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Synthesis of N-modified ganglioside GM3 derivatives
Zheng, Mingwei; Ye, Xin-Shan
关键词N-Modified ganglioside GM3 Carbohydrate Synthesis
刊名TETRAHEDRON
2012-02-04
DOI10.1016/j.tet.2011.12.019
68期:5页:1475-1482
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]GLYCOSYNAPTIC MICRODOMAINS ; EFFICIENT SYNTHESIS ; CELL-GROWTH ; CERAMIDE ; GM(3) ; SPHINGOLIPIDS ; MOTILITY ; ADHESION ; ANALOGS ; MOIETY
英文摘要

Ganglioside GM3 and its derivatives have many important biological functions. Using diethyl phosphite protected sialic acid as glycosyl donor and 3,2′,3′,4′-unprotected lactose as glycosyl acceptor, the sialic acid-containing trisaccharide was assembled with excellent anomeric stereoselectivity. The trisaccharide was further coupled with ceramide precursor to yield sphingosine 1. Based on this key intermediate, two different series of N-modified GM3 analogues with modifications on either the nitrogen of sialic acid residue or the nitrogen of ceramide moiety and GM3 itself were synthesized smoothly. (C) 2011 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000299759000019
项目编号2012CB822100
资助机构National Natural Science Foundation of China ; Ministry of Science and Technology of China
引用统计
被引频次:4[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/65792
专题北京大学药学院
北京大学药学院_药物化学系
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
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GB/T 7714
Zheng, Mingwei,Ye, Xin-Shan. Synthesis of N-modified ganglioside GM3 derivatives[J]. TETRAHEDRON,2012,68(5):1475-1482.
APA Zheng, Mingwei,&Ye, Xin-Shan.(2012).Synthesis of N-modified ganglioside GM3 derivatives.TETRAHEDRON,68(5),1475-1482.
MLA Zheng, Mingwei,et al."Synthesis of N-modified ganglioside GM3 derivatives".TETRAHEDRON 68.5(2012):1475-1482.
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