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One-pot enzymatic synthesis of merochlorin A and B.
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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ID |
4636427 |
Author(s) |
Teufel, Robin; Kaysser, Leonard; Villaume, Matthew T; Diethelm, Stefan; Carbullido, Mary K; Baran, Phil S; Moore, Bradley S |
Author(s) at UniBasel |
Teufel, Robin
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Year |
2014 |
Title |
One-pot enzymatic synthesis of merochlorin A and B. |
Journal |
Angewandte Chemie (International ed. in English) |
Volume |
53 |
Number |
41 |
Pages / Article-Number |
11019-22 |
Keywords |
biosynthesis; enzyme catalysis; natural products; polyketides; terpenoids |
Mesh terms |
Bacterial Proteins, metabolism; Cyclization; Hemiterpenes, chemistry; Organophosphorus Compounds, chemistry; Sesterterpenes, biosynthesis, chemistry; Streptomyces, metabolism; Terpenes, chemistry |
Abstract |
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. |
ISSN/ISBN |
1521-3773 |
Full Text on edoc |
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Digital Object Identifier DOI |
10.1002/anie.201405694 |
PubMed ID |
http://www.ncbi.nlm.nih.gov/pubmed/25115835 |
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