Enzymatically-synthesized xylo-oligosaccharides laurate esters as surfactants of interest

Carbohydr Res. 2020 Sep:495:108090. doi: 10.1016/j.carres.2020.108090. Epub 2020 Jul 18.

Abstract

Lipase-catalyzed synthesis of xylo-oligosaccharides esters from pure xylobiose, xylotriose and xylotetraose in the presence of vinyl laurate was investigated. The influence of different experimental parameters such as the loading of lipase, the reaction duration or the use of a co-solvent was studied and the reaction conditions were optimized with xylobiose. Under the best conditions, a regioselective esterification occurred to yield a monoester with the acyl chain at the OH-4 of the xylose unit at the non-reducing end. Surface-active properties of these pure xylo-oligosaccharides fatty esters have been evaluated. They display interesting surfactant activities that differ according to the degree of polymerization (DP) of the glycone moiety.

Keywords: Laurate ester; Lipase; Surfactant; Transesterification; Xylo-oligosaccharides.

MeSH terms

  • Basidiomycota / enzymology
  • Biocatalysis
  • Enzymes, Immobilized
  • Esters / chemistry
  • Esters / metabolism*
  • Fungal Proteins
  • Laurates / chemistry
  • Laurates / metabolism*
  • Lipase / metabolism*
  • Molecular Conformation
  • Oligosaccharides / biosynthesis*
  • Oligosaccharides / chemistry
  • Surface-Active Agents / chemistry
  • Surface-Active Agents / metabolism*
  • Xylose / biosynthesis*
  • Xylose / chemistry

Substances

  • Enzymes, Immobilized
  • Esters
  • Fungal Proteins
  • Laurates
  • Oligosaccharides
  • Surface-Active Agents
  • Xylose
  • Novozyme 435
  • Lipase

Supplementary concepts

  • Moesziomyces antarcticus