A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone
Feng, Ke-Na1,3; Yang, Yan-Long1; Xu, Yu-Xing1,3; Zhang, Yue1,3; Feng, Tao2; Huang, Sheng-Xiong1; Liu, Ji-Kai2; Zeng, Ying1
Corresponding AuthorHuang, Sheng-Xiong(sxhuang@mail.kib.ac.cn) ; Liu, Ji-Kai(jkliu@mail.kib.ac.cn) ; Zeng, Ying(biochem@mail.kib.ac.cn)
2020-04-27
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Volume59Issue:18Pages:7209-7213
AbstractVibralactone is isolated from the basidiomycete fungus Boreostereum vibrans as one of the strongest lipase inhibitors. Its unusual beta-lactone-fused bicycle is derived from an aryl ring moiety by an oxidative ring-expansion prior to an intramolecular cyclization. Herein, we report the discovery of the cyclase VibC which belongs to the alpha/beta-hydrolase superfamily and is involved in the vibralactone biosynthesis. Biochemical and crystal studies suggest that VibC may catalyze an aldol or an electrocyclic reaction initiated by the Ser-His-Asp catalytic triad. For the aldol and pericyclic chemistry in living cells, VibC is a unique hydrolase performing the carbocycle formation of an oxepinone to a fused bicyclic beta-lactone. This presents a naturally occurring, new enzymatic reaction in both aldol and hydrolase (bio)chemistry that will guide future exploitation of these enzymes in synthetic biology for chemical-diversity expansion of natural products.
Keywordaldol biosynthesis natural products pericyclic reactions protein structures
DOI10.1002/anie.202000710
Indexed BySCI ; SCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000526818900036
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/71523
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorHuang, Sheng-Xiong; Liu, Ji-Kai; Zeng, Ying
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.South Cent Univ Nationalities, Sch Pharmaceut Sci, Wuhan 430074, Hubei, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Feng, Ke-Na,Yang, Yan-Long,Xu, Yu-Xing,et al. A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020,59(18):7209-7213.
APA Feng, Ke-Na.,Yang, Yan-Long.,Xu, Yu-Xing.,Zhang, Yue.,Feng, Tao.,...&Zeng, Ying.(2020).A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,59(18),7209-7213.
MLA Feng, Ke-Na,et al."A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59.18(2020):7209-7213.
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