A Synthetic Galectin Mimic

Galectins are a galactoside specific subclass of carbohydrate binding proteins (lectins) involved in various cellular activities, certain cancers, infections, inflammations, and many other biological processes. The molecular basis for the selectivity galectins is well-documented revolves around appropriate interaction complementarity: an aromatic residue C−H⋅⋅⋅π interactions polar residues (charge assisted) hydrogen bonds with axial hydroxyl group galactoside. However, no synthetic mimics currently available. We now report on design synthesis first galectin mimic (6), show that it has higher than 65-fold preference n-octyl-β-galactoside (8) over n-octyl-β-glucoside (7) CD2Cl2 containing 5 % [D6]DMSO (with Ka≥4500 M−1 6:8). Molecular modeling informed by nOe studies reveal high degree complementarity between 6 8, which very similar to found natural galectins.