Production of 1,5-anhydro-d-fructose by an α-glucosidase belonging to glycoside hydrolase family 31

Biosci Biotechnol Biochem. 2014;78(12):2064-8. doi: 10.1080/09168451.2014.943651. Epub 2014 Aug 5.

Abstract

α-1,4-Glucan lyases [glycoside hydrolase family (GH) 31] catalyze an elimination reaction to form 1,5-anhydro-d-fructose (AF), while GH31 α-glucosidases normally catalyze a hydrolytic reaction. We determined that a small amount of AF was produced by GH31 Aspergillus niger α-glucosidase from maltooligosaccharides by elimination reaction, likely via an oxocarbenium ion intermediate.

Keywords: 1,5-anhydro-d-fructose; GH31 α-glucosidase; elimination mechanism.

MeSH terms

  • Aspergillus niger / chemistry*
  • Aspergillus niger / enzymology
  • Biocatalysis
  • Carbohydrate Conformation
  • Carbon Isotopes
  • Fructose / analogs & derivatives*
  • Fructose / chemistry
  • Fungal Proteins / chemistry*
  • Fungal Proteins / isolation & purification
  • Hydrolysis
  • Kinetics
  • Oligosaccharides / chemistry*
  • alpha-Glucosidases / chemistry*
  • alpha-Glucosidases / isolation & purification

Substances

  • Carbon Isotopes
  • Fungal Proteins
  • Oligosaccharides
  • maltooligosaccharides
  • Fructose
  • 1,5-anhydrofructose
  • alpha-Glucosidases