[Synthesis of 2-acetamido-2-deoxy-6-0-(alpha-D-glucopyranosyl)-alpha-D-galactopyranose and its p-aminophenyl-alpha-glycoside]

Carbohydr Res. 1975 Mar;40(1):13-22. doi: 10.1016/s0008-6215(00)82664-6.
[Article in French]

Abstract

Benzyl 2-acetamido-3, 4-di-O-acetyl-2-deoxy-alpha-D-galactopyranoside was condensed with 2, 3, 4-tri-O-benzyl-6-O-p-nitrobenzoyl-alpha-D-glucopyranosyl bromide or with 2, 3, 4-tri-O-benzyl-6-O-p-methoxybenzoyl-alpha-D-glucopyranosyl bromide in benzene at 50 degrees in the presence of pyridine, to give benzyl 2-acetamido-3, 4-di-O-acetyl-2-deoxy-6-O-[2, 3, 4-tri-O-benzyl-6-O-p-nitro(or methoxy)benzoyl]-alpha-D galactopyranoside in excellent yield. The title disaccharide was obtained in crystalline form after deacylation and catalytic hydrogenation. It proved identical with a disaccharide isolated from Salmonella johannesburg 5.58 (40) converted by phage phi 1 (40). In order to bind this disaccharide covalently onto various proteins, p-aminophenyl 2-acetamido-2-deoxy-6-O-(alpha-D-glucopyranosyl)-alpha-D-galactopyranoside has been obtained in an analogous way, starting from p-nitrophenyl 2-acetamido-3, 4-di-O-acetyl-2-deoxy-alpha-D-galactopyranoside.

Publication types

  • English Abstract

MeSH terms

  • Binding Sites
  • Chromatography, Thin Layer
  • Disaccharides / chemical synthesis*
  • Glucosamine
  • Glucose
  • Glycosides / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Methods
  • Optical Rotation
  • Phenols
  • Protein Binding
  • Salmonella / analysis
  • Salmonella Phages
  • Spectrophotometry, Infrared

Substances

  • Disaccharides
  • Glycosides
  • Phenols
  • Glucose
  • Glucosamine