Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters

Tooru Sagoh, Kazunobu Toshima, Kazuo Kawada, Shuichi Matsumura

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)597-606
Number of pages10
JournalJournal of oleo science
Volume52
Issue number11
DOIs
Publication statusPublished - 2003 Jan 1

Keywords

  • biodegradation
  • chitosan
  • enzymatic synthesis
  • glucosaminide fatty acid ester
  • sugar based surfactant
  • surface activity
  • transglycosylation

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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