Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies

doi:10.1039/d2sc02176e

KIB OpenIR

	Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies
	Zhang, Yunqin; Hu, Yanlei; Liu, Shanshan; He, Haiqing; Sun, Roujing; Lu, Gang; Xiao, Guozhi
	2022
发表期刊	CHEMICAL SCIENCE
卷号	13 期号:26 页码:7755-7764
摘要	The accessibility to long, branched and complex glycans containing many 1,2-cis glycosidic linkages with precise structures remains a challenging task in chemical synthesis. Reported here is an efficient, stereoselective and orthogonal one-pot synthesis of a tetradecasaccharide and shorter sequences from Lentinus giganteus polysaccharides with antitumor activities. The synthetic strategy consists of: (1) newly developed merging reagent modulation and remote anchimeric assistance (RMRAA) alpha-(1 -> 6)-galactosylation in a highly stereoselective manner, (2) DMF-modulated stereoselective alpha-(1 -> 3)-glucosylation, (3) RMRAA stereoselective alpha-(1 -> 6)-glucosylation, (4) several orthogonal one-pot glycosylations on the basis of N-phenyltrifluoroacetimidate (PTFAI) glycosylation, Yu glycosylation and ortho-(1-phenylvinyl)benzoate (PVB) glycosylation to streamline oligosaccharide synthesis, and (5) convergent [7 + 7] glycosylation for the final assembly of the target tetradecasaccharide. In particular, this new RMRAA alpha-galactosylation method has mild reaction conditions, broad substrate scopes and significantly shortened step counts for the heptasaccharide synthesis in comparison with 4,6-di-tert-butylsilyene (DTBS) directed alpha-galactosylation. Furthermore, DFT calculations shed light on the origins of remote anchimeric assistance effects (3,4-OBz > 3,4-OAc > 4-OBz > 3-OBz) of acyl groups.
关键词	1,2-CIS O-GLYCOSYLATION SELECTIVE SYNTHESIS CHEMICAL-SYNTHESIS OLIGOSACCHARIDE GALACTOSYLATION POLYSACCHARIDE ALKYNYLBENZOATES CONJUGATION ANTIBODIES CATALYSIS
DOI	10.1039/d2sc02176e
收录类别	SCI
WOS记录号	WOS:000806467100001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74653
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Zhang, Yunqin,Hu, Yanlei,Liu, Shanshan,et al. Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies[J]. CHEMICAL SCIENCE,2022,13(26):7755-7764.
APA	Zhang, Yunqin.,Hu, Yanlei.,Liu, Shanshan.,He, Haiqing.,Sun, Roujing.,...&Xiao, Guozhi.(2022).Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies.CHEMICAL SCIENCE,13(26),7755-7764.
MLA	Zhang, Yunqin,et al."Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies".CHEMICAL SCIENCE 13.26(2022):7755-7764.

条目包含的文件		下载所有文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
10.1039_d2sc02176e.p（2403KB）	期刊论文	出版稿	开放获取	CC BY-NC-SA	浏览下载