Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 32, Pages 9056-9067Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700787
Keywords
bacterial adhesion carbohydrates; dendrimers; mannosylation
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Dendrimer chemistry is an attractive concept for mimicry of the highly branched character of the bioactive carbohydrates found as part of a cell's sugar coat, called the glycocalyx. Glycodendrimers have thus been used to study biological processes occurring on cell surfaces, such as bacterial adhesion. This paper details a new approach in glycodendrimer synthesis, in which a 3,6-diallylated carbohydrate is utilised as core molecule, hydroboration-oxidation is the activating step, and glycosylation with branched and unbranched sugar trichloroacetimidates is used for dendritic growth. To obtain pure dendritic pseudo-tri- and -heptasaccharides in good yields, radical addition of mercaptoethanol to peripheral double bonds was also evaluated with great success. A collection of six new hyper-branched glycodendrons was tested for their potential as inhibitors of type 1 fimbriae-mediated bacterial adhesion in an ELISA and the results were interpreted with regard to sugar valency and spacer characteristics.
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