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CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins

Journal Article


Abstract


  • 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 resorcin[4]arene core. The development of diastereoselective synthetic routes for the formation of lower-rim propargylated resorcin[4]arenes 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. © 2011 The Royal Society of Chemistry.

Publication Date


  • 2011

Citation


  • Soomro, Z. H., Cecioni, S., Blanchard, H., Praly, J. P., Imberty, A., Vidal, S., & Matthews, S. E. (2011). CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins. Organic and Biomolecular Chemistry, 9(19), 6587-6597. doi:10.1039/c1ob05676j

Scopus Eid


  • 2-s2.0-80052743133

Start Page


  • 6587

End Page


  • 6597

Volume


  • 9

Issue


  • 19

Abstract


  • 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 resorcin[4]arene core. The development of diastereoselective synthetic routes for the formation of lower-rim propargylated resorcin[4]arenes 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. © 2011 The Royal Society of Chemistry.

Publication Date


  • 2011

Citation


  • Soomro, Z. H., Cecioni, S., Blanchard, H., Praly, J. P., Imberty, A., Vidal, S., & Matthews, S. E. (2011). CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins. Organic and Biomolecular Chemistry, 9(19), 6587-6597. doi:10.1039/c1ob05676j

Scopus Eid


  • 2-s2.0-80052743133

Start Page


  • 6587

End Page


  • 6597

Volume


  • 9

Issue


  • 19