Chemical synthesis of methyl 6'-alpha-maltosyl-alpha-maltotrioside and its use for investigation of the action of starch synthase II

Carbohydr Res. 2003 Jan 20;338(2):189-97. doi: 10.1016/s0008-6215(02)00410-x.

Abstract

The branched pentasaccharide methyl 6'-alpha-maltosyl-alpha-maltotrioside was chemically synthesised and investigated as a primer for particulate starch synthase II (SSII) using starch granules prepared from the low-amylose pea mutant lam as the enzyme source. For chemical synthesis, the trichloroacetimidate activation method was used to synthesise methyl 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)]-O-(2,3-di-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside, which was then debenzylated to provide the desired branched pentasaccharide methyl 6'-alpha-maltosyl-alpha-maltotrioside as documented by 1H and 13C NMR spectroscopy. Using a large excess of the maltoside, the pentasaccharide was tested as a substrate for starch synthase II (SSII). Both of the non-reducing ends of methyl 6'-alpha-maltosyl-alpha-maltotrioside were extended equally resulting in two hexasaccharide products in nearly equal amounts. Thus, SSII catalyses an equimolar and non-processive elongation reaction of this substrate. Accordingly, the presence of the alpha-1,6 linkages does not dictate a specific structure of the pentasaccharide in which only one of the two non-reducing ends are available for extension.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Disaccharides / chemical synthesis*
  • Disaccharides / metabolism
  • Glucose / metabolism
  • Magnetic Resonance Spectroscopy
  • Maltose / analogs & derivatives
  • Maltose / chemical synthesis*
  • Maltose / metabolism
  • Oligosaccharides / biosynthesis
  • Oligosaccharides / chemistry
  • Oligosaccharides / isolation & purification
  • Plant Proteins*
  • Starch Synthase / metabolism*
  • Substrate Specificity
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / metabolism

Substances

  • Disaccharides
  • Oligosaccharides
  • Plant Proteins
  • Trisaccharides
  • methyl 6'-alpha-maltosyl-alpha-maltotrioside
  • Maltose
  • starch synthase II
  • Starch Synthase
  • Glucose