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Molecular Basis for the Final Oxidative Rearrangement Steps in Chartreusin Biosynthesis

文献类型： 外文期刊

作者： Wang, Yi Shuang 1 ; Zhang, Bo 1 ; Zhu, Jiapeng 2 ; Yang, Cheng Long 1 ; Guo, Yu 3 ; Liu, Cheng Li 1 ; Liu, Fang 5 ; Huang 1 ;

作者机构： 1.Nanjing Univ, Inst Funct Biomol, Sch Life Sci, State Key Lab Pharmaceut Biotechnol, Nanjing 210023, Jiangsu, Peoples R China

2.Nanjing Univ Chinese Med, Sch Med & Life Sci, State Key Lab Cultivat Base TCM Qual & Efficacy, Nanjing 210023, Jiangsu, Peoples R China

3.Shanghai Tech Univ, iHuman Inst, Shanghai 201210, Peoples R China

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

5.Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, State Key Lab Coordinat Chem, Nanjing 210023, Jiangsu, Peoples R China

期刊名称：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY （ 影响因子：15.419； 五年影响因子：15.801 ）

ISSN： 0002-7863

年卷期： 2018 年 140 卷 34 期

页码：

收录情况： SCI

摘要： Oxidative rearrangements play key roles in introducing structural complexity and biological activities of natural products biosynthesized by type II polyketide synthases (PKSs). Chartreusin (1) is a potent antitumor polyketide that contains a unique rearranged pentacyclic aromatic bilactone aglycone derived from a type II PKS. Herein, we report an unprecedented dioxygenase, ChaP, that catalyzes the final a-pyrone ring formation in 1 biosynthesis using flavin-activated oxygen as an oxidant. The X-ray crystal structures of ChaP and two homologues, docking studies, and site-directed mutagenesis provided insights into the molecular basis of the oxidative rearrangement that involves two successive C-C bond cleavage steps followed by lactonization. ChaP is the first example of a dioxygenase that requires a flavin-activated oxygen as a substrate despite lacking flavin binding sites, and represents a new class in the vicinal oxygen chelate enzyme superfamily.

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