Biosynthesis of Sordarin Revealing a Diels-Alderase for the Formation of the Norbornene Skeleton

文献类型： 外文期刊

第一作者： Liu, Shuang He

作者： Liu, Shuang He;Sun, Jia Li;Hu, Yi Ling;Zhang, Li;Zhang, Xuan;Yan, Zhang Yuan;Guo, Xing;Jiao, Rui Hua;Zhang, Bo;Tan, Ren Xiang;Ge, Hui Ming;Guo, Zhi Kai

作者机构：

关键词： Biosynthesis; Diels-Alderase; Glycosides; Heterologous Expression; Terpenoids

期刊名称：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION （ 影响因子：16.823； 五年影响因子：15.311 ）

ISSN： 1433-7851

年卷期： 2022 年 61 卷 33 期

页码：

收录情况： SCI

摘要： Sordarin (1) is a fungal diterpene glycoside that displays potent antifungal bioactivity through inhibition of elongation factor 2. The structures of sordarin and related compounds feature a highly rearranged tetracyclic diterpene core. In this study, we identified a concise pathway in the biosynthesis of sordarin. A diterpene cyclase (SdnA) generates the 5/8/5 cycloaraneosene framework, which is decorated by a set of P450s that catalyze a series of oxidation reactions, including hydroxylation, desaturation, and C-C bond oxidative cleavage, to give a carboxylate intermediate with a terminal alkene and a cyclopentadiene moiety. A novel Diels-Alderase SdnG catalyzes an intramolecular Diels-Alder (IMDA) reaction on this intermediate to forge the sordarin core structure. Subsequent methyl hydroxylation and glycosylation complete the biosynthesis of sordarin. Our work discloses a new strategy used by nature for the formation of the rearranged diterpene skeleton.

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