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A Multitasking Vanadium‐Dependent Chloroperoxidase as an Inspiration for the Chemical Synthesis of the Merochlorins
Author(s) -
Diethelm Stefan,
Teufel Robin,
Kaysser Leonard,
Moore Bradley S.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405696
Subject(s) - vanadium , chemistry , human multitasking , reactivity (psychology) , terpene , chemical synthesis , organic chemistry , combinatorial chemistry , biochemistry , biology , medicine , alternative medicine , pathology , neuroscience , in vitro
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.