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "PRZ-261"
},
{
"type": "CUSTOM",
"details": "Prozomix ketoreductase catalog code; pre-plated in the kit well, amount not reported",
"value": "PRZ-261"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1,
"addition_device": {
"type": "NONE",
"details": "pre-plated in the kit"
}
},
"substrate stock": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydrocyclopenta[b]pyridin-5-one"
},
{
"type": "SMILES",
"value": "O=C1CCc2ncccc21"
}
],
"amount": {
"moles": {
"value": 12.149999618530273,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "NAME",
"value": "dimethyl sulfoxide"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2,
"addition_device": {
"type": "CUSTOM",
"details": "Mantis continuous-flow PFE chip, 200 uL per well"
}
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "Prozomix pre-plated ketoreductase kit, 2 mL 96-well plate; sealed with a pre-slit square cap mat",
"material": {
"type": "PLASTIC",
"details": "polypropylene deep-well plate (assumed; pre-plated kit)"
},
"volume": {
"value": 2,
"units": "MILLILITER"
},
"vessel_id": "Table S2 KRED plate (Prozomix pre-plated KRED kit)",
"position": "E2",
"row": "E",
"col": "2"
},
"is_automated": true,
"automation_platform": "Formulatrix Mantis liquid dispenser, continuous-flow PFE chip"
},
"conditions": {
"temperature": {
"control": {
"type": "DRY_ALUMINUM_PLATE",
"details": "Eppendorf ThermoMixer C heating block"
},
"setpoint": {
"value": 30,
"units": "CELSIUS"
}
},
"stirring": {
"type": "CUSTOM",
"details": "orbital shaking, Eppendorf ThermoMixer C",
"rate": {
"rpm": 900
}
}
},
"notes": {
"procedure_details": "Buffer stock: NADP (178.4 mg, 0.24 mmol), Na2HPO4 (1281.3 mg, 9.0 mmol), NaH2PO4 (2521.2 mg, 21.0 mmol) and alpha-D-glucose (1383.6 mg, 7.7 mmol) in water (94.6 mL). Substrate stock: 6,7-dihydrocyclopenta[b]pyridin-5-one (1.3 mmol) in DMSO (21.4 mL). The Mantis added 800 uL of buffer stock and 200 uL of substrate stock to each well of the Prozomix KRED plate. The plate was sealed and shaken (900 rpm) for 18 h at 30 C (scheme: 16-20 h). Workup: 800 uL of 1,3,5-trimethoxybenzene in MeCN (internal standard) was added, the plate was shaken for 15 min, 200 uL was transferred to a collection plate and diluted with 300 uL MeCN:water (4:1) for UPLC-MS. Per-well amounts are the stock amounts scaled by the dispensed volume. The SI gives 'GDH' only in the scheme; the product stereochemistry (alcohol configuration, and cis/trans for BMT-238442) was not reported. Source: SI Table S2."
},
"workups": [
{
"type": "ADDITION",
"details": "internal standard solution added; plate resealed and shaken 15 min",
"duration": {
"value": 15,
"units": "MINUTE"
},
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "1,3,5-trimethoxybenzene"
},
{
"type": "SMILES",
"value": "COc1cc(OC)cc(OC)c1"
}
],
"amount": {
"moles": {
"value": 6,
"units": "MICROMOLE"
}
},
"reaction_role": "INTERNAL_STANDARD"
},
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 800,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "ALIQUOT",
"details": "200 uL aliquot transferred to a 1 mL 96-well collection plate",
"amount": {
"volume": {
"value": 200,
"units": "MICROLITER"
}
}
},
{
"type": "ADDITION",
"details": "diluted with 300 uL MeCN:water (4:1) for UPLC-MS",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "SMILES",
"value": "CC#N"
}
],
"amount": {
"volume": {
"value": 240,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "NAME",
"value": "water"
},
{
"type": "SMILES",
"value": "O"
}
],
"amount": {
"volume": {
"value": 60,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "NAME",
"value": "6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol"
},
{
"type": "SMILES",
"value": "OC1CCc2ncccc21"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "UPLC-MS",
"type": "CUSTOM",
"details": "UPLC UV peak-area ratio of product to internal standard (1,3,5-trimethoxybenzene), as reported in the SI table (Prod/IS); not a yield",
"uses_internal_standard": true,
"float_value": {
"value": 2.5199999809265137
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"UPLC-MS": {
"type": "LCMS",
"details": "Waters I-Class UPLC-MS, Agilent Poroshell 120 EC-C18 (2.1 x 50 mm, 1.9 um); MeCN/water + 0.05% TFA gradient; PDA 210-400 nm, low-resolution ESI+ MS. Prd:IS = product peak area / 1,3,5-trimethoxybenzene peak area.",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Bristol Myers Squibb, Chemical Process Development"
},
"city": "New Brunswick, NJ / Summit, NJ, USA",
"doi": "10.1021/acs.oprd.5c00216",
"publication_url": "https://doi.org/10.1021/acs.oprd.5c00216",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Jordan (Tokens for Progress; agent-assisted curation)",
"email": "curator@example.org"
}
},
"is_mined": false
}
} | |||||