Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

Abstract

The relationship between molecular structure and physical properties of monolayers of complexes between an amphiphilic, steroidal cholesterol-substituted phenylboronic acid (1) and mono-saccharides was studied at the air–water interface. Phase transition, compressibility and limiting molecular area of monolayers of 1 in the presence of monosaccharides are correlated with the calculated structures of the phenylboronic acid–monosaccharide complexes. The monolayer of 1 exhibits chiral discrimination towards optical isomers of monosaccharides. The phase transition during compression of monolayers of 1 is discussed to reflect rearranged binding positions between the boronic acid and monosaccharides.