Radical-mediated enzymatic carbon chain fragmentation-recombination

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	Radical-mediated enzymatic carbon chain fragmentation-recombination
	ZHANG QI ; Li YX(李玉学) ; CHEN DANDAN ; YU YI ; DUAN LIAN ; SHEN BEN ; Liu W(刘文)
刊名	Nat. Chem. Biol.
	2011
卷号	7 期号:3 页码:154-160
ISSN号	1552-4450
其他题名	Radical-mediated enzymatic carbon chain fragmentation-recombination
通讯作者	刘文
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.
学科主题	生命有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1038/NCHEMBIO.512
语种	英语
WOS记录号	WOS:000287307600008
公开日期	2013-08-23
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/28471]
专题	上海有机化学研究所_生命有机化学国家重点实验室
推荐引用方式 GB/T 7714	ZHANG QI,Li YX,CHEN DANDAN,et al. Radical-mediated enzymatic carbon chain fragmentation-recombination[J]. Nat. Chem. Biol.,2011,7(3):154-160.
APA	ZHANG QI.,李玉学.,CHEN DANDAN.,YU YI.,DUAN LIAN.,...&刘文.(2011).Radical-mediated enzymatic carbon chain fragmentation-recombination.Nat. Chem. Biol.,7(3),154-160.
MLA	ZHANG QI,et al."Radical-mediated enzymatic carbon chain fragmentation-recombination".Nat. Chem. Biol. 7.3(2011):154-160.