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A multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins.
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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ID |
4636425 |
Author(s) |
Diethelm, Stefan; Teufel, Robin; Kaysser, Leonard; Moore, Bradley S |
Author(s) at UniBasel |
Teufel, Robin
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Year |
2014 |
Title |
A multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins. |
Journal |
Angewandte Chemie (International ed. in English) |
Volume |
53 |
Number |
41 |
Pages / Article-Number |
11023-6 |
Keywords |
biomimetic synthesis; chlorine; enzymes; oxidation; vanadium |
Mesh terms |
Biocatalysis; Chloride Peroxidase, metabolism; Cyclization; Oxidation-Reduction; Sesterterpenes, biosynthesis, chemistry; Stereoisomerism |
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. |
ISSN/ISBN |
1521-3773 |
Full Text on edoc |
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Digital Object Identifier DOI |
10.1002/anie.201405696 |
PubMed ID |
http://www.ncbi.nlm.nih.gov/pubmed/25147132 |
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25/04/2024
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