Synthesis of glycosyl-trehaloses by cyclomaltodextrin glucanotransferase through the transglycosylation reaction

Biosci Biotechnol Biochem. 1997 Jul;61(7):1146-9. doi: 10.1271/bbb.61.1146.

Abstract

Cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus produced a series of glycosyl-trehaloses through the transglycosylation reaction with cyclomaltohexaose as the glycosyl donor and trehalose as its acceptor. After beta-amylase treatment, five species of glycosyl-trehaloses were isolated by column chromatography. After chemical and enzymatic analyses, it was concluded that these oligosaccharides were alpha-maltosyl alpha-D-glucopyranoside, alpha-maltotriosyl alpha-D-glucopyranoside, alpha-maltosyl alpha-maltoside, alpha-maltotriosyl alpha-maltoside, and alpha-maltotriosyl alpha-maltotrioside. These were not hydrolyzed by salivary amylase, artificial gastric juice, or pancreatic amylase, however they were hydrolyzed by enzymes of the small intestine.

MeSH terms

  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Geobacillus stearothermophilus / enzymology
  • Glucan 1,4-alpha-Glucosidase / chemistry
  • Glucan 1,4-alpha-Glucosidase / metabolism
  • Glucose / chemistry
  • Glucose / metabolism*
  • Glucosyltransferases / chemistry
  • Glucosyltransferases / metabolism*
  • Glycosylation
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry / methods
  • Molecular Sequence Data
  • Oligosaccharides / chemistry
  • Oligosaccharides / metabolism
  • Optics and Photonics
  • Trehalose / chemical synthesis*
  • Trehalose / metabolism*

Substances

  • Oligosaccharides
  • Trehalose
  • Glucosyltransferases
  • cyclomaltodextrin glucanotransferase
  • Glucan 1,4-alpha-Glucosidase
  • Glucose