ArticleJournal of the American Chemical Society2023
Diversifying Amino Acids and Peptides via Deaminative Reductive Cross-Couplings Leveraging High-Throughput Experimentation.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 71 citations in OpenAlex.
- Advancing Drug Discovery through Academia-Industry Collaborations: Lessons from Merck Discovery Chemistry Partnerships.ACS central science · 2026Review
- Accelerated Synthesis of Novel Indole-3-Sulfonamides Leveraging High-Throughput Experimentation.ACS medicinal chemistry letters · 2026Article
- Late-Stage Functionalization of Peptides on the Solid Phase.Angewandte Chemie (International ed. in English) · 2026Review
- Photoredox-Catalyzed Lysine C(spJournal of the American Chemical Society · 2026Article
- Potassium Bisulfite's Role in Developing a Robust Platform for EnantioenrichedJournal of the American Chemical Society · 2026Article
- Radical/Ylide-Tunable Pyridinium Salt Enables Photo/Thermocatalytic Divergent [3 + 2] Cycloadditions.JACS Au · 2026Article
- Article
- Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026Article
- Palladium-Catalyzed Deaminative Cross-Coupling of Alkyl Nitroso Carbamates.ACS catalysis · 2026Article
- Article
- Late-Stage Serine Modification Enables Noncanonical Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Direct Editing of Cysteine to Electrophilic Alkyl Halides in Peptides.Journal of the American Chemical Society · 2025Article
- Nickel-mediated aerobic C(sp2)-nucleophile coupling reactions for late-stage diversification of aryl electrophiles.Nature synthesis · 2025Article
- A stereodynamic probe of Pt(II) molecular hinge for chiroptical sensing of cryptochiral compounds.Nature communications · 2025Article
- Heterocyclic Assembly: An Underutilized Disconnection with Potential to Maximize High FspACS medicinal chemistry letters · 2025Article
- Late-stage installation and functionalization of alkyl pyridiniums: a general HTE amenable strategy to access diverse aryl alanine containing macrocyclic peptides.Chemical science · 2025Article
- A versatile route towards 6-arylpipecolic acids.Beilstein journal of organic chemistry · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalysed cross-electrophile coupling.Nature chemistry · 2024Article
- Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides.The Journal of organic chemistry · 2024Article
Corrections and comments
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
Abstract
A deaminative reductive coupling of amino acid pyridinium salts with aryl bromides has been developed to enable efficient synthesis of noncanonical amino acids and diversification of peptides. This method transforms natural, commercially available lysine, ornithine, diaminobutanoic acid, and diaminopropanoic acid to aryl alanines and homologated derivatives with varying chain lengths. Attractive features include ability to transverse scales, tolerance of pharma-relevant (hetero)aryls and biorthogonal functional groups, and the applicability beyond monomeric amino acids to short and macrocyclic peptide substrates. The success of this work relied on high-throughput experimentation to identify complementary reaction conditions that proved critical for achieving the coupling of a broad scope of aryl bromides with a range of amino acid and peptide substrates including macrocyclic peptides.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.