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Lipase‐Catalyzed Transformation of Unnatural‐Type Poly(3‐hydroxybutanoate) into Reactive Cyclic Oligomer
Author(s) -
Osanai Yasushi,
Toshima Kazunobu,
Yoshie Naoko,
Inoue Yoshio,
Matsumura Shuichi
Publication year - 2002
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/1616-5195(20020201)2:2<88::aid-mabi88>3.0.co;2-5
Subject(s) - oligomer , tacticity , chemistry , polymer chemistry , lipase , alkyl , candida antarctica , solvent , catalysis , polymer , organic chemistry , polymerization , enzyme
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.