ArticleJournal of the American Chemical Society2024
Biocatalytic Synthesis of α-Amino Esters via Nitrene C-H Insertion.
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 14 papers.
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Who cites it
14 citing papers in PubMed.
- Reaction Pathway and Axial Ligand Effects of C(spJACS Au · 2026Article
- Enantiodivergent Carbon-Phosphorus Bond Formation via Enzymatic Carbene Insertion.Journal of the American Chemical Society · 2026Article
- Nitrene generation and transfer for unnatural biosynthesis in living cells.Nature chemistry · 2026Article
- Engineering Enantiocomplementary Protoglobins for Stereoconvergent Construction ofJournal of the American Chemical Society · 2026Article
- Highly stereoselective synthesis of allylic β-lactamsChemical science · 2026Article
- Biocatalytic Radical C(spResearch square · 2026Article
- Reprogramming Imine Reductases for Enantioselective Reduction of Electron-Rich Enamides.JACS Au · 2026Article
- Nonheme Fe Enzyme-Catalyzed Enantiodivergent Nitrogen Migration: Directed Evolution and Computational Study of Isopenicillin N Synthases for Biocatalytic Synthesis of Arylglycines.Angewandte Chemie (International ed. in English) · 2026Article
- Enzyme Engineering Database (EnzEngDB): a platform for sharing and interpreting sequence-function relationships across protein engineering campaigns.Nucleic acids research · 2026Article
- Biocatalytic Synthesis of N-Protected α-Amino Acids through 1,3-Nitrogen Migration by Nonheme Iron Enzymes.Journal of the American Chemical Society · 2025Article
- Metabolic Engineering of the 5-Aminolevulinate Biosynthetic Pathway in E. coli Improves Efficiency of Hemoprotein-Based Biocatalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Enzymatic Stereodivergent Synthesis of Azaspiro[2.y]alkanes.Journal of the American Chemical Society · 2025Article
- Direct, Convergent α-Amidation of β-Keto Esters via Nickelocene Catalysis.Organic letters · 2025Article
- Mechanistic and Computational Insights into Asymmetric Intramolecular Iron-Catalyzed Nitrene Transfer into Benzylic C─H Bonds.ACS catalysis · 2025Article
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6 authors.
Funding
Abstract
α-Amino esters are precursors to noncanonical amino acids used in developing small-molecule therapeutics, biologics, and tools in chemical biology. α-C-H amination of abundant and inexpensive carboxylic acid esters through nitrene transfer presents a direct approach to α-amino esters. Methods for nitrene-mediated amination of the protic α-C-H bonds in carboxylic acid esters, however, are underdeveloped. This gap arises because hydrogen atom abstraction (HAA) of protic C-H bonds by electrophilic metal-nitrenoids is slow: metal-nitrenoids preferentially react with polarity-matched, hydridic C-H bonds, even when weaker protic C-H bonds are present. This study describes the discovery and evolution of highly stable protoglobin nitrene transferases that catalyze the enantioselective intermolecular amination of the α-C-H bonds in carboxylic acid esters. We developed a high-throughput assay to evaluate the activity and enantioselectivity of mutant enzymes together with their sequences using the Every Variant Sequencing (evSeq) method. The assay enabled the identification of enantiodivergent enzymes that function at ambient conditions in
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