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Insights into Quinaldic Acid Moiety Formation in Thiostrepton Biosynthesis Facilitating Fluorinated Thiopeptide Generation
其他题名硫链丝菌素生物合成过程中喹哪啶酸结构单元合成机制的阐明促进了氟代硫链丝菌素的产生
Duan L(段炼); Wang SF(王守锋); Liao RJ(廖日晶); Liu W(刘文)
2012
发表期刊Chem. Biol.
ISSN1074-5521
卷号19期号:4页码:443-448
摘要Thiostrepton (TSR), often referred as to a parent compound in the thiopeptide family, is a bimacrocyclic member that features a quinaldic acid (QA) moiety-containing side ring appended to the characteristic core system. QA biosynthesis requires an unusual ring-expanding conversion, showing a methyl transfer onto and a rearrangement of the indole part of L-tryptophan to give a quinoline ketone. Herein, we report that the process involves the activities of the radical methyltransferase TsrT, aminotransferase TsrA, dehydrogenase TsrE, and cyclase TsrD. TsrU, a stereospecific oxidoreductase, catalyzes the further conversion of the ketone into an enantiomerically pure S-alcohol. Elucidation of this chemistry, which is common in the biosynthesis of a number of thiopeptides sharing a QA side ring system, facilitates analog generation, as shown by the achievement of region-specific fluorination of thiostrepton with the improved antibacterial activity.
学科领域生命有机化学
部门归属中科院上海有机化学研究所
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收录类别SCI
语种英语
WOS记录号WOS:000303371500006
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被引频次:29[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28531
专题生命有机化学国家重点实验室
通讯作者Liu W(刘文)
推荐引用方式
GB/T 7714
Duan L,Wang SF,Liao RJ,et al. Insights into Quinaldic Acid Moiety Formation in Thiostrepton Biosynthesis Facilitating Fluorinated Thiopeptide Generation[J]. Chem. Biol.,2012,19(4):443-448.
APA 段炼,王守锋,廖日晶,&刘文.(2012).Insights into Quinaldic Acid Moiety Formation in Thiostrepton Biosynthesis Facilitating Fluorinated Thiopeptide Generation.Chem. Biol.,19(4),443-448.
MLA 段炼,et al."Insights into Quinaldic Acid Moiety Formation in Thiostrepton Biosynthesis Facilitating Fluorinated Thiopeptide Generation".Chem. Biol. 19.4(2012):443-448.
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