Highly stereoselective α-glycosylation with GalN3 donors enabled collective synthesis of mucin-related tumor associated carbohydrate antigens

doi:10.1039/d4sc01348d

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	Highly stereoselective α-glycosylation with GalN3 donors enabled collective synthesis of mucin-related tumor associated carbohydrate antigens
	Shou, Kunxiu; Zhang, Yunqin; Ji, Yujie; Liu, Bin; Zhou, Qingli; Tan, Qiang; Li, Fuying; Wang, Xiufang; Lu, Gang; Xiao, Guozhi
	2024
发表期刊	CHEMICAL SCIENCE
ISSN	2041-6520
卷号	15 期号:17 页码:6552-6561
摘要	Mucin-related tumor-associated carbohydrate antigens (TACAs) are important and interesting targets for cancer vaccine therapy. However, efficient access to a library of mucin-related TACAs remains a challenging task. One of the key issues is the challenging construction of alpha-GalNAc linkages. Here, we report highly stereoselective alpha-glycosylation with GalN(3) N-phenyl trifluoroacetimidate donors, which features excellent yields, outstanding stereoselectivities, broad substrate scope and mild reaction conditions. This method is successfully applied to highly stereoselective synthesis of GalN(3)-alpha-O-Ser, which served as the common intermediate for collective synthesis of a wide range of TACAs including T-N antigen, STN antigen, 2,6 STF antigen, 2,3 STF antigen, glycophorin and cores 1-8 mucin-type O-glycans. In particular, the rationale for this highly stereoselective alpha-glycosylation is provided for the first time using DFT calculations and mechanistic studies, highlighting the crucial roles of reagent combinations (TMSI and Ph3PO) and the H-bonding directing effect of the N-3 group.
DOI	10.1039/d4sc01348d
WOS记录号	WOS:001198155800001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75972
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Shou, Kunxiu,Zhang, Yunqin,Ji, Yujie,et al. Highly stereoselective α-glycosylation with GalN3 donors enabled collective synthesis of mucin-related tumor associated carbohydrate antigens[J]. CHEMICAL SCIENCE,2024,15(17):6552-6561.
APA	Shou, Kunxiu.,Zhang, Yunqin.,Ji, Yujie.,Liu, Bin.,Zhou, Qingli.,...&Xiao, Guozhi.(2024).Highly stereoselective α-glycosylation with GalN3 donors enabled collective synthesis of mucin-related tumor associated carbohydrate antigens.CHEMICAL SCIENCE,15(17),6552-6561.
MLA	Shou, Kunxiu,et al."Highly stereoselective α-glycosylation with GalN3 donors enabled collective synthesis of mucin-related tumor associated carbohydrate antigens".CHEMICAL SCIENCE 15.17(2024):6552-6561.

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