Transglycosylation of glycosyl residues to cyclic tetrasaccharide by Bacillus stearothermophilus cyclomaltodextrin glucanotransferase using cyclomaltodextrin as the glycosyl donor

Biosci Biotechnol Biochem. 2003 May;67(5):1094-100. doi: 10.1271/bbb.67.1094.

Abstract

Cyclomaltodextrin glucanotransferase (EC 2.4.1.19, abbreviated as CGTase) derived from Bacillus stearothermophilus produced a series of transfer products from a mixture of cyclomaltohexaose and cyclic tetrasaccharide (cyclo[-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->], CTS). Of the transfer products, only two components, saccharides A and D, remained and accumulated after digestion with glucoamylase. The total combined yield of the saccharides reached 63.4% of total sugars, and enzymatic and instrumental analyses revealed the structures of both saccharides. Saccharide A was identified as 4-mono-O-alpha-glucosyl-CTS, [-->6)-[alpha-D-Glcp-(1-->4)]-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->], and sachharide D was 4,4'-di-O-alpha-glucosyl-CTS, [-->6)-[alpha-D-Glcp-(1-->4)]-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->6)-[alpha-D-Glcp-(1-->4)]-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->]. These structures led us to conclude that the glycosyltransfer catalyzed by CGTase was specific to the C4-OH of the 6-linked glucopyranosyl residues in CTS.

MeSH terms

  • Aspergillus niger / enzymology
  • Bacillus / enzymology
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Geobacillus stearothermophilus / enzymology*
  • Glucan 1,4-alpha-Glucosidase / metabolism
  • Glucosyltransferases / chemistry*
  • Glycosides / chemistry*
  • Glycosylation
  • Hydrolysis
  • Mass Spectrometry
  • Methylation
  • Oligosaccharides / chemistry*
  • Polysaccharides / chemistry*
  • alpha-Glucosidases / metabolism
  • beta-Amylase / metabolism

Substances

  • Glycosides
  • Oligosaccharides
  • Polysaccharides
  • maltodextrin
  • Glucosyltransferases
  • cyclomaltodextrin glucanotransferase
  • beta-Amylase
  • alpha-Glucosidases
  • Glucan 1,4-alpha-Glucosidase