Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid

Makoto Kato; Kazunobu Toshima; Shuichi Matsumura

doi:10.1021/bm050168i

Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid

Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 °C for 48 h to produce poly(11-mercaptoundecanoate) with an M_w of 34 000 in high yield. The 104.5 °C melting temperature (T_m) of poly(11-mercaptoundecanoate) was about 20 °C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling.

Original language	English
Pages (from-to)	2275-2280
Number of pages	6
Journal	Biomacromolecules
Volume	6
Issue number	4
DOIs	https://doi.org/10.1021/bm050168i
Publication status	Published - 2005 Jul 1

ASJC Scopus subject areas

Bioengineering
Biomaterials
Polymers and Plastics
Materials Chemistry

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AU - Matsumura, Shuichi

PY - 2005/7/1

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N2 - An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 °C for 48 h to produce poly(11-mercaptoundecanoate) with an Mw of 34 000 in high yield. The 104.5 °C melting temperature (Tm) of poly(11-mercaptoundecanoate) was about 20 °C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling.

AB - An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 °C for 48 h to produce poly(11-mercaptoundecanoate) with an Mw of 34 000 in high yield. The 104.5 °C melting temperature (Tm) of poly(11-mercaptoundecanoate) was about 20 °C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling.

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Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid

Abstract

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