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

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Title CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins
Author Soomro, Zahid H.; Cecioni, Samy; Blanchard, Helen; Praly, Jean-Pierre; Imberty, Anne; Vidal, Sebastien; Matthews, Susan E.
Journal Name Organic and Biomolecular Chemistry
Year Published 2011
Place of publication United Kingdom
Publisher Royal Society of Chemistry
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.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1039/c1ob05676j
Volume 9
Page from 6587
Page to 6597
ISSN 1477-0520
Date Accessioned 2011-11-03; 2012-02-16T05:26:25Z
Research Centre Institute for Glycomics
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Biologically Active Molecules
URI http://hdl.handle.net/10072/42745
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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