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

doi:10.1039/d0qo00363h

	Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate
	Xu, Ke 2; Man, Qingmin 3,4; Zhang, Yang 2; Guo, Jia 2; Liu, Yichu 2,4; Fu, Zunyun 1,4; Zhu, Yueyue 2; Li, Yingxia 2; Zheng, Mingyue 4; Ding, Ning 2,5
刊名	ORGANIC CHEMISTRY FRONTIERS
	2020-07-07
卷号	7 期号:13 页码:1606-1615
ISSN号	2052-4129
DOI	10.1039/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.
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关键词	PROTECTING GROUP ; CHEMICAL GLYCOSYLATION ; O-GLYCOSYLATION ; DONORS ; STEREOSELECTIVITY ; MECHANISM ; PHOSPHITE ; CATIONS
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000544472100003
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/291880]
专题	中国科学院上海药物研究所
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.