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Issue 16, 2019
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Synthesis of glycocluster-containing conjugates for a vaccine against cholera

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Abstract

Glycoclusters displaying synthetic fragments of the O-specific polysaccharide (OSP) of Vibrio cholerae O1 serotype Inaba on a carbohydrate platform were prepared by Cu(I)-catalysed azide alkyne cycloaddition (CuAAC, click chemistry). The clusters were subsequently conjugated to BSA via squaric acid chemistry. Their immunoreactivity was compared with those of similar conventional conjugates, i.e. made from single oligosaccharides presented in non cluster form, using plasma of patients recovering from cholera. The results showed that the conjugates were displayed in immunologically relevant manners and that the immunoreactivity of hexasaccharide–cluster conjugates was similar to that of a conjugate displaying OSP isolated from wild type V. cholerae, further supporting the immunologic relevance of antigens made from synthetic oligosaccharides.

Graphical abstract: Synthesis of glycocluster-containing conjugates for a vaccine against cholera

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Publication details

The article was received on 14 Feb 2019, accepted on 25 Mar 2019 and first published on 01 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00368A
Citation: Org. Biomol. Chem., 2019,17, 4049-4060

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    Synthesis of glycocluster-containing conjugates for a vaccine against cholera

    H. B. Pfister, M. Kelly, F. Qadri, E. T. Ryan and P. Kováč, Org. Biomol. Chem., 2019, 17, 4049
    DOI: 10.1039/C9OB00368A

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