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.
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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. |
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