A General Chemoenzymatic Strategy for the Synthesis of Glycosphingolipids

被引：14

作者：

Liu, Yunpeng ^{[1
,2
,3
]}

Wen, Liuqing ^{[3
]}

Li, Lei ^{[3
]}

Gadi, Madhusudhan Reddy ^{[3
]}

Guan, Wanyi ^{[3
]}

Huang, Kenneth ^{[3
]}

Xiao, Zhongying ^{[3
]}

Wei, Mohui ^{[3
]}

Ma, Cheng ^{[3
]}

Zhang, Qing ^{[3
]}

Yu, Hai ^{[4
]}

Chen, Xi ^{[4
]}

Wang, Peng George ^{[1
,2
,3
]}

Fang, Junqiang ^{[1
,2
]}

机构：

[1] Shandong Univ, Natl Glycoengn Res Ctr, Shandong Prov Key Lab Carbohydrate Chem, Jinan 250100, Shandong, Peoples R China

[2] Shandong Univ, State Key Lab Microbial Technol, Jinan 250100, Shandong, Peoples R China

[3] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

[4] Univ Calif Davis, Dept Chem, One Shields Ave, Davis, CA 95616 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 25期

基金：

美国国家卫生研究院; 中国博士后科学基金;

关键词：

Enzyme catalysis; Glycosylation; Glycosphingolipids; Medicinal chemistry; D-RIBO-PHYTOSPHINGOSINE; D-ERYTHRO-SPHINGOSINE; EFFICIENT SYNTHESIS; SIALIDASE ACTIVITIES; ENZYMATIC-SYNTHESIS; CONCISE SYNTHESIS; GANGLIOSIDE; SIALYLTRANSFERASE; ANALOGS; OLIGOSACCHARIDES;

D O I：

10.1002/ejoc.201600950

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, prototypical, and stereoselective strategy for the synthesis of therapeutically and immunologically significant glycosphingolipids has been developed. This strategy provides a universal platform for glycosphingolipid synthesis by block coupling of enzymatically prepared free oligosaccharide-glycans to lipids using glycosyl N-phenyltrifluoroacetimidates as efficient activated intermediates. As demonstrated here, two different types of glycosphingolipids were obtained in excellent yields using the method.

引用

页码：4315 / 4320

页数：6

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