N-(2-Carboxyethyl)chitosans: regioselective synthesis, characterisation and protolytic equilibria

Carbohydr Res. 2003 Jan 31;338(3):271-6. doi: 10.1016/s0008-6215(02)00432-9.

Abstract

N-(2-Carboxyethyl)chitosans were obtained by reaction of low molecular weight chitosan with a low degree of acetylation and 3-halopropionic acids under mild alkaline media (pH 8-9, NaHCO3) at 60 degrees C. The chemical structure of the derivatives obtained was determined by 1H and 13C NMR spectroscopies. It was found that alkylation of chitosan by 3-halopropionic acids proceeds exclusively at the amino groups. The products obtained are described in terms of their degrees of carboxyethylation and ratio of mono-, di-substitution and free amine content. The protonation constants of amino and carboxylate groups of a series of N-(2-carboxyethyl)chitosans were determined by pH-titration at ionic strength 0.1 M KNO3 and 25 degrees C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Chitin / analogs & derivatives*
  • Chitin / chemical synthesis*
  • Chitin / chemistry
  • Chitosan
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Static Electricity

Substances

  • Biocompatible Materials
  • Chitin
  • Chitosan