Regioselective hydrolysis of peracetylated alpha-D-glycopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis

Bioorg Med Chem Lett. 1999 Feb 22;9(4):633-6. doi: 10.1016/s0960-894x(99)00053-0.

Abstract

Penta-O-acetyl-alpha-D-glucopyranose was selectively deacetylated in aqueous media by lipases from Candida cilindracea (CCL) adsorbed on octyl-agarose support. Enzymatic hydrolyses was regioselective at the 4-position under neutral pH and towards the 6 position under acidic conditions. This enzymatic approach allows the one step synthesis of 1,2,3,6-tetra-O-acetyl-alpha-D-glucopyranoses 1, a useful intermediate in oligosaccharide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Catalysis
  • Enzymes, Immobilized / metabolism*
  • Glucose / analogs & derivatives*
  • Glucose / chemistry
  • Glucose / metabolism
  • Hydrolysis
  • Lipase / metabolism*
  • Magnetic Resonance Spectroscopy
  • Oligosaccharides / chemical synthesis*
  • Water / chemistry

Substances

  • Enzymes, Immobilized
  • Oligosaccharides
  • Water
  • glucose pentaacetate
  • Lipase
  • Glucose