A Self-Assembled Pyrrolic Cage Receptor Specifically Recognizes β-Glucopyranosides

We have described a new synthetic cage receptor, quantitatively obtained by a one-pot reduction of a spontaneously self-assembled macrobicyclic cage, which forms by condensation of five component molecules through the thermodynamically controlled formation of six imine bonds. The receptor specifically recognizes the b anomer of d-glucose and its alkyl glucosides with complete b/a selectivity and effectively discriminates b monosaccharides of the gluco series from both the a and b anomers of the galacto and manno series. The discovery is bound to have an impact on the understanding of the structural features and the rational design of synthetic receptors for the molecular recognition of carbohydrates