Direct enzymatic synthesis of a polyester with free pendant mercapto groups

Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

45 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 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.

Original languageEnglish
Pages (from-to)366-373
Number of pages8
JournalBiomacromolecules
Volume10
Issue number2
DOIs
Publication statusPublished - 2009 Feb 9

Fingerprint

Polyesters
Lipases
Polycondensation
Lipase
Disulfides
Dimethyl sulfoxide
Candida
Hexanes
Dimethyl Sulfoxide
Hexane
Sulfhydryl Compounds
Copolymerization
Gels
Monomers
Oxidation
Air

ASJC Scopus subject areas

  • Bioengineering
  • Materials Chemistry
  • Polymers and Plastics
  • Biomaterials

Cite this

Direct enzymatic synthesis of a polyester with free pendant mercapto groups. / Kato, Makoto; Toshima, Kazunobu; Matsumura, Shuichi.

In: Biomacromolecules, Vol. 10, No. 2, 09.02.2009, p. 366-373.

Research output: Contribution to journalArticle

Kato, Makoto ; Toshima, Kazunobu ; Matsumura, Shuichi. / Direct enzymatic synthesis of a polyester with free pendant mercapto groups. In: Biomacromolecules. 2009 ; Vol. 10, No. 2. pp. 366-373.
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