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

Zahid H. Soomro, Samy Cecioni, Helen Blanchard, Jean-Pierre Praly, Anne Imberty, Sébastien Vidal, Susan E. Matthews

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)6587-6597
Number of pages11
JournalOrganic & Biomolecular Chemistry
Volume9
Issue number19
DOIs
Publication statusPublished - 2011

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