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学科主题: 生命有机化学
题名: 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
作者: Duan L(段炼) ; Wang SF(王守锋) ; Liao RJ(廖日晶) ; Liu W(刘文)
通讯作者: 刘文
刊名: Chem. Biol.
发表日期: 2012-01-01
卷: 19, 期:4, 页:443-448
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: 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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000303371500006
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28531
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
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.
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