Synthesis, characterization, and reverse-micellar studies of some N-substituted derivatives of 6-amino-6-deoxy-1,2-O-isopropylidene-d-glucose

Dry heating of N-substituted hexadecylamines with 5,6-anhydro-1,2-O-isopropylidene-α-d-glucofuranose afforded glucose-based nonionic surfactants having a tertiary amino group linked to C-6 of the glucose moiety. These surfactants were tested for the solubilization of the l-amino acids tryptophan, tyrosine, phenylalanine, and cysteine in n-hexane. Reverse-micellar measurements revealed that (6,6′-hexadecylimino)bis(6-deoxy-1,2-O-isopropylidene)-α-d-glucofuranose is the most effective surfactant.