Chemoenzymatic synthesis of GM3 and GM2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis and solid phase applications

被引：24

作者：

Jacques, S ^{[1
]}

Rich, JR ^{[1
]}

Ling, CC ^{[1
]}

Bundle, DR ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Alberta Ingenu Ctr Carbohydrate Sci, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 01期

关键词：

D O I：

10.1039/b513595h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Analogues of GM(3) and GM(2) gangliosides were chemoenzymatically synthesized on a multifunctional ceramide- type tether designed to facilitate diverse strategies for glycoconjugate synthesis. The truncated ceramide aglycon maintains the stereogenic centres of natural ceramide while avoiding extensive hydrophobicity that can hamper synthesis and purification of the glycolipids. Tetanus toxoid and BSA glycoconjugates of these two gangliosides were prepared for immunization of mice, and for solid phase assays to screen for ganglioside-specific antibodies. Inhibition experiments showed that antibodies generated by tetanus toxoid conjugates of GM(3) and GM(2) exhibited specificity for the carbohydrate epitope and the stereogenic centres of the ceramide.

引用

页码：142 / 154

页数：13

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