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Issue 1, 2006
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Chemoenzymatic synthesis of GM3 and GM2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis and solid phase applications

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Abstract

Analogues of GM3 and GM2 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 GM3 and GM2 exhibited specificity for the carbohydrate epitope and the stereogenic centres of the ceramide.

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

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Publication details

The article was received on 26 Sep 2005, accepted on 27 Oct 2005 and first published on 30 Nov 2005


Article type: Paper
DOI: 10.1039/B513595H
Citation: Org. Biomol. Chem., 2006,4, 142-154
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    Chemoenzymatic synthesis of GM3 and GM2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis and solid phase applications

    S. Jacques, J. R. Rich, C. Ling and D. R. Bundle, Org. Biomol. Chem., 2006, 4, 142
    DOI: 10.1039/B513595H

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