Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase

被引：40

作者：

Harris, Nicholas C. ^{[3
]}

Born, David A. ^{[4
,5
]}

Cai, Wenlong ^{[1
]}

Huang, Yaobing ^{[1
]}

Martin, Joelle ^{[6
]}

Khalaf, Ryan ^{[6
]}

Drennan, Catherine L. ^{[4
,7
,8
]}

Zhang, Wenjun ^{[1
,2
]}

机构：

[1] Univ Calif Berkeley, Dept Chem & Biomol Engn, Berkeley, CA 94720 USA

[2] Chan Zuckerberg Biohub, San Francisco, CA 94158 USA

[3] Univ Calif Berkeley, Dept Plant & Microbial Biol, Berkeley, CA 94720 USA

[4] MIT, Dept Biol, Cambridge, MA USA

[5] Harvard Univ, Grad Program Biophys, Cambridge, MA 02138 USA

[6] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[7] MIT, Howard Hughes Med Inst, Cambridge, MA 02139 USA

[8] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 31期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

acyl-acyl carrier protein ligase; biosynthesis; isocyanide; oxidoreductase; protein structures; TAURINE/ALPHA-KETOGLUTARATE DIOXYGENASE; ESCHERICHIA-COLI; PSEUDOMONAS-AERUGINOSA; BIOSYNTHESIS; MECHANISM; INSIGHT; GLYCINE; GENES; IRON;

D O I：

10.1002/anie.201804307

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The electron-rich isonitrile is an important functionality in bioactive natural products, but its biosynthesis has been restricted to the IsnA family of isonitrile synthases. We herein provide the first structural and biochemical evidence of an alternative mechanism for isonitrile formation. ScoE, a putative non-heme iron(II)-dependent enzyme from Streptomyces coeruleorubidus, was shown to catalyze the conversion of (R)-3-((carboxymethyl)amino)butanoic acid to (R)-3-isocyanobutanoic acid through an oxidative decarboxylation mechanism. This work further provides a revised scheme for the biosynthesis of a unique class of isonitrile lipopeptides, of which several members are critical for the virulence of pathogenic mycobacteria.

引用

页码：9707 / 9710

页数：4

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