Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters

Tooru Sagoh, Kazunobu Toshima, Kazuo Kawada, Shuichi Matsumura

研究成果: Article

3 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)597-606
ページ数10
ジャーナルJournal of Oleo Science
52
発行部数11
DOI
出版物ステータスPublished - 2003

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Fatty acids
Esters
Fatty Acids
Transesterification
Lipases
Chitosan
Lipase
Enzymes
Butanols
Glucosides
Butenes
Methanol
Ethanol
Temperature

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

これを引用

Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters. / Sagoh, Tooru; Toshima, Kazunobu; Kawada, Kazuo; Matsumura, Shuichi.

:: Journal of Oleo Science, 巻 52, 番号 11, 2003, p. 597-606.

研究成果: Article

Sagoh, Tooru ; Toshima, Kazunobu ; Kawada, Kazuo ; Matsumura, Shuichi. / Enzymatic Synthesis of Surface Active and Biodegradable Glucosaminide Fatty Acid Esters. :: Journal of Oleo Science. 2003 ; 巻 52, 番号 11. pp. 597-606.
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N2 - 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.

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KW - enzymatic synthesis

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