The synthesis of multivalent neoglycoconjugates is currently promoted by the extensive findings of multiple ligand-receptor interactions that occur in the nature and by the phenomenon generally referred to as the glycoside cluster effect [1]. In this sense, inhibition of Cholera toxin binding by targeting the CTB-receptor interaction is a particularly attractive approach with therapeutic potential for the treatment of cholera disease.
In the present work, we present the synthesis of a series of water soluble glycoclusters consisting on Boltorn H30 hyperbranched polymers functionalized with the naturally occurring ß-Galceramide (see Figure) and analogs, providing a platform that could mimic the natural GM1-enriched lipid domains. These functionalized dendritic polymers were tested against cholera toxin (CTB5) and other lectins.
1. (a) Lundquist, J.J.; Toone, E.J.Chem. Rev.2002,102, 555−578. (b) Mammen, M.; Choi, S.K.; Whitesides, G.M.Angew. Chem. Int. Ed.1998, 37, 2754−2794.
