Enzymatic synthesis of polythioester by the ring-opening polymerization of cyclic thioester

Biomacromolecules. 2007 Nov;8(11):3590-6. doi: 10.1021/bm700623s. Epub 2007 Oct 18.

Abstract

A high molecular weight aliphatic polythioester was prepared by lipase-catalyzed polymerization of hexane-1,6-dithiol and dimethyl sebacate using the technique of ring-opening polymerization of a cyclic thioester. The cyclic thioester monomer was first prepared using lipase from Candida antarctica in dilute solution. The monomer was then polymerized by the same lipase in bulk to produce a polythioester with an M(w) of about 120 000 g/mol, which was significantly higher than that of a polythioester obtained by direct polycondensation of the dithiol and diacid. The polymerization rate and thermal properties of the product were measured and compared with those of the corresponding polyester prepared by ring-opening polymerization of a cyclic ester.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Esters / chemistry*
  • Fungal Proteins
  • Lipase / metabolism*
  • Mass Spectrometry
  • Molecular Structure
  • Polymers / chemistry*
  • Polymers / metabolism*
  • Sulfhydryl Compounds / chemistry*
  • Temperature

Substances

  • Esters
  • Fungal Proteins
  • Polymers
  • Sulfhydryl Compounds
  • Lipase
  • lipase B, Candida antarctica