Synthesis of a chitosan tetramer derivative, beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-Glc N through a partial N-acetylation reaction by chitin deacetylase

Carbohydr Res. 2000 Apr 20;325(3):211-5. doi: 10.1016/s0008-6215(00)00004-5.

Abstract

We have synthesized beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-GlcN (2) through a partial N-acetylation reaction of chitosan tetramer 1 by a chitin deacetylase from Colletotrichum lindemuthianum ATCC 56676. The compound was purified from the mixture of acetylation products of 1 using cation-exchange column chromatography and amine-adsorption column chromatography, and its structure was estimated by 1H NMR and FABMS analyses. The enzymatic reaction allows a regioselectivity that is hard to achieve by chemical N-acetylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Amidohydrolases / chemistry*
  • Carbohydrate Sequence
  • Chitin / analogs & derivatives*
  • Chitin / chemical synthesis
  • Chitosan
  • Colletotrichum / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Sequence Data
  • Time Factors

Substances

  • GlcNAc-(1-4)-GlcNAc-(1-4)-GlcNAc-(1-4)-GlcN
  • Chitin
  • Chitosan
  • Amidohydrolases
  • chitin deacetylase