Lipase-catalyzed transformation of unnatural-type poly(3-hydroxybutanoate) into reactive cyclic oligomer

Yasushi Osanai, Kazunobu Toshima, Naoko Yoshie, Yoshio Inoue, Shuichi Matsumura

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Unnatural-type syndiotactic and atactic poly[(R,S)-3-hydroxybutanoate]s [P(3HB)s] were enzymatically transformed into a reactive cyclic 3HB oligomer of molecular weight ca. 500 in an organic solvent, such as toluene, using immobilized lipase from Candida antarctica at 40°C for 24 h. It was confirmed that similar results were obtained for both syndiotactic and atactic P(3HB)s. On the other hand, the acidic degradation of these polymers using a protonic acid, such as p-toluenesulfonic acid, exclusively produced the linear 3HB oligomer instead of the cyclic oligomer. The formation of the cyclic oligomer was regarded as the characteristic feature of the lipase-catalyzed degradation in organic media. The cyclic oligomer obtained readily reacted with alcohol as a nucleophile, and using lipase, to produce the alkyl ester of the 3HB oligomer.

Original languageEnglish
Pages (from-to)88-94
Number of pages7
JournalMacromolecular Bioscience
Volume2
Issue number2
DOIs
Publication statusPublished - 2002 Dec 1

Keywords

  • Biodegradable
  • Enzymes
  • Lipase catalysis
  • Poly[(R,S)-3- hydroxybutanoate](P(3HB))
  • Polyesters
  • Structure

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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