Knowledge Management System of Northwest Institute of Plateau Biology, CAS
Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase | |
Wang, Jinhu ; Hou, Qianqian ; Sheng, Xiang ; Gao, Jun ; Liu, Yongjun ; Liu, Chengbu ; 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
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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. |
文献类型 | 期刊论文 |
条目标识符 | http://210.75.249.4/handle/363003/47282 |
专题 | 中国科学院西北高原生物研究所 |
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, Wang, JH; Hou, QQ; Sheng, X; Gao, J; Liu, YJ; Liu, CB.Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase,INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2013,113(8):1071-1075,2013. |
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. |
MLA | Wang, Jinhu,et al."Theoretical study on the deglycosylation mechanism of rice BGlu1 beta-glucosidase".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2013). |
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