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

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.

SUBMITTER: Diethelm S

PROVIDER: S-EPMC4226426 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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

Diethelm Stefan S Teufel Robin R Kaysser Leonard L Moore Bradley S BS

Angewandte Chemie (International ed. in English) 20140821 41

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 biocatalyt ...[more]

PMID: 25147132

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