Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

Biotechnol Lett. 2010 Oct;32(10):1463-71. doi: 10.1007/s10529-010-0311-z. Epub 2010 May 22.

Abstract

Copolymeric polyoxoesters containing branched-chain methylenethiol functions, i.e., poly(1,12-dodecanedioic acid-co-1-thioglycerol) and poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol), were formed by lipase-catalyzed polyesterification and polytransesterification of 1,12-dodecanedioic acid and diethyl 1,12-dodecanedioate, respectively, with 1-thioglycerol (3-mercaptopropane-1,2-diol) using immobilized lipase B from Candida antarctica (Novozym 435) in vacuo without drying agent in the reaction mixture. After 360-480 h, both polyoxoesters were purified by extraction from the reaction mixtures followed by solvent fractionation. The precipitate of poly(1,12-dodecanedioic acid-co-1-thioglycerol) demonstrated a M(W) of ~170,000 Da, whereas a M(W) of ~7,100 Da only was found for poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol). Both polycondensates were analyzed by GPC/SEC, alkali-catalyzed transmethylation, NMR- and FTIR-spectrometry.

MeSH terms

  • Candida / enzymology*
  • Chromatography, Gel
  • Dicarboxylic Acids / metabolism*
  • Enzymes, Immobilized / metabolism
  • Esterification
  • Fungal Proteins
  • Gas Chromatography-Mass Spectrometry
  • Glycerol / analogs & derivatives*
  • Glycerol / metabolism
  • Lipase / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Weight
  • Polyesters / chemistry
  • Polyesters / isolation & purification
  • Polyesters / metabolism*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Dicarboxylic Acids
  • Enzymes, Immobilized
  • Fungal Proteins
  • Polyesters
  • dodecanedioic acid
  • thioglycerol
  • Lipase
  • lipase B, Candida antarctica
  • Glycerol