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Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate

文献类型：期刊论文

作者Xu, Ke2; Man, Qingmin3,4; Zhang, Yang2; Guo, Jia2; Liu, Yichu2,4; Fu, Zunyun1,4; Zhu, Yueyue2; Li, Yingxia2; Zheng, Mingyue4; Ding, Ning2,5
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2020-07-07
卷号7期号:13页码:1606-1615
ISSN号2052-4129
DOI10.1039/d0qo00363h
通讯作者Zheng, Mingyue(myzheng@simm.ac.cn) ; Ding, Ning(dingning@fudan.edu.cn)
英文摘要Unlike theO2 neighboring group participation in glycosylation, the participating effect of esters located on more remote positions of glycopyranosyl donors has not been unambiguously established and provokes plenty of questions. Here we systematically trapped the participation intermediates on three common pyranoses based on a 'bis-trichloroacetimidates method', which showed that trichloroacetimidate group participations fromO4 andO6 are all quite possible except ford-mannopyranosylO4. Besides, with the trapped participation intermediates in hand, the NMR data was collected to assist the DFT calculations to build up the most possible participating conformations, which, in turn, predicted the potentials of remote participation by trichloroacetimidates at different positions on the same donor. Finally, the 'tris-trichloroacetimidates method' was employed to support the computational calculations. This work provided a conformational perspective on understanding the potent remote acyl group participation in glycosylation reaction.
WOS关键词PROTECTING GROUP ; CHEMICAL GLYCOSYLATION ; O-GLYCOSYLATION ; DONORS ; STEREOSELECTIVITY ; MECHANISM ; PHOSPHITE ; CATIONS
资助项目National Science and Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006-008] ; Shanghai talent development fund (2017) ; National Natural Science Foundation of China[81773634] ; Personalized Medicines-Molecular Signaturebased Drug Discovery and Development, Strategic Priority Research Program of the Chinese Academy of Sciences[XDA12050201]
WOS研究方向Chemistry
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000544472100003
源URL[http://119.78.100.183/handle/2S10ELR8/291880]  
专题新药研究国家重点实验室
通讯作者Zheng, Mingyue; Ding, Ning
作者单位1.Nanjing Univ Chinese Med, 138 Xianlin Rd, Nanjing 210023, Jiangsu, Peoples R China
2.Fudan Univ, Sch Pharm, Dept Med Chem, 826 Zhangheng Rd, Shanghai 201203, Peoples R China
3.Univ Sci & Technol China, 94 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chongzhi Rd, Shanghai 201203, Peoples R China
5.Fudan Univ, Zhangjiang Technol Inst, 825 Zhangheng Rd, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Xu, Ke,Man, Qingmin,Zhang, Yang,et al. Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate[J]. ORGANIC CHEMISTRY FRONTIERS,2020,7(13):1606-1615.
APA Xu, Ke.,Man, Qingmin.,Zhang, Yang.,Guo, Jia.,Liu, Yichu.,...&Ding, Ning.(2020).Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate.ORGANIC CHEMISTRY FRONTIERS,7(13),1606-1615.
MLA Xu, Ke,et al."Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate".ORGANIC CHEMISTRY FRONTIERS 7.13(2020):1606-1615.

入库方式： OAI收割

来源：上海药物研究所

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