Correlation between structure of the lactones and substance specificity in enzyme-catalyzed polymerization for the synthesis of polyesters

Yoichi Suzuki, Seiichi Taguchi, Tamao Hisano, Kazunobu Toshima, Shuichi Matsumura, Yoshiharu Doi

研究成果: Article査読

18 被引用数 (Scopus)

抄録

Small-size (4-membered) and medium-size (5-, 6-, and 7-membered) unsubstituted lactones as well as unsubstituted macrolides (12 and 13 membered) were subjected to the ring-opening polymerization using the extracellular PHB depolymerase from Alcaligenes faecalis T1 (PhaZAfa). The characteristic reactivities of the lactones were discussed based on a tertiary structure model of the active site of the PhaZAfa. With respect to the ring-size of the lactones, the 4-membered β-propiolactone and 6-membered δ-valerolactone (δ-VL) showed the highest polymerization activity, and δ-VL seemed to be the upper size limit for the molecular recognition of the narrow active site cleft of PhaZAfa. On the other hand, ε-caprolactone, 11-undecanolide, and 12-dodecanolide, which showed excellent polymerization activities by lipases, were scarcely polymerized by PhaZAfa. This was ascribed to the difference in the recognition sites between PhaZAfa and lipase. In addition, the effect of the substrate-binding domain of PhaZAfa and the enantioselective ring-opening polymerization of (R,S)-β-butyrolactone ((R,S)-β-BL) were studied. The substrate-binding domain lacking PhaZAfa showed higher reactivities than PhaZAfa for the polymerization of the lactones and that a significant enantioselectivity was observed at the early stage of the polymerization of (R,S)-β-BL to produce the (R )-enriched optically active poly(3-hydroxybutyrate).

本文言語English
ページ(範囲)537-543
ページ数7
ジャーナルBiomacromolecules
4
3
DOI
出版ステータスPublished - 2003 5月 1

ASJC Scopus subject areas

  • バイオエンジニアリング
  • 生体材料
  • ポリマーおよびプラスチック
  • 材料化学

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