Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase

doi:10.1002/qua.24131

NWIPB OpenIR

	Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase
	Wang, Jinhu 1; Hou, Qianqian 1; Sheng, Xiang 1; Gao, Jun 1; Liu, Yongjun 1,2; Liu, Chengbu 1; Wang, JH (reprint author), Shandong Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Colloid & Interface Chem, Jinan 250100, Shandong, Peoples R China.
	2013-04-15
发表期刊	INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
ISSN	0020-7608
卷号	113 期号:8 页码:1071-1075
文章类型	Article
摘要	It is proposed that the catalysis of GH1 enzymes follows a double-displacement mechanism involving a glycosylation and a deglycosylation steps. In this article, the deglycosylation step was studied using quantum mechanical/molecular mechanical (QM/MM) approach. The calculation results reveal that the nucleophilic water (Wat1) attacks to the anomeric C1, and the deglycosylation step experiences a barrier of 21.4 kcal/mol from the glycosyl-enzyme intermediate to the hydrolysis product, in which an oxocarbenium cation-like transition state (TS) is formed. At the TS, the covalent glycosyl-enzyme bond is almost broken (distance of 2.45 angstrom), and the new covalent bond between the attacking oxygen of the water molecule and C1 is basically established (length of 2.14 angstrom). In addition, a short hydrogen bridge is observed between the nucleophilic E386 and the C2OH of sugar ring (distance of 1.94 angstrom) at the TS, which facilitates the ring changing from a chair form to half-chair form, and stabilizes the oxocarbenium cation-like TS. (c) 2013 Wiley Periodicals, Inc.; It is proposed that the catalysis of GH1 enzymes follows a double-displacement mechanism involving a glycosylation and a deglycosylation steps. In this article, the deglycosylation step was studied using quantum mechanical/molecular mechanical (QM/MM) approach. The calculation results reveal that the nucleophilic water (Wat1) attacks to the anomeric C1, and the deglycosylation step experiences a barrier of 21.4 kcal/mol from the glycosyl-enzyme intermediate to the hydrolysis product, in which an oxocarbenium cation-like transition state (TS) is formed. At the TS, the covalent glycosyl-enzyme bond is almost broken (distance of 2.45 angstrom), and the new covalent bond between the attacking oxygen of the water molecule and C1 is basically established (length of 2.14 angstrom). In addition, a short hydrogen bridge is observed between the nucleophilic E386 and the C2OH of sugar ring (distance of 1.94 angstrom) at the TS, which facilitates the ring changing from a chair form to half-chair form, and stabilizes the oxocarbenium cation-like TS. (c) 2013 Wiley Periodicals, Inc.
关键词	Qm Mm Deglycosylation -glucosidases Laminaribiose Reaction Mechanism
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1002/qua.24131
关键词[WOS]	CRYSTAL-STRUCTURE ; MOLECULAR-DYNAMICS ; SUBSTRATE-SPECIFICITY ; AGLYCONE SPECIFICITY ; CATALYTIC MECHANISM ; ZEOLITE STRUCTURE ; QM/MM ; GLYCOSIDASE ; INSIGHTS ; MAIZE
收录类别	SCI
语种	英语
项目资助者	Natural Science Foundation of China(21173129)
WOS研究方向	Chemistry ; Mathematics ; Physics
WOS类目	Chemistry, Physical ; Mathematics, Interdisciplinary Applications ; Physics, Atomic, Molecular & Chemical
WOS记录号	WOS:000315957500003
引用统计	被引频次：6[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://210.75.249.4/handle/363003/3949
专题	中国科学院西北高原生物研究所
通讯作者	Wang, JH (reprint author), Shandong Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Colloid & Interface Chem, Jinan 250100, Shandong, Peoples R China.
作者单位	1.Shandong Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Colloid & Interface Chem, Jinan 250100, Shandong, Peoples R China 2.Chinese Acad Sci, Northwest Inst Plateau Biol, Xining 810001, Qinghai, Peoples R China
推荐引用方式 GB/T 7714	Wang, Jinhu,Hou, Qianqian,Sheng, Xiang,et al. Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2013,113(8):1071-1075.
APA	Wang, Jinhu.,Hou, Qianqian.,Sheng, Xiang.,Gao, Jun.,Liu, Yongjun.,...&Wang, JH .(2013).Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase.INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,113(8),1071-1075.
MLA	Wang, Jinhu,et al."Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 113.8(2013):1071-1075.

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