Resorcylic Acid Lactone Biosynthesis Relies on a Stereotolerant Macrocyclizing Thioesterase

被引：22

作者：

Heberlig, Graham W. ^{[1
]}

Wirz, Monica ^{[1
]}

Wang, Meng ^{[1
]}

Boddy, Christopher N. ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 22期

基金：

加拿大自然科学与工程研究理事会;

关键词：

POLYKETIDE SYNTHASE GENES; CHEMOENZYMATIC SYNTHESIS; STRUCTURAL BASIS; DOMAIN; HYDROLYSIS; RADICICOL; MACROLACTONIZATION; HYPOTHEMYCIN; ZEARALENONE; INHIBITION;

D O I：

10.1021/ol502747t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zearalenone and radicicol are highly related resorcylic acid lactones with the rare property of having opposite stereochemical configurations of the secondary alcohol involved in lactone formation. The ability of the thioesterases from the zearalenone and radicicol biosynthetic pathways to macrocyclize both d and l configured synthetic substrate analogs was biochemically characterized and showed that both enzymes were highly stereotolerant, macrocyclizing both substrates with similar kinetic parameters. This observed stereotolerance is consistent with a proposed evolution of both natural products from a common ancestral resorcylic acid lactone.

引用

页码：5858 / 5861

页数：4

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