Nonplanar Macrocycle Consisting of Four Pyridine and Phenol Units Connected with Acetylene Bonds Displaying Preferential Binding to Maltoside over Monosaccharides

摘要

A nonplanar macrocycle consisting of four pyridine–acetylene–phenol units was developed as a host for saccharide guest molecules. The macrocycle was found to strongly associate with a lipophilic maltose derivative, with an association constant of 10~(7) M~(–1), over monosaccharide derivatives, for which much smaller association constants were determined, ranging from 10~(3) M~(–1) to 10~(4) M~(–1). The macrocycle was found to adopt a boat-like conformation, encapsulating β-d-maltoside in a twisted manner through approximately seven intermolecular hydrogen bonds.