Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 41, Pages 11019-11022Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405694
Keywords
biosynthesis; enzyme catalysis; natural products; polyketides; terpenoids
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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 polycycles merochlorin A and B are complex halogenated meroterpenoid natural products with significant antibacterial activities and are produced by the marine bacterium Streptomyces sp. strain CNH-189. Heterologously produced enzymes and chemical synthesis are employed herein to fully reconstitute the merochlorin biosynthesis in vitro. The interplay of a dedicated type III polyketide synthase, a prenyl diphosphate synthase, and an aromatic prenyltransferase allow formation of a highly unusual aromatic polyketide-terpene hybrid intermediate which features an unprecedented branched sesquiterpene moiety from isosesquilavandulyl diphosphate. As supported by in vivo experiments, this precursor is furthermore chlorinated and cyclized to merochlorin A and isomeric merochlorin B by a single vanadium-dependent haloperoxidase, thus completing the remarkably efficient pathway.
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