ArticleAngewandte Chemie (International ed. in English)2021
Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed, 27 citations in OpenAlex.
- A pyridoxal phosphate-dependent enzyme platform for stereoselective synthesis of γ-tertiary-nitro-noncanonical amino acids.Nature communications · 2026Article
- Integrating microbial cell factory with new-to-nature photobiocatalysis for de novo biosynthesis of D-homotryptophan.Nature communications · 2026Article
- A pyridoxal radical carboligase and imine reductase photobiocatalytic cascade for stereoselective synthesis of unnatural prolines.Nature chemistry · 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
- α-Hydrazino Acids Inhibit Pyridoxal Phosphate-Dependent Decarboxylases via "Catalytically Correct" Ketoenamine Tautomers: A Special Motif for Chemical Biology and Drug Discovery?ACS catalysis · 2025Article
- Biocatalytic asymmetric aldol addition into unactivated ketones.Nature chemistry · 2024Article
- The β-subunit of tryptophan synthase is a latent tyrosine synthase.Nature chemical biology · 2024Article
- Molecular and Structural Basis for Cγ-C Bond Formation by PLP-Dependent Enzyme Fub7.Angewandte Chemie (International ed. in English) · 2024Article
- Biocatalytic Construction of Chiral Pyrrolidines and Indolines via Intramolecular C(spACS central science · 2023Article
- Engineered Biocatalytic Synthesis of β-N-Substituted-α-Amino Acids.Angewandte Chemie (International ed. in English) · 2023Article
- Multiplexed Assessment of Promiscuous Non-Canonical Amino Acid Synthase Activity in a Pyridoxal Phosphate-Dependent Protein Family.ACS catalysis · 2023Article
- New Additions to the Arsenal of Biocatalysts for Noncanonical Amino Acid Synthesis.Current opinion in green and sustainable chemistry · 2022Article
- Asymmetric Alkylation of Cyclic Ketones with Dehydroalanine via H-Bond-Directing Enamine Catalysis: Straightforward Access to Enantiopure Unnatural α-Amino Acids.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Biocatalytic Friedel-Crafts Reactions.ChemCatChem · 2022Review
- Investigation of β-Substitution Activity of O-Acetylserine Sulfhydrolase from Citrullus vulgaris.Chembiochem : a European journal of chemical biology · 2022Article
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6 authors at 2 institutions in 1 country.
Funding
Abstract
The β-subunit of tryptophan synthase (TrpB) catalyzes a PLP-mediated β-substitution reaction between indole and serine to form L-Trp. A succession of TrpB protein engineering campaigns to expand the enzyme's nucleophile substrate range has enabled the biocatalytic production of diverse non-canonical amino acids (ncAAs). Here, we show that ketone-derived enolates can serve as nucleophiles in the TrpB reaction to achieve the asymmetric alkylation of ketones, an outstanding challenge in synthetic chemistry. We engineered TrpB by directed evolution to catalyze the asymmetric alkylation of propiophenone and 2-fluoroacetophenone with a high degree of selectivity. In reactions with propiophenone, preference for the opposite product diastereomer emerges over the course of evolution, demonstrating that full control over the stereochemistry at the new chiral center can be achieved. The addition of this new reaction to the TrpB platform is a crucial first step toward the development of efficient methods to synthesize non-canonical prolines and other chirally dense nitrogen heterocycles.
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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.