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Glycodendrimers as chondroitin sulfate mimetics: synthesis and binding to growth factor midkine

IIQ

P. Domínguez-Rodríguez, J.J. Reina, S. Gil-Caballero, P.M. Nieto, J.L. de Paz, J. Rojo Chemistry: A European Journal 2017, Vol. 23, 11338-11345

Chondroitin sulfate (CS) is a member of the glycosaminoglycan (GAG) family, a class of polysaccharides implicated in relevant biological functions. The structural complexity of these carbohydrates demands the development of simple glycomimetics as useful tools to study the biological processes where GAGs are involved. In this work we described the synthesis of the disaccharide unit of the CS-E (GlcA-GalNAc(4,6-di-OSO3)), in a multivalent presentation. Using a fluorescence polarization competition assay we have demonstrated that a hexavalent dendrimer of this disaccharide interact with midkine, in the low micromolar range. This result highlights the potency of these disaccharide-displaying multivalent systems as interesting mimetics of longer and synthetically more complex GAG oligosaccharides.