An Improved Synthetic Procedure for the Preparation of N-Acyl (2-aminoethyl)-β-d-glycopyranoside Lipids and Characterization of Their Mesogenic Properties

A modified synthetic procedure was used for the synthesis of N-acyl (2-aminoethyl) glycosides bearing lactose, maltose, and melibiose carbohydrate headgroups and different acyl chains. The lipid glycosides were prepared in gram scale and investigated for their liquid crystalline properties. It was found that the polar spacer suppresses polymorphism, and the resulting simplified phase behavior was found in the pure state upon heating, as well as for the lyotropic phases.