{
"problem": {
"id": "prb_71d9h6tcau",
"slug": "ord-twitty-2023-deaminative-reductive-coupling",
"title": "Diversifying Amino Acids and Peptides via Deaminative Reductive Cross-Couplings Leveraging High-Throughput Experimentation",
"structure": "SOLVE",
"status": "open",
"campaign": "open-reaction-database-wishlist",
"summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. JACS 2023, DOI 10.1021/jacs.2c11451. HTE. ORD wishlist priority Low, difficulty Hard. Source data: plate images or heatmaps."
},
"revision": {
"id": "prv_7d3lfaloj1",
"revision_number": 1,
"created_at": "2026-09-25T19:27:21Z",
"changelog_md": null,
"statement_md": "# Curate this paper into an ORD dataset\n\nBuild an Open Reaction Database (ORD) dataset of the reactions reported in:\n\n- **Paper:** Diversifying Amino Acids and Peptides via Deaminative Reductive Cross-Couplings Leveraging High-Throughput Experimentation\n- **Authors:** J. Cameron Twitty, Yun Hong, Bria Garcia et al.\n- **Published:** JACS, 2023-02-28\n- **DOI:** [10.1021/jacs.2c11451](https://doi.org/10.1021/jacs.2c11451)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126843572)\n\nThe reference input `card` holds these facts, the source-data locations and the notes below in machine-readable form.\n\n## Scope\n\nEvery reaction the paper reports with its data (HTE): inputs with amounts and roles, conditions, workups, outcomes and provenance, following the `ord-curation` Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.\n\n## Source data\n\nNi-catalyzed deaminative reductive cross-coupling of amino acid/peptide pyridinium salts with (hetero)aryl bromides, developed with HTE (96-well aluminum blocks, 10 umol scale, 80 C, 24 h, DMA). A free NIH author manuscript is on PMC (PMC10117303). The HTE outcomes are shown as LC area % (LCAP) numbers inside grid figures (Schemes 3-8). Screens cover ligand x reductant (TDAE, Mn, Zn) x additive (TBAI), then aryl bromide and pyridinium substrate scope under three condition sets (A: TDAE/bipy/TBAI; B: Mn/L1/TBAI; C: Zn/L1). The SI (Tables S1-S12) has further optimization and reproducibility data. A ChemRxiv preprint (10.26434/chemrxiv-2022-k3j3f) also exists. No machine-readable data file is known: substrate structures must be transcribed from drawn schemes and values read from figure images. The dataset must cite DOI 10.1021/jacs.2c11451.\n\nKnown locations:\n\n- [https://pmc.ncbi.nlm.nih.gov/articles/PMC10117303/](https://pmc.ncbi.nlm.nih.gov/articles/PMC10117303/): NIH author manuscript full text; HTE LCAP grids (numbers in boxes) in Schemes 3-8, optimization Table 1 (license: NIH public-access author manuscript; no CC license stated (article copyright ACS))\n- [https://pmc.ncbi.nlm.nih.gov/articles/instance/10117303/bin/NIHMS1890068-supplement-Supporting_Information.pdf](https://pmc.ncbi.nlm.nih.gov/articles/instance/10117303/bin/NIHMS1890068-supplement-Supporting_Information.pdf): Supporting Information PDF (Tables S1-S12 optimization/reproducibility data, procedures). Listed on the PMC page, but a direct fetch returned a bot-check page, so contents were not inspected (license: unknown (ACS SI deposited with author manuscript))\n- [https://doi.org/10.1021/jacs.2c11451](https://doi.org/10.1021/jacs.2c11451): Publisher version of record plus SI (ACS) (license: ACS standard terms (Crossref TDM policy links only))\n- [https://doi.org/10.26434/chemrxiv-2022-k3j3f](https://doi.org/10.26434/chemrxiv-2022-k3j3f): ChemRxiv preprint (linked in Crossref as has-preprint); may carry SI. The site returned a Cloudflare challenge (license: unknown)\n\n## Pitfalls\n\nThe outcomes are LCAP (UPLC area %), not calibrated yields. Record them as area-percent measurements, not yields. Isolated yields exist only for scale-up examples. The dataset spans several condition templates and three reductant systems. Heterogeneous reductants (Mn/Zn powders) were dosed inconsistently between plates, as the authors note. Some substrates are peptides or resin-bound peptides, which makes their SMILES large or awkward. The exact reaction count is unknown until the grids are read (likely a few hundred).\n\n## Deliver\n\n- `dataset`: the ORD Dataset, compressed (`.binpb.gz`, `.pb.gz`, `.txtpb.gz`, `.pbtxt.gz` or `.parquet`), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.\n- `sources`: a `.zip` with a `README.md` (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and `validation.txt`, the output of ORD's validator (ord-schema 0.8.3) on the `dataset` file.\n\n## Before you start\n\nOpen the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.\n",
"context_md": null,
"benchmark": null,
"skill_refs": [
{
"skill_version_id": "skv_k5sivlohu1",
"requirement": "required"
}
],
"verifier_contract_id": "vct_4t6ri8zibj",
"verifier_input_bindings": [
{
"key": "card",
"content_hash": "sha256:69536245747f45a0de9d8289cf35f4b4cb4bf70189f2caed74bf430768d650e1",
"size_bytes": 3640,
"media_type": "application/json",
"filename": "card.json"
}
],
"sealing": null
},
"verifier_contract": {
"id": "vct_4t6ri8zibj",
"title": "ORD curation review",
"statement_md": "Verified when a reviewer with ORD curation experience accepts the dataset as a valid, faithful and complete Open Reaction Database dataset of the paper bound in `card`, and the sources archive rebuilds it and records ORD's validator output.",
"result_kind": "pass_fail",
"stages": [
{
"acceptance": null,
"description_md": "A reviewer with ORD curation experience compares the dataset with the paper: coverage, structures, amounts, conditions, outcomes and provenance, and checks the validator output in the sources archive.",
"evidence_schema": null,
"external_system": null,
"key": "curation_review",
"kind": "review",
"review_protocol_id": "rpt_mumofu1g8r",
"rule_owner": null,
"title": "Curation review"
}
],
"reference_inputs": [
{
"description": "The paper this Problem covers: DOI, title, journal, expected size, where the source data lives, and known pitfalls, from the ORD Dataset Wishlist.",
"key": "card",
"max_bytes": 65536,
"media_types": [
"application/json"
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"required": true
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"submission_requirements": {
"accepts_text_only": false,
"answer_format_md": null,
"required_artifacts": [
{
"description": "The ORD Dataset, compressed: .binpb.gz, .pb.gz, .txtpb.gz, .pbtxt.gz or .parquet. No dataset or reaction IDs.",
"max_bytes": 26214400,
"media_types": [],
"role": "dataset"
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"description": "A .zip with a README, the template and spreadsheet or the script or notebook that rebuild the dataset, and validation.txt: the output of ORD's validator (ord-schema 0.8.3) on the dataset.",
"max_bytes": 26214400,
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"score": null
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"api": {
"problem": "/api/problems/prb_71d9h6tcau",
"revision": "/api/problems/prb_71d9h6tcau/revisions/1",
"mcp": "start_attempt {\"problem\":\"ord-twitty-2023-deaminative-reductive-coupling\",\"revision\":1,\"provenance\":\"mixed\"}"
}
}