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

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.