ArticleACS catalysis2022
Expanding the Reactivity of Flavin Dependent Halogenases Toward Olefins via Enantioselective Intramolecular Haloetherification and Chemoenzymatic Oxidative Rearrangements.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- 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
- Asymmetric catalysis by flavin-dependent halogenases.Chirality · 2023Review
- 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
- Directed Evolution of Flavin-Dependent Halogenases for Site- and Atroposelective Halogenation of 3-Aryl-4(3Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Of the different classes of halogenases characterized to date, flavin dependent halogenases (FDHs) are most associated with site-selective halogenation of electron rich arenes and enol(ate) moieties in the biosynthesis of halogenated natural products. This capability has made them attractive biocatalysts, and extensive efforts have been devoted to both discovering and engineering these enzymes for different applications. We have established that engineered FDHs can catalyze different enantioselective halogenation processes, including halolactonization of simple alkenes with a tethered carboxylate nucleophile. In this study, we expand the scope of this reaction to include alcohol nucleophiles and a greater diversity of alkene substitution patterns to access a variety of chiral tetrahydrofurans. We also demonstrate that FDHs can be interfaced with ketoreductases to enable halocyclization using ketone substrates in one-pot cascade reactions and that the halocyclization products can undergo subsequent rearrangements to form hydroxylated and halogenated products. Together, these advances expand the utility of FDHs for enantio- and diastereoselective olefin functionalization.
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