ArticleCommunications chemistry2024
Site-selective chlorination of pyrrolic heterocycles by flavin dependent enzyme PrnC.
Article in Communications chemistry, 2024. 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.
- Chemoselective halogenation of premarineosin A for next-generation antimalarial development.Organic & biomolecular chemistry · 2026Article
- Metabolic engineering and late-stage functionalization expand the chemical space of the antimalarial premarineosin A.Communications chemistry · 2025Article
- Further characterization and engineering of an 11-amino acid motif for enhancing recombinant soluble protein expression.Microbial cell factories · 2025Article
- Chemoenzymatic synthesis.Communications chemistry · 2025Article
- Crystallographic and Thermodynamic Evidence of Negative Coupling in the Flavin-Dependent Tryptophan Halogenases AbeH and BorH.ACS omega · 2025Article
- Further Characterization of Fungal Halogenase RadH and Its Homologs.Biomolecules · 2023Article
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Authors and funding
15 authors.
Funding
Abstract
Halogenation of pyrrole requires strong electrophilic reagents and often leads to undesired polyhalogenated products. Biocatalytic halogenation is a highly attractive approach given its chemoselectivity and benign reaction conditions. While there are several reports of enzymatic phenol and indole halogenation in organic synthesis, corresponding reports on enzymatic pyrrole halogenation have been lacking. Here we describe the in vitro functional and structural characterization of PrnC, a flavin-dependent halogenase that can act on free-standing pyrroles. Computational modeling and site mutagenesis studies identified three key residues in the catalytic pocket. A moderate resolution map using single-particle cryogenic electron microscopy reveals PrnC to be a dimer. This native PrnC can halogenate a library of structurally diverse pyrrolic heterocycles in a site-selective manner and be applied in the chemoenzymatic synthesis of a chlorinated analog of the agrochemical fungicide Fludioxonil.
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Registered trials
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