Enzymatic synthesis of N-acetylglucosaminyl-cyclodextrin by the reverse reaction of N-acetylhexosaminidase from jack bean

Biosci Biotechnol Biochem. 1999 Oct;63(10):1677-83. doi: 10.1271/bbb.63.1677.

Abstract

Novel heterobranched cyclodextrins (CDs), N-acetylglucosaminyl-cyclodextrins (GlcNAc-CD), were synthesized from a mixture of GlcNAc and alpha, beta, or gamma CD by the reverse reaction of N-acetylhexosaminidase from jack bean. Optimum pH and temperature for the production of GlcNAc-alpha CD by N-acetylhexosaminidase were pH 4.9 and 50-70 degrees C, respectively. The maximum yield of GlcNAc-alpha CD was 17.5% (mol/mol) at the concentration of 1 M GlcNAc and 0.25 M alpha CD. The reverse reaction product, GlcNAc-alpha CD, was separated into two peaks by HPLC analysis on the ODS column. Their structures were identified as 6-O-beta-D-N-acetylglucosaminyl-alpha CD and 2-O-beta-D-N-acetylglucosaminyl-alpha CD by FAB-MS and NMR spectroscopies. N-Acetylhexosaminidase from jack bean also synthesized N-acetylgalactosaminyl-alpha CD from N-acetylgalactosamine and alpha CD.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography / methods
  • Cyclodextrins / chemical synthesis*
  • Cyclodextrins / chemistry
  • Drug Carriers / chemical synthesis
  • Fabaceae / enzymology*
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Plants, Medicinal*
  • Temperature
  • Time Factors
  • alpha-Cyclodextrins*
  • beta-N-Acetylhexosaminidases / chemistry*
  • beta-N-Acetylhexosaminidases / metabolism*

Substances

  • 2-O-(N-acetylglucosaminyl)-alpha-cyclodextrin
  • Cyclodextrins
  • Drug Carriers
  • alpha-Cyclodextrins
  • beta-N-Acetylhexosaminidases