Synthesis and characterization of oligomaltose-grafted lipids with application to liposomes

Novel glycolipids, which contain 2 and 15 oligomaltose units and a phosphatidylethanolamine, were synthesized and characterized by FTIR and (1)H-NMR spectroscopies. The well-defined linear structure of the glycolipids was assured by an end-point conjugation strategy using selective oxidation of the reducing end groups of maltose oligosaccharides, followed by aminolysis with distearoylphosphatidylethanolamine. The intermediate acids react selectively with amines to form amide linkages, catalyzed by 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide. Conformations of the glycolipids at the air-water interface were proposed based on the film balance measurements. The unique conformations of glycolipids at interfaces may offer advantages over traditional PEO-derived lipids in regard to their applications for sterically stabilizing liposomes. The glycolipids demonstrated the ability for sterically stabilizing liposome dispersions, as determined by turbidity measurements.