Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters

Tooru SAGOH, Kazunobu TOSHIMA, Kazuo KAWADA, Shuichi MATSUMURA
2003 Journal of Oleo Science  
Methyl, ethyl and butyl b-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-b-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
more » ... mperature and reaction pressure. Methyl, ethyl and butyl b-Dglucosaminide 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 b-D-glucoside. The methyl, ethyl and butyl glucosaminide 6-O-fatty acid esters were all readily biodegradable by activated sludge.
doi:10.5650/jos.52.597 fatcat:nfpjdqp6u5a23fqpozyjfirfqq