Conjugation of oligosaccharides to chondroitin oligomer and γ-cyclodextrin

Carbohydrate epitopes on cell surfaces are involved in various biological processes including cell–cell interactions, cell differentiation, cancer metastasis, and pathogen invasion. By blocking clinically relevant sugar receptors, synthetic carbohydrates have potential to become specific pharmaceuticals in various diseases. To achieve the necessary avidity, multivalent glycoconjugates have been constructed thus mimicking multivalent binding often adopted by cells and tissues. Here, we present methodology to create multivalent carbohydrate conjugates based on chondroitin and cyclodextrin carriers. Human milk tetrasaccharide LNnT was attached through a β-glycosylamide linkage to a chondroitin oligomer or an oxidized γ-cyclodextrin. In addition, a facile method was created to attach oligosaccharides to a cyclodextrin carrier using a linker including an oxime-linkage.