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: https://orcid.org/0000-0001-8821-0851 (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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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.

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:	23 Oct 2022 01:04
URI:	https://ueaeprints.uea.ac.uk/id/eprint/34991
DOI:	10.1039/C1OB05676J

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