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Differential Recognition of Mannose-Based Polysaccharides by Tripodal Receptors Based on a Triethylbenzene Scaffold Substituted with Trihydroxybenzoyl Moieties

AuthorsCarrero, Paula ; Ardá, Ana ; Alvarez, Mónica; Doyagüez, Elisa G.; Rivero-Buceta, Eva ; Quesada, Ernesto ; Prieto, Alicia ; Solís, Dolores; Camarasa Rius, María José ; Peréz-Pérez, María-Jesús ; Jiménez-Barbero, Jesús ; San-Félix, Ana
Conformational analysis
Molecular recognition
Issue Date2013
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry (1) : 65-76 (2013)
AbstractThe tripodal receptors 1 and 2 based on a triethylbenzene scaffold substituted with trihydroxybenzoyl groups have been synthesised. The conformational preferences and carbohydrate-binding ability of 1 and 2 have been examined by NMR spectroscopy and modelling procedures. The results reveal that the particular structural pre-organisation of 2 facilitates the recognition, in a highly competitive medium (DMSO), of a mannose-based polysaccharide consisting of a linear saccharide chain continuously decorated by α(1 2)-linked branching mannose moieties. By contrast, other α(1 2)-substituted polysaccharides or different monosaccharides are not bound, revealing the selectivity of the interaction. Due to the importance of α(1 2) mannosides, which are abundantly present on the glycan shield of several pathogens, the results reported here open attractive prospects for the potential application of 2 or its derivatives in future antiinfective strategies.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.201201239
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