Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters

Methyl, ethyl and butyl β-D-glucosaminide 6-O-fatty acid esters were prepared by the novel direct transglycosylation reaction of chitosan with methanol, ethanol and butanol using resting cells of the chitosan-assimilating strain, Penicillium sp. KS018 as the enzyme source of exo-β -D-GlcNase followed by the transesterification reaction with the fatty acid methyl ester using lipase. Transesterification by the lipase depended on enzyme origin, and reaction conditions, such as temperature and reaction pressure. Methyl, ethyl and butyl β-D-glucosaminide 6-O-fatty acid monoesters demonstrated excellent surface activity in aqueous solution. The antimicrobial properties of the 6-O-dodecanoyl-glucosaminides were stronger compared to dodecyl β-D-glucoside. The methyl, ethyl and butyl glucosaminide 6-O-fatty acid esters were all readily biodegradable by activated sludge.