Glycerol and glycerol glycol glycodendrimers

Non-covalent interactions between structural parts of complex oligosaccharides and saccharide-recognising proteins are of crucial importance for many cell communication phenomena. Specificity of such interactions and stability of these ligand-receptor complexes are achieved through multivalent interactions between multiple copies of a saccharide ligand and a corresponding number of protein receptors. Substances presenting multiple copies of the saccharide ligand on easily accessible scaffold molecules therefore appear to be promising tools for study of multivalent interactions and their possible inhibition. Such multivalent glycomimetics can be prepared by attachment of saccharide residues to the surface functional groups of dendrimers. In the course of our work, we have prepared novel glycodendrimers with glycerol and glycerol glycol polyether scaffolds. Isopropylidene-protected hydroxyethyl mannoside was chosen as the carbohydrate component, with the construction of the dendritic structures proceeding by a convergent approach featuring iterative Williamson etherification and ozonolysis/hydride reduction steps. Deprotected representatives of such structures are potential inhibitors of mannose-binding lectins of E. coli. Three representative compounds were deprotected and their anti-adhesive properties were examined. The route to these glycodendrimers was also evaluated in terms of synthetic chemistry. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).