Synthesis and characterization of water-soluble glucosyloxyethyl acrylate modified chitosan

Int J Biol Macromol. 2011 Jun 1;48(5):753-7. doi: 10.1016/j.ijbiomac.2011.02.018. Epub 2011 Mar 4.

Abstract

A novel water-soluble chitosan derivative, glucosyloxyethyl acrylated chitosan was successfully synthesized by Michael addition reaction of chitosan with glucosyloxyethyl acrylate (GEA), and the obtained glyco-chitosan derivative was characterized by FT-IR, (1)H NMR, elemental analysis, XRD, TG, DSC and SEM. The FT-IR and (1)H NMR results showed that GEA residues were grafted onto the amino group of chitosan. The degree of substitution (DS) was calculated by elemental analysis. XRD data revealed that the introduced saccharide moieties decreased the crystalline structure of chitosan. TG and DSC results demonstrated that the glucosyloxyethyl acrylated chitosan was less thermal stable than chitosan. This efficient synthetic method provided an approach of preparing water-soluble glyco-chitosan derivatives. The obtained derivatives would show stronger specific affinity of lectin than chitosan thus would have potential applications in biomaterials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Chitosan* / analogs & derivatives
  • Chitosan* / chemical synthesis
  • Chitosan* / chemistry
  • Microscopy, Electron, Scanning
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry*
  • X-Ray Diffraction

Substances

  • Biocompatible Materials
  • Water
  • Chitosan