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An NADPH-Dependent Ketoreductase Catalyses the Tetracyclic to Pentacyclic Skeletal Rearrangement in Chartreusin Biosynthesis

文献类型： 外文期刊

作者： Jiao, Fang Wen 1 ; Wang, Yi Shuang 1 ; You, Xue Ting 1 ; Wei, Wanqing 3 ; Chen, Yu 3 ; Yang, Cheng Long 1 ; Guo, Zhi K 1 ;

作者机构： 1.Nanjing Univ, Sch Life Sci, Chem & Biomed Innovat Ctr, Inst Funct Biomol,State Key Lab Pharmaceut Biotec, Nanjing 210023, Peoples R China

2.Nanjing Univ Chinese Med, State Key Lab Cultivat Base TCM Qual & Efficacy, Nanjing 210046, Peoples R China

3.Nanjing Univ, Sch Chem & Chem Engn, Chem & Biomed Innovat Ctr, Jiangsu Key Lab Adv Organ Mat,State Key Lab Coord, Nanjing 210023, Peoples R China

4.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Key Lab Biol & Genet Resources Trop Crops, Minist Agr, Haikou 571101, Hainan, Peoples R China

关键词： Baeyer-Villiger monooxidase; biosynthesis; chartreusin; ketoreductase; skeletal rearrangement

期刊名称：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION （ 影响因子：15.336； 五年影响因子：14.205 ）

ISSN： 1433-7851

年卷期： 2021 年 60 卷 50 期

页码：

收录情况： SCI

摘要： Redox tailoring enzymes play key roles in generating structural complexity and diversity in type II polyketides. In chartreusin biosynthesis, the early C-13-labeling experiments and bioinformatic analysis suggest the unusual aglycone is originated from a tetracyclic anthracyclic polyketide. Here, we demonstrated that the carbon skeleton rearrangement from a linear anthracyclic polyketide to an angular pentacyclic biosynthetic intermediate requires two redox enzymes. The flavin-dependent monooxygenase ChaZ catalyses a Baeyer-Villiger oxidation on resomycin C to form a seven-membered lactone. Subsequently, a ketoreductase ChaE rearranges the carbon skeleton and affords the alpha-pyrone containing pentacyclic intermediate in an NADPH-dependent manner via tandem reactions including the reduction of the lactone carbonyl group, Aldol-type reaction, followed by a spontaneous gamma-lactone ring formation, oxidation and aromatization. Our work reveals an unprecedented function of a ketoreductase that contributes to generate structural complexity of aromatic polyketide.

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