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

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(3BHB)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 oligimer 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 Chemistry and Physics
Volume203
Issue number4
Publication statusPublished - 2002 Mar 15

Fingerprint

Lipases
Lipase
oligomers
Oligomers
degradation
Degradation
Nucleophiles
acids
Acids
Candida
nucleophiles
Toluene
Antarctic regions
Organic solvents
toluene
esters
molecular weight
Esters
Polymers
alcohols

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Lipase-catalyzed transformation of unnatural-type poly(3-hydroxybutanoate) into reactive cyclic oligomer. / Osanai, Yasushi; Toshima, Kazunobu; Yoshie, Naoko; Inoue, Yoshio; Matsumura, Shuichi.

In: Macromolecular Chemistry and Physics, Vol. 203, No. 4, 15.03.2002, p. 88-94.

Research output: Contribution to journalArticle

Osanai, Yasushi ; Toshima, Kazunobu ; Yoshie, Naoko ; Inoue, Yoshio ; Matsumura, Shuichi. / Lipase-catalyzed transformation of unnatural-type poly(3-hydroxybutanoate) into reactive cyclic oligomer. In: Macromolecular Chemistry and Physics. 2002 ; Vol. 203, No. 4. pp. 88-94.
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