Polyol Structure Influences Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Polyesters

Biotechnol J. 2017 Sep;12(9). doi: 10.1002/biot.201600741. Epub 2017 Aug 10.

Abstract

Polyesters of 2,5-furandicarboxylic acid (FDCA) have gained attention as they can be regarded as the bio-based alternatives to the petroleum-based polyesters of terephthalic acid. However, only little is known about the biodegradation and enzymatic hydrolysis of FDCA-based polyesters. This work aims to investigate the influence of different polyols on enzymatic hydrolysis of FDCA-based polyesters. A series of polyesters containing various polyols are synthesized and analyzed regarding susceptibility to enzymatic hydrolysis by cutinase 1 from Thermobifida cellulosilytica (Thc_Cut1). FDCA-based polyesters' number average molecular weight (Mn ) ranged from 9360-35 800 g mol-1 according to gel permeation chromatography (GPC) analysis. Differential scanning calorimetry (DSC) analyses show decreasing glass transition temperature (Tg ) with increasing diol chain length. Crystallinity of all polyesters is below 1% except for polyesters containing 1,6-hexanediol, 1,8-octanediol, and 1,12-dodecanediol for which calculated crystallinities are 27, 37, and 30%, respectively. Thc_Cut1 hydrolyzes all tested polyesters with preference for polyesters containing 1,5-pentanediol and 1,9-nonanediol (57.7 ± 7.5 and 52.8 ± 4.0% released FDCA). Enzyme activity increases when the linear diol 1,3-propanediol is replaced by the branched analog 1,2-propanediol or ethoxy units are introduced into the polyester chain. The results will contribute to expand the knowledge of microbial biodegradation of FDCA-based polyesters.

Keywords: Thermobifida cellulosilytica; bio-based; cutinase; degradation; renewable building blocks.

MeSH terms

  • Actinobacteria / enzymology
  • Carboxylic Ester Hydrolases / metabolism*
  • Dicarboxylic Acids / analysis
  • Dicarboxylic Acids / chemistry
  • Dicarboxylic Acids / metabolism*
  • Furans / analysis
  • Furans / chemistry
  • Furans / metabolism*
  • Hydrolysis
  • Magnetic Resonance Imaging
  • Polyesters / analysis
  • Polyesters / chemistry
  • Polyesters / metabolism*
  • Polymers / chemistry*
  • Polymers / metabolism

Substances

  • Dicarboxylic Acids
  • Furans
  • Polyesters
  • Polymers
  • polyol
  • 2,5-furandicarboxylic acid
  • Carboxylic Ester Hydrolases
  • cutinase