Synthesis of amphiphilic chitopentaose and chitoheptaose derivatives usinga common disaccharidic synthon as the chain elongation unit

With interest in clustering bioactive chitooligosaccharides, a pair of amph iphilic derivatives of around DP (degree of polymerization) 6, which has be en considered to be the minimum molecular length for some kinds of bioactiv ity, was synthesized. Homologous derivatives of chitopentaose and chitohept aose carrying tetradecanoyl and tetradecyloxy groups at the NH and C-1 of t he reducing ends, respectively, were actually obtained using a 1,6-anhydro- 2-azido-2-deoxy-beta-D-glucopyranose derivative as the terminal precursor a nd a chitobiose derivative as the elongation unit. Micelle formation of bot h derivatives was assumed from the results obtained by dye solubilization t ests.