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- Title
Differential Recognition of Mannose-Based Polysaccharides by Tripodal Receptors Based on a Triethylbenzene Scaffold Substituted with Trihydroxybenzoyl Moieties.
- Authors
Carrero, Paula; Ardá, Ana; Alvarez, Mónica; Doyagüez, Elisa G.; Rivero‐Buceta, Eva; Quesada, Ernesto; Prieto, Alicia; Solís, Dolores; Camarasa, María José; Peréz‐Pérez, María Jesús; Jiménez‐Barbero, Jesús; San‐Félix, Ana
- Abstract
The 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.
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 1, p65
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201201239