A multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins

TitleA multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins
Publication TypeJournal Article
Year of Publication2014
AuthorsDiethelm S., Teufel R., Kaysser L., Moore BS
JournalAngewandte Chemie-International Edition
Volume53
Pagination11023-11026
Date Published2014/10
Type of ArticleArticle
ISBN Number1433-7851
Accession NumberWOS:000342758200037
Keywordsacceptor type interactions; aromatic series; biomimetic synthesis; biosynthesis; bromoperoxidase; chlorine; enzymes; halogenation; haloperoxidases; marine natural-products; ortho-chlorination; oxidation; phenols; regioselective; sulfuryl chloride; vanadium
Abstract

The vanadium-dependent chloroperoxidase Mcl24 was discovered to mediate a complex series of unprecedented transformations in the biosynthesis of the merochlorin meroterpenoid antibiotics. In particular, a site-selective naphthol chlorination is followed by an oxidative dearomatization/terpene cyclization sequence to build up the stereochemically complex carbon framework of the merochlorins in one step. Inspired by the enzyme reactivity, a chemical chlorination protocol paralleling the biocatalytic process was developed. These chemical studies led to the identification of previously overlooked merochlorin natural products.

DOI10.1002/anie.201405696
Short TitleAngew. Chem.-Int. Edit.
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