Hyperbranched polymers represent an important part of the family of dendritic and multibranched polymers, whose properties are indeed strongly determined by the nature of their terminal groups. The incorporation of glycolipid moieties to these scaffolds creates a new family of glycolipid-based hyperbranched structures. Indeed, the intrinsic microheterogenicity of these hyperbranched dendritic polymers would potentially mimic microdomain formation in lipid membranes which is typically associated with important cellular events such as signaling, vesicle fusion, and pathogen invasion among others. In this context we have developed new methods of enantioselective synthesis of sphingosines and ceramides modified at the fatty acid chain with terminal N3 groups. Dendritic hyperbranched structures based on Boltorn� H30  to which b-GalCer-N3 and other lipidic units were attached, were prepared by using Cu(I)-catalyzed [3+2] alkyne-azide cycloaddition. The inhibition study of these multivalent systems against the cholera toxin will be presented.

Multivalent systems containing glycolipids: Synthesis and biological applications

244th National Meeting (2012)

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