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Mechanism of the Humicola insolens Cel7B E197S mutant catalyzed flavonoid glycosides synthesis: a QM/MM metadynamics simulation study
Zhang, Yu; Yan, Shihai; Yao, Lishan
2013-06-01
发表期刊THEORETICAL CHEMISTRY ACCOUNTS
卷号132期号:6页码:1-10
摘要 The reaction path of Humicola insolens Cel7B E197S catalyzed glycosylation of luteolin by a-lactosyl fluoride was investigated using QM/MM metadynamics simulations. The catalysis proceeds via a sequential mechanism. Firstly, a proton transfers from the glycosyl acceptor, luteolin, to the catalytic acid/base residue, E202. Secondly, the C1–F covalent bond of the glycosyl donor, a-lactosyl fluoride, is cleaved with the assistance of the hydroxyl group of S197, and the F anion captures the
carboxylic proton of D199, while the conformation of the glycosyl ring at -1 subsite changes from a chair to a halfchair. Thirdly, a new glycosidic bond is formed between C1 of the lactosyl cation and O4
0 of the luteolin anion during which a 1,4B boat conformation comes into being for the subsite -1 glycosyl ring. The rate-limiting step is the C1–F bond cleavage with a barrier of *25.9 kcal/mol. The
change of geometric parameters and hydrogen bonds in the active site along the reaction is analyzed, revealing the important role of residues S197, D199, and E202.
; The reaction path of Humicola insolens Cel7B E197S catalyzed glycosylation of luteolin by alpha-lactosyl fluoride was investigated using QM/MM metadynamics simulations. The catalysis proceeds via a sequential mechanism. Firstly, a proton transfers from the glycosyl acceptor, luteolin, to the catalytic acid/base residue, E202. Secondly, the C-1-F covalent bond of the glycosyl donor, a-lactosyl fluoride, is cleaved with the assistance of the hydroxyl group of S197, and the F anion captures the carboxylic proton of D199, while the conformation of the glycosyl ring at -1 subsite changes from a chair to a half-chair. Thirdly, a new glycosidic bond is formed between C-1 of the lactosyl cation and O-4(') of the luteolin anion during which a (1,4) B boat conformation comes into being for the subsite -1 glycosyl ring. The rate-limiting step is the C1-F bond cleavage with a barrier of similar to 25.9 kcal/mol. The change of geometric parameters and hydrogen bonds in the active site along the reaction is analyzed, revealing the important role of residues S197, D199, and E202.
文章类型Article
关键词Glycosynthase Catalytic Mechanism Free Energy Surface Qm/mm Metadynamics Molecular Dynamics
学科领域仿真与模拟
WOS标题词Science & Technology ; Physical Sciences
DOI10.1007/s00214-013-1367-3
关键词[WOS]AB-INITIO METADYNAMICS ; MOLECULAR-DYNAMICS ; OLIGOSACCHARIDE SYNTHESIS ; CRYSTAL-STRUCTURE ; FORCE-FIELD ; GLYCOSYNTHASES ; ENZYMES ; INTEGRATION ; HYDROLYSIS
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Physical
WOS记录号WOS:000320448400006
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文献类型期刊论文
条目标识符http://ir.qibebt.ac.cn/handle/337004/1641
专题蛋白质设计研究组
作者单位Chinese Acad Sci, Key Lab Biofuels, Qingdao Inst Bioenergy & Bioproc, Qingdao 266061, Peoples R China
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Zhang, Yu,Yan, Shihai,Yao, Lishan. Mechanism of the Humicola insolens Cel7B E197S mutant catalyzed flavonoid glycosides synthesis: a QM/MM metadynamics simulation study[J]. THEORETICAL CHEMISTRY ACCOUNTS,2013,132(6):1-10.
APA Zhang, Yu,Yan, Shihai,&Yao, Lishan.(2013).Mechanism of the Humicola insolens Cel7B E197S mutant catalyzed flavonoid glycosides synthesis: a QM/MM metadynamics simulation study.THEORETICAL CHEMISTRY ACCOUNTS,132(6),1-10.
MLA Zhang, Yu,et al."Mechanism of the Humicola insolens Cel7B E197S mutant catalyzed flavonoid glycosides synthesis: a QM/MM metadynamics simulation study".THEORETICAL CHEMISTRY ACCOUNTS 132.6(2013):1-10.
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