Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine-Phenol Alternating Oligomer

An amphiphilic pyridine-phenol alternating oligomer, in which oligo(ethylene glycol) chains are attached at the 4-positions of the pyridine and the phenol rings, was synthesized as a helical host to realize saccharide recognition in water. This oligomer was soluble not only in less-polar solvents but also in water at room temperature. Circular dichroism investigations revealed that the oligomer could recognize several kinds of saccharides and their derivatives including glycodrugs to form chiral higher-order structures in water. Especially, the oligomer showed high affinity for D-glucosamine, and their association constants were over 10³ M¯¹.