Regiodivergent NC and NN Aryl Coupling Reactions of Indoloterpenes and Cycloether Formation Mediated by a Single Bacterial Flavoenzyme

被引：73
作者：
Baunach, Martin [1 ]
Ding, Ling [1 ]
Bruhn, Torsten [2 ]
Bringmann, Gerhard [2 ]
Hertweck, Christian [1 ,3 ]
机构：
[1] HKI, Leibniz Inst Nat Prod Res & Infect Biol, Dept Biomol Chem, D-07745 Jena, Germany
[2] Univ Wurzburg, Inst Organ Chem, Wurzburg, Germany
[3] Univ Jena, Chair Nat Prod Chem, D-07745 Jena, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 34期
关键词：
alkaloids; aryl coupling; flavoproteins; indolosesquiterpenes; radicals; ALKALOIDS; INDOLOSESQUITERPENE; XIAMYCIN;
D O I：
10.1002/anie.201303733
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Radical diversification: Through the discovery of diverse indolosesquiterpene dimers in a strain heterologously expressing the xiamycin biosynthesis genes, the analysis of mutants, and biotransformation studies, it has been inferred that a single flavoprotein mediates N-C and N-N aryl coupling reactions, as well as the formation of a cyclic ether (oxiamycin). Synthetic emulation of this unusual transformation provides evidence for a radical-based mechanism. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9040 / 9043
页数：4
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