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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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Publication details

The article was received on 08 Jan 2008, accepted on 11 Feb 2008 and first published on 29 Feb 2008


Article type: Paper
DOI: 10.1039/B800283E
Citation: Org. Biomol. Chem., 2008,6, 1425-1434
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    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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