Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines
Huang, CS; Yang, CF; Zhang, WJ; Zhang, LP; De, BC; Zhu, YG; Jiang, XD; Fang, CY; Zhang, QB; Yuan, CS; Liu, HW; Zhang, CS; h.w.liu@mail.utexas.edu; czhang2006@gmail.com
2018
发表期刊NATURE COMMUNICATIONS
卷号9页码:-2088
摘要Lomaiviticin A and difluostatin A are benzofluorene-containing aromatic polyketides in the atypical angucycline family. Although these dimeric compounds are potent antitumor agents, how nature constructs their complex structures remains poorly understood. Herein, we report the discovery of a number of fluostatin type dimeric aromatic polyketides with varied C-C and C-N coupling patterns. We also demonstrate that these dimers are not true secondary metabolites, but are instead derived from non-enzymatic deacylation of biosynthetic acyl fluostatins. The non-enzymatic deacylation proceeds via a transient quinone methide like intermediate which facilitates the subsequent C-C/C-N coupled dimerization. Characterization of this unusual property of acyl fluostatins explains how dimerization takes place, and suggests a strategy for the assembly of C-C and C-N coupled aromatic polyketide dimers. Additionally, a deacylase FlsH was identified which may help to prevent accumulation of toxic quinone methides by catalyzing hydrolysis of the acyl group.
部门归属[Huang, Chunshuai; Yang, Chunfang; Zhang, Wenjun; Zhang, Liping; De, Bidhan Chandra; Zhu, Yiguang; Jiang, Xiaodong; Fang, Chunyan; Zhang, Qingbo; Yuan, Cheng-Shan; Zhang, Changsheng] Chinese Acad Sci, South China Sea Inst Oceanol, Key Lab Trop Marine Bioresources & Ecol, RNAM Ctr Marine Microbiol,Guangdong Key Lab Marin, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China; [Huang, Chunshuai; De, Bidhan Chandra; Jiang, Xiaodong; Fang, Chunyan] Univ Chinese Acad Sci, 19 Yuquan Rd, Beijing 100049, Peoples R China; [Liu, Hung-wen] Univ Texas Austin, Coll Pharm, Div Chem Biol & Med Chem, Austin, TX 78712 USA; [Liu, Hung-wen] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
学科领域Science & Technology - Other Topics
资助项目LMB
文献类型期刊论文
条目标识符http://ir.scsio.ac.cn/handle/344004/16945
专题中科院海洋生物资源可持续利用重点实验室
通讯作者h.w.liu@mail.utexas.edu; czhang2006@gmail.com
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Huang, CS,Yang, CF,Zhang, WJ,et al. Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines[J]. NATURE COMMUNICATIONS,2018,9:-2088.
APA Huang, CS.,Yang, CF.,Zhang, WJ.,Zhang, LP.,De, BC.,...&czhang2006@gmail.com.(2018).Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines.NATURE COMMUNICATIONS,9,-2088.
MLA Huang, CS,et al."Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines".NATURE COMMUNICATIONS 9(2018):-2088.
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