Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger

被引:64
作者
Girol, Christian Gil [1 ]
Fisch, Katja M. [2 ]
Heinekamp, Thorsten [4 ]
Guenther, Stefan [1 ]
Huettel, Wolfgang [1 ]
Piel, Joern [3 ]
Brakhage, Axel A. [4 ]
Mueller, Michael [1 ]
机构
[1] Univ Freiburg, Inst Pharmazeut Wissensch, D-79104 Freiburg, Germany
[2] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[3] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
[4] Leibniz Inst Nat Prod Res & Infect Biol, Dept Mol & Appl Microbiol, D-07745 Jena, Germany
关键词
biaryls; biosynthesis; C?C coupling; natural products; polyketides; DIRIGENT PROTEIN; BICOUMARINS; KOTANIN; BIOSYNTHESIS; METABOLITES; SCLEROTIA; PRODUCTS; LACCASE; GENES;
D O I
10.1002/anie.201203603
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide-synthase-derived (PKS) 7-demethylsiderin. A combined approach, comprising bioinformatics and gene-deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio- and stereoselective phenol coupling reaction. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9788 / 9791
页数:4
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