Carbohydration of 1,4,8,11-tetraazacyclotetradecane (cyclam): synthesis and binding properties toward concanavalin A

Two novel glycocluster ligands with cyclam core bearing thiourea-linked d-glucose and 2-acetamido-2-deoxy-d-glucose at the periphery have been synthesized. The interaction with concanavalin A has been studied by isothermal titration microcalorimetry for characterizing protein-ligand interactions. The sugar-containing multivalent ligands showed higher association affinity compared to the sugar monomers, which is attributed to an entropy driven glycoside clustering effect.