Functionalization of oligosaccharide mimetics and multimerization using squaric diester-mediated coupling

Functionalized carbohydrate-centered glycoclusters formed the starting material for the synthesis of tagged oligosaccharide and glycoconjugate mimetics, which were obtained by thiourea-bridging, peptide coupling and in particular squaric diester-mediated coupling. The latter method could also be utilized to provide new multivalent glycoconjugates, which were tested for their anti-adhesive properties in an ELISA with Escherichia coli bacteria.

Carbohydrate-centered glycoclusters were fluorescence-labeled, functionalized to amphiphilic conjugates and multimerized using squaric acid. Inhibitory potencies in bacterial adhesion were measured.Figure optionsDownload as PowerPoint slide