Enzymatic synthesis of a 2-O-alpha-D-glucopyranosyl cyclic tetrasaccharide by kojibiose phosphorylase

Carbohydr Res. 2005 Feb 28;340(3):449-54. doi: 10.1016/j.carres.2004.12.012.

Abstract

The glucosyl transfer reaction of kojibiose phosphorylase (KPase) from Thermoanaerobacter brockii ATCC35047 was examined using cyclo-{-->6)-alpha-d-Glcp-(1-->3)-alpha-d-Glcp-(1-->6)-alpha-d-Glcp-(1-->3)-alpha-d-Glcp-(1-->} (CTS) as an acceptor. KPase produced four transfer products, saccharides 1-4. The structure of a major product, saccharide 4, was 2-O-alpha-d-glucopyranosyl-CTS, cyclo-{-->6)-alpha-d-Glcp-(1-->3)-alpha-d-Glcp-(1-->6)-[alpha-d-Glcp-(1-->2)]-alpha-d-Glcp-(1-->3)-alpha-d-Glcp-(1-->}. The other transfer products, saccharides 1-3, were 2-O-alpha-kojibiosyl-, 2-O-alpha-kojitriosyl-, and 2-O-alpha-kojitetraosyl-CTS, respectively. These results showed that KPase transferred a glucose residue to the C-2 position at the ring glucose residue of CTS. This enzyme also catalyzed the chain-extending reaction of the side chain of 2-O-alpha-d-glycopyranosyl-CTS.

MeSH terms

  • Carbohydrate Sequence
  • Cyclodextrins / chemistry*
  • Disaccharides / chemistry*
  • Molecular Sequence Data
  • Oligosaccharides / chemistry*
  • Phosphorylases / chemistry*
  • Phosphorylases / isolation & purification
  • Thermoanaerobacter / enzymology*

Substances

  • Cyclodextrins
  • Disaccharides
  • Oligosaccharides
  • cyclo-tetra-glucose
  • kojibiose
  • Phosphorylases