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学科主题: 生命有机化学
题名: Radical-mediated enzymatic carbon chain fragmentation-recombination
其他题名: Radical-mediated enzymatic carbon chain fragmentation-recombination
作者: ZHANG QI ; Li YX(李玉学) ; CHEN DANDAN ; YU YI ; DUAN LIAN ; SHEN BEN ; Liu W(刘文)
通讯作者: 刘文
刊名: Nat. Chem. Biol.
发表日期: 2011-01-01
卷: 7, 期:3, 页:154-160
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 美国威斯康星大学
英文摘要: The radical S-adenosylmethionine (S-AdoMet) superfamily contains thousands of proteins that catalyze highly diverse conversions, most of which are poorly understood, owing to a lack of information regarding chemical products and radical-dependent transformations. We here report that NosL, involved in forming the indole side ring of the thiopeptide nosiheptide (NOS), is a radical S-AdoMet 3-methyl-2-indolic acid (MIA) synthase. NosL catalyzed an unprecedented carbon chain reconstitution of L-tryptophan to give MIA, showing removal of the C alpha-N unit and shift of the carboxylate to the indole ring. Dissection of the enzymatic process upon the identification of products and a putative glycyl intermediate uncovered a radical-mediated, unusual fragmentation-recombination reaction. This finding unveiled a key step in radical S-AdoMet enzyme-catalyzed structural rearrangements during complex biotransformations. Additionally, NosL tolerated fluorinated L-tryptophan as the substrate, allowing for production of a regiospecifically halogenated thiopeptide that has not been found among the more than 80 members of the naturally occurring thiopeptide family.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000287307600008
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28471
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:
ZHANG QI,Li YX,CHEN DANDAN,et al. Radical-mediated enzymatic carbon chain fragmentation-recombination[J]. Nat. Chem. Biol.,2011,7(3):154-160.
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