Methyl 4-O-(4-alpha-D-glucopyranosyloxy-4-methoxybutyl)-alpha-D-+ ++glucopyranosi de, a modified oligosaccharide for studying interactions of carbohydrates with multisite proteins

Carbohydr Res. 1984 Oct 15;133(2):247-54. doi: 10.1016/0008-6215(84)85202-7.

Abstract

Methyl 4-O-(4-alpha-D-glucopyranosyloxy-4-methoxybutyl)-alpha-D-glu copyranoside (9) was synthesised by transacetalation from methyl 2,3,6-tri-O-acetyl-4-O-(4,4-dimethoxybutyl)-alpha-D-glucopyranosid e and trimethylsilyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside followed by removal of the blocking groups. Compound 9, which is methyl alpha-maltotrioside modified by replacing the middle D-glucosyl residue with an acyclic spacer, competitively inhibits the hydrolysis of p-nitrophenyl alpha-maltotrioside by porcine alpha-amylase.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, Gas
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Methylglucosides / chemical synthesis*
  • Methylglycosides / chemical synthesis*
  • Oligosaccharides / chemical synthesis*
  • Pancreas / enzymology
  • Protein Binding
  • Proteins / metabolism*
  • Structure-Activity Relationship
  • Swine
  • alpha-Amylases / metabolism

Substances

  • Indicators and Reagents
  • Methylglucosides
  • Methylglycosides
  • Oligosaccharides
  • Proteins
  • methyl 4-O-(4 alpha-glucopyranosyloxy-4-methoxybutyl)-alpha-glucopyranoside
  • alpha-Amylases