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Issue 8, 2008
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Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and ‘click’ conjugation

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Abstract

A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using ‘click’ chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.

Graphical abstract: Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and ‘click’ conjugation

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Article information


Submitted
08 Jan 2008
Accepted
11 Feb 2008
First published
29 Feb 2008

Org. Biomol. Chem., 2008,6, 1425-1434
Article type
Paper

Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and ‘click’ conjugation

H. M. Branderhorst, R. Kooij, A. Salminen, L. H. Jongeneel, C. J. Arnusch, R. M. J. Liskamp, J. Finne and R. J. Pieters, Org. Biomol. Chem., 2008, 6, 1425
DOI: 10.1039/B800283E

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