Biosynthesis of Sordarin Revealing a Diels-Alderase for the Formation of the Norbornene Skeleton
文献类型： 外文期刊
作者： Liu, Shuang He 1 ; Sun, Jia Li 1 ; Hu, Yi Ling 1 ; Zhang, Li 1 ; Zhang, Xuan 1 ; Yan, Zhang Yuan 1 ; Guo, Xing 1 ; Guo, Zhi Kai 2 ; Jiao, Rui Hua 1 ; Zhang, Bo 1 ; Tan, Ren Xiang 1 ; Ge, Hui Ming 1 ;
作者机构： 1.Nanjing Univ, Chem & Biomed Innovat Ctr ChemBIC, State Key Lab Pharmaceut Biotechnol, Inst Funct Biomol,Sch Life Sci, Nanjing 210023, Peoples R China
2.Chinese Acad Trop Agr Sci, Key Lab Biol & Genet Resources Trop Crops, Inst Trop Biosci & Biotechnol, Minist Agr, Haikou 571101, Hainan, Peoples R China
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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