CuAAC synthesis of resorcinarene-based glycoclusters as multivalent ligands of lectins
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Synthetic multivalent glycoclusters show promise as anti-adhesives for the treatment of bacterial infections. Here we report the synthesis of a family of tetravalent galactose and lactose functionalised macrocycles based on the resorcinarene core. The development of diastereoselective synthetic routes for the formation of lower-rim propargylated resorcinarenes and their functionalistion via Cu-catalyzed azide-alkyne click chemistry is described. ELLA binding studies confirm that galactose sugar clusters are effective ligands for the PA-IL bacterial lectin of Pseudomonas aeruginosa while poor binding for the lactose-based monovalent probe and no binding could be measured for the multivalent glycoclusters was observed for the human galectin-1.
Organic & Biomolecular Chemistry
Biologically Active Molecules