A mannosylated pillar[5]arene derivative: Chiral information transfer and antiadhesive properties against uropathogenic bacteria

A pillar[5]arene derivative substituted with 10 peripheral acetylated mannosyl moieties has been prepared by grafting an alkynylated mannose derivative onto the macrocyclic core under the copper-catalyzed alkyne-azide cycloaddition conditions. Deacetylation of the resulting compound provided a pillar[5]arene glycocluster. NMR investigations have shown that the chiral information transfer between the different subunits of this molecule is highly sensitive to both the temperature and the solvent. Finally, the glycoconjugate has been assayed as an inhibitor of the adhesion of an uropathogenic Escherichia coli strain to red blood cells.