Enzymatic synthesis of a novel cyclic pentasaccharide consisting of alpha-D-glucopyranose with 6-alpha-glucosyltransferase and 3-alpha-isomaltosyltransferase

Carbohydr Res. 2005 Jul 4;340(9):1577-82. doi: 10.1016/j.carres.2005.04.017.

Abstract

A novel cyclic pentasaccharide (CPS) and a branched cyclic pentasaccharide (6G-CPS) consisting of d-glucopyranose were synthesized with 6-alpha-glucosyltransferase (6GT) and 3-alpha-isomaltosyltransferase (IMT) from Bacillus globisporus N75. The structure of CPS was cyclo-[-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->]. The other, 6G-CPS, had the structure cyclo-[-->6)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(1-->3)-[alpha-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->]. The formation of CPS was presumed to occur after the following four successive reactions: a 6-glucosyltransfer reaction with 6GT, a 4-glucosyltransfer reaction with 6GT, a 3-isomaltosyltransfer reaction with IMT, and a cyclization reaction with IMT.

MeSH terms

  • Bacillus / enzymology
  • Carbohydrate Sequence
  • Glucose / chemistry
  • Glucosyltransferases / metabolism*
  • Macrocyclic Compounds / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / biosynthesis*
  • Oligosaccharides / chemistry
  • Starch / chemistry

Substances

  • Macrocyclic Compounds
  • Oligosaccharides
  • cyclo(-6)-glucpyranosyl-1-3-glucopyranosyl-1-6-glucopyranosyl-1-3-(glucopyranosyl-1-6)-glucopyranosyl-1-4-glucopyranosyl-(1-)
  • cyclo(-6)-glucpyranosyl-1-3-glucopyranosyl-1-6-glucopyranosyl-1-3-glucopyranosyl-1-4-glucopyranosyl-(1-)
  • Starch
  • Glucosyltransferases
  • maltosyltransferase
  • Glucose