Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages

Taisuke Banno, Kazuo Kawada, Shuichi Matsumura

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Abstract: Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of w-alkyl 7V,7V-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the 7V,7V-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.

Original languageEnglish
Pages (from-to)185-195
Number of pages11
JournalJournal of Oleo Science
Volume60
Issue number4
Publication statusPublished - 2011

Fingerprint

Carbonates
Stereochemistry
Amino alcohols
Amino Alcohols
Biodegradability
Lipases
Lipase
Surface-Active Agents
Hydrolysis
Surface active agents

Keywords

  • Biodegradability
  • Carbonate linkage
  • Lipase
  • Quaternary ammonium-type cationics
  • Stereochemistry

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages. / Banno, Taisuke; Kawada, Kazuo; Matsumura, Shuichi.

In: Journal of Oleo Science, Vol. 60, No. 4, 2011, p. 185-195.

Research output: Contribution to journalArticle

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N2 - Abstract: Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of w-alkyl 7V,7V-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the 7V,7V-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.

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