Synthesis of glycocluster-containing conjugates for a vaccine against cholera

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 aci...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-04, Vol.17 (16), p.449-46
Main Authors: Pfister, Hélène B, Kelly, Meagan, Qadri, Firdausi, Ryan, Edward T, Ková, Pavol
Format: Article
Language:English
Subjects:
Alkynes
Antigens
Bacteria
Carbohydrate Conformation
Carbohydrates
Chemical synthesis
Cholera
Cholera - immunology
Clusters
Conjugates
Cycloaddition
Humans
Immunoreactivity
Infections
O Antigens - chemistry
O Antigens - immunology
Oligosaccharides
Organic chemistry
Pathogens
Polysaccharides
Public health
Vaccines
Vaccines - immunology
Vibrio cholerae O1 - chemistry
Vibrio cholerae O1 - immunology
Waterborne diseases
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Summary: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. The glycocluster-containing conjugates for a vaccine against cholera showed immunoreactivity comparable to conventional conjugates.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00368a