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

Soomro, Zahid H., Cecioni, Samy, Blanchard, Helen, Praly, Jean-Pierre, Imberty, Anne, Vidal, Sébastien and Matthews, Susan E. ORCID: (2011) CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins. Organic & Biomolecular Chemistry, 9 (19). pp. 6587-6597. ISSN 1477-0520

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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 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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User: Users 2731 not found.
Date Deposited: 12 Oct 2011 10:16
Last Modified: 03 May 2024 00:08
DOI: 10.1039/C1OB05676J

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