ArticleJournal of the American Chemical Society2018
Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 52 citations in OpenAlex.
- Engineered Flavin-Dependent Halogenases Catalyze C-C Bond Formation via Enantioselective Semipinacol Rearrangement.Journal of the American Chemical Society · 2026Article
- Identifying and Engineering Flavin Dependent Halogenases for Selective Biocatalysis.Accounts of chemical research · 2024Article
- Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases.Angewandte Chemie (International ed. in English) · 2024Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Amino Acid-Derived Ionic Chiral Catalysts Enable Desymmetrizing Cross-Coupling to Remote Acyclic Quaternary Stereocenters.Journal of the American Chemical Society · 2023Article
- Asymmetric catalysis by flavin-dependent halogenases.Chirality · 2023Review
- Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters.Chemical science · 2023Article
- The Single-Component Flavin Reductase/Flavin-Dependent Halogenase AetF is a Versatile Catalyst for Selective Bromination and Iodination of Arenes and Olefins.Angewandte Chemie (International ed. in English) · 2022Article
- Expanding the Reactivity of Flavin Dependent Halogenases Toward Olefins via Enantioselective Intramolecular Haloetherification and Chemoenzymatic Oxidative Rearrangements.ACS catalysis · 2022Article
- Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3Journal of the American Chemical Society · 2022Article
- Reaction pathway engineering converts a radical hydroxylase into a halogenase.Nature chemical biology · 2022Article
- Distal Ionic Substrate-Catalyst Interactions Enable Long-Range Stereocontrol: Access to Remote Quaternary Stereocenters through a Desymmetrizing Suzuki-Miyaura Reaction.Journal of the American Chemical Society · 2022Article
- Engineered RebH Halogenase Variants Demonstrating a Specificity Switch from Tryptophan towards Novel Indole Compounds.Chembiochem : a European journal of chemical biology · 2021Article
- Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021Review
- Flavin-dependent halogenases catalyze enantioselective olefin halocyclization.Nature communications · 2021Article
- Synthetic C6-Functionalized Aminoflavin Catalysts Enable Aerobic Bromination of Oxidation-Prone Substrates.Angewandte Chemie (International ed. in English) · 2020Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Site-Selective C-H Halogenation Using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling.ACS central science · 2019Article
- Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity.Accounts of chemical research · 2019Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Extensive effort has been devoted to engineering flavin-dependent halogenases (FDHs) with improved stability, expanded substrate scope, and altered regioselectivity. Here, we show that variants of rebeccamycin halogenase (RebH) catalyze enantioselective desymmetrization of methylenedianilines via halogenation of these substrates distal to their pro-stereogenic center. Structure-guided engineering was used to increase the conversion and selectivity of these reactions, and the synthetic utility of the halogenated products was shown via conversion of to a chiral α-substituted indole. These results constitute the first reported examples of asymmetric catalysis by FDHs.
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