ArticleJournal of the American Chemical Society2024
Threonine Aldolase-Catalyzed Enantioselective α-Alkylation of Amino Acids through Unconventional Photoinduced Radical Initiation.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Article
- Catalytically Promiscuous PLP-Dependent Aminotransferases Are Biocatalysts for C-C Bond Formation.ACS central science · 2026Article
- Emerging enzymatic strategies for the synthesis of α-tertiary amino acids.Communications chemistry · 2026Review
- Reprogramming Imine Reductases for Enantioselective Reduction of Electron-Rich Enamides.JACS Au · 2026Article
- Engaging Unstabilized Alkyl Radicals with Pyridoxal Radical Biocatalysis: Enantiodivergent Synthesis of Aliphatic Non-Canonical Amino Acids.bioRxiv : the preprint server for biology · 2026Article
- Designing and Engineering Enzymes for New-to-Nature Photobiocatalysis.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Biocatalytic Synthesis of N-Protected α-Amino Acids through 1,3-Nitrogen Migration by Nonheme Iron Enzymes.Journal of the American Chemical Society · 2025Article
- Mechanistic and Structural Analyses of Non-Heme Iron Enzyme TqaM for α-Tertiary Amino Acid Synthesis.Journal of the American Chemical Society · 2025Article
- Diversity-oriented photobiocatalytic synthesis via stereoselective three-component radical coupling.Science (New York, N.Y.) · 2025Article
- Enantioselective Radical Hydrocyanoalkylation of Alkenes via Photoenzymatic Catalysis.JACS Au · 2025Article
- Profiling of Diverse Pyridoxal-5'-Phosphate Dependent Enzymes Reveals Promiscuous Aldolase Activity with (2-Azaaryl)methanamines.Journal of the American Chemical Society · 2025Article
- Cooperative Photometallobiocatalysis: Nonheme Fe Enzyme-Catalyzed Enantioconvergent Radical Decarboxylative Azidation, Thiocyanation, and Isocyanation of Redox-Active Esters.Angewandte Chemie (International ed. in English) · 2025Article
- Designing Enzymatic Reactivity with an Expanded Palette.Chembiochem : a European journal of chemical biology · 2025Review
- Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon-Carbon Bond Construction.Molecules (Basel, Switzerland) · 2025Review
- Catalytic Enantioselective Smiles Rearrangement Enabled by the Directed Evolution of P450 Radical Aryl Migratases.Journal of the American Chemical Society · 2025Article
- Threonine aldolase-catalyzed stereoselective radical α-alkylation of amino acids.Methods in enzymology · 2025Article
- Stabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Asymmetric Synthesis of 2-Arylethylamines: A Metal-Free Review of the New Millennium.Molecules (Basel, Switzerland) · 2024Review
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Abstract
Visible light-driven pyridoxal radical biocatalysis has emerged as a promising strategy for the stereoselective synthesis of valuable noncanonical amino acids (ncAAs). Previously, the use of well-tailored photoredox catalysts represented the key to enable efficient pyridoxal phosphate (PLP) enzyme-catalyzed radical reactions. Here, we report a PLP-dependent threonine aldolase-catalyzed asymmetric α-C-H alkylation of abundant amino acids using Katritzky pyridinium salts as alkylating agents. The use of engineered threonine aldolases allowed for this redox-neutral radical alkylation to proceed efficiently, giving rise to challenging α-trisubstituted and -tetrasubstituted ncAA products in a protecting-group-free fashion with excellent enantiocontrol. Mechanistically, this enantioselective α-alkylation capitalizes on the unique reactivity of the persistent enzymatic quinonoid intermediate derived from the PLP cofactor and the amino acid substrate to allow for novel radical C-C coupling. Surprisingly, this photobiocatalytic process does not require the use of well-established photoredox catalysts and operates through an unconventional photoinduced radical generation involving a PLP-derived aldimine. The ability to develop photobiocatalytic reactions without relying on classic photocatalysts or photoenzymes opens up new avenues for advancing stereoselective intermolecular radical reactions that are not known in either organic chemistry or enzymology.
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