Biocatalytic C14-Hydroxylation on Androstenedione Enabled Modular Synthesis of Cardiotonic Steroids
文献类型： 外文期刊
作者： Zhao, Yang 1 ; Zhang, Bo 1 ; Sun, Zi Qian 1 ; Zhang, Hao 2 ; Wang, Wen 1 ; Wang, Zi Ru 1 ; Guo, Zhi Kai 3 ; Yu, Shouyun 2 ; Tan, Ren Xiang 1 ; Ge, Hui Ming 1 ;
作者机构： 1.Nanjing Univ, Sch Life Sci, Chem & Biomed Innovat Ctr ChemBIC, Inst Funct Biomol,State Key Lab Pharmaceut Biotec, Nanjing 210023, Peoples R China
2.Nanjing Univ, Chem & Biomed Innovat Ctr ChemBIC, State Key Lab Analyt Chem Life Sci, Jiangsu Key Lab Adv Organ Mat,Sch Chem & Chem Eng, Nanjing 210023, Peoples R China
3.Chinese Acad Trop Agr Sci, Minist Agr, Inst Trop Biosci & Biotechnol, Key Lab Biol & Genet Resources Trop Crops, Haikou 571101, Peoples R China
关键词： cardiotonic steroid; P450; biocatalysis; bufotalin; digitoxigenin
期刊名称：ACS CATALYSIS （ 影响因子：13.7； 五年影响因子：14.413 ）
ISSN： 2155-5435
年卷期： 2022 年 12 卷 16 期
页码：
收录情况： SCI
摘要： Cardiotonic steroids are a unique class of natural products, possessing a steroid framework with a characteristic hydroxyl group at C14 and a beta-oriented five- or six-membered unsaturated lactone substituent at C17. Installation of a hydroxyl group at the C14 position by direct C-H hydroxylation is proved to be challenging through chemical transformation. Herein, we report the identification of two P450 enzymes, CYP11411 and CYP44476, each of which can convert androstenedione (AD) to 14 alpha-OH-AD directly, from the plant Calotropis gigantea and the toad Bufo gargarizans, respectively. The obtained 14 alpha-OH-AD can then be chemically converted to a key 14 beta-OH steroid intermediate, which serves as a basis for the total synthesis of cardiotonic steroids including bufotalin, bufogenin B, and digitoxigenin by the modular installation of a five- or six-membered lactone ring at the C17 position.
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