Chemical synthesis of 6'-alpha-maltosyl-maltotriose, a branched oligosaccharide representing the branch point of starch

Carbohydr Res. 1995 Nov 7;277(1):109-23. doi: 10.1016/0008-6215(95)00203-6.

Abstract

Chemical synthesis of the branched pentasaccharide 6'-alpha-maltosyl-maltotriose (15) is reported, based on the use of one synthon as a glycosyl acceptor and another synthon as a glycosyl donor. The synthon used as glycosyl acceptor was phenyl 2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (7) and was synthesized from D-glucose with phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside and phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside as key intermediates. The synthon used as glycosyl donor was O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-O-(2,3,6-tri-O -benzyl - alpha-D-glucopyranosyl)-(1-->6)-O-[(2,3,4,6-tetra-O-benzyl-alpha-D- glucopyranosyl)-(1-->4)]-2,3-di-O-benzyl-alpha,beta-D-glucopyranosyl trichloroacetimidate (12) and was synthesized from phenyl O-2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-O-(2,3,6-tri-O- benzyl- alpha-D-glucopyranosyl)-(1-->6)-O-[(2,3,4,6-tetra-O-acetyl-alpha-D- glucopyranosyl)-(1-->4)]-2,3-di-O-acetyl-1-thio-beta-D-glucopyranoside with O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-O-(2,3,6-tri-O - benzyl-alpha-D-glucopyranosyl)-(1-->4)]-2,3-di-O-benzyl-D-glucopyranose as an intermediate. Condensation of compounds 7 and 12 followed by removal of the phenylthio group and debenzylation provided the branched pentasaccharide 15. Alternatively, the branched pentasaccharide was produced from amylopectin by consecutive alpha- and beta-amylase treatments and purified by chromatography. The identity of the products obtained by chemical synthesis and enzymatic hydrolysis is documented by 1H and 13C NMR spectra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, Gel
  • Chromatography, Ion Exchange
  • Magnetic Resonance Spectroscopy
  • Maltose / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Oligosaccharides / isolation & purification
  • Starch / chemistry*
  • Thioglycosides / chemical synthesis
  • Thioglycosides / chemistry
  • alpha-Amylases / metabolism

Substances

  • 6'-maltosylmaltotriose
  • Oligosaccharides
  • Thioglycosides
  • Maltose
  • Starch
  • alpha-Amylases