Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process

被引：42

作者：

Schwarzer, Darius D. ^{[1
]}

Gritsch, Philipp J. ^{[1
]}

Gaich, Tanja ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 46期

关键词：

biosynthesis; Cope rearrangement; indole prenylation; oxindole; reaction mechanisms; ERGOT ALKALOID BIOSYNTHESIS; (-)-N-METHYLWELWITINDOLINONE C ISONITRILE; ELECTROPHILIC SUBSTITUTION; CHORISMATE MUTASE; TRANSITION-STATE; CATALYZED REARRANGEMENT; INDOLE-DERIVATIVES; MODEL; WELWITINDOLINONES; TRYPTOPHAN;

D O I：

10.1002/anie.201203586

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Easy to cope with: Experimental evidence was found to support an enzymatic [3,3]-sigmatropic rearrangement catalyzed by dimethylallyltryptophan (DMAT) synthase (see scheme). A bio-inspired system showed the feasibility of Cope rearrangement to the C-4 position of the indole nucleus. The tricyclic benzo[cd]indole core of welwitindolinones and dragmacidin-E was synthesized using this transformation. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11514 / 11516

页数：3

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