TY - JOUR
T1 - Lipase-catalyzed transformation of unnatural-type poly(3-hydroxybutanoate) into reactive cyclic oligomer
AU - Osanai, Yasushi
AU - Toshima, Kazunobu
AU - Yoshie, Naoko
AU - Inoue, Yoshio
AU - Matsumura, Shuichi
PY - 2002/3/15
Y1 - 2002/3/15
N2 - 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.
AB - 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.
KW - Biodegradable
KW - Enzymes
KW - Lipase catalysis
KW - Poly[(R,S)-3-hydroxybutanoate] (P(3HB))
KW - Polyesters
KW - Structure
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M3 - Article
AN - SCOPUS:0037088502
VL - 203
SP - 88
EP - 94
JO - Macromolecular Chemistry and Physics
JF - Macromolecular Chemistry and Physics
SN - 1022-1352
IS - 4
ER -