Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 41, Pages 11023-11026Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405696
Keywords
biomimetic synthesis; chlorine; enzymes; oxidation; vanadium
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Funding
- US National Institute of Health (NIH) [R01-AI047818]
- Deutsche Forschungsgemeinschaft [TE 931/1-1]
- Alexander von Humboldt Foundation
- Swiss National Science Foundation (SNF)
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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.
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