Direct enzymatic synthesis of a polyester with free pendant mercapto groups

Makoto Kato; Kazunobu Toshima; Shuichi Matsumura

doi:10.1021/bm801132d

Direct enzymatic synthesis of a polyester with free pendant mercapto groups

Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

Department of Applied Chemistry

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

50 Citations (Scopus)

Abstract

An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate. The polycondensation reaction using immobilized lipase from Candida antarctica (lipase CA) was carried out in bulk at 70 °C without any formation of disulfide or thioester linkages to produce the corresponding polyester with M_w = 14000 g/mol in high yield. The content of free mercapto groups in the polyester could be controlled by copolymerization with other monomers. The obtained polyester was easily cross-linked to form gels by the air oxidation of the pendant thiols to disulfides in dimethyl sulfoxide.

Original language	English
Pages (from-to)	366-373
Number of pages	8
Journal	Biomacromolecules
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/bm801132d
Publication status	Published - 2009 Feb 9

ASJC Scopus subject areas

Bioengineering
Biomaterials
Polymers and Plastics
Materials Chemistry

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10.1021/bm801132d

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abstract = "An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate. The polycondensation reaction using immobilized lipase from Candida antarctica (lipase CA) was carried out in bulk at 70 °C without any formation of disulfide or thioester linkages to produce the corresponding polyester with Mw = 14000 g/mol in high yield. The content of free mercapto groups in the polyester could be controlled by copolymerization with other monomers. The obtained polyester was easily cross-linked to form gels by the air oxidation of the pendant thiols to disulfides in dimethyl sulfoxide.",

author = "Makoto Kato and Kazunobu Toshima and Shuichi Matsumura",

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AU - Kato, Makoto

AU - Toshima, Kazunobu

AU - Matsumura, Shuichi

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N2 - An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate. The polycondensation reaction using immobilized lipase from Candida antarctica (lipase CA) was carried out in bulk at 70 °C without any formation of disulfide or thioester linkages to produce the corresponding polyester with Mw = 14000 g/mol in high yield. The content of free mercapto groups in the polyester could be controlled by copolymerization with other monomers. The obtained polyester was easily cross-linked to form gels by the air oxidation of the pendant thiols to disulfides in dimethyl sulfoxide.

AB - An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate. The polycondensation reaction using immobilized lipase from Candida antarctica (lipase CA) was carried out in bulk at 70 °C without any formation of disulfide or thioester linkages to produce the corresponding polyester with Mw = 14000 g/mol in high yield. The content of free mercapto groups in the polyester could be controlled by copolymerization with other monomers. The obtained polyester was easily cross-linked to form gels by the air oxidation of the pendant thiols to disulfides in dimethyl sulfoxide.

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ER -

Direct enzymatic synthesis of a polyester with free pendant mercapto groups

Abstract

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