[Synthesis of 2-acetamido-2-deoxy-6-0-(alpha-D-glucopyranosyl)-alpha-D-galactopyranose and its p-aminophenyl-alpha-glycoside].
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.
D001665:Binding Sites; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000138:chemical synthesis*; D005944:Glucosamine; D005947:Glucose; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation; D010636:Phenols; D011485:Protein Binding; D012475:Salmonella / Q000032:analysis; D012483:Salmonella Phages; D013055:Spectrophotometry, Infrared
D004187:Disaccharides; D006027:Glycosides; D010636:Phenols; D005947:Glucose; D005944:Glucosamine
Synthèse du 2-acétamido-2-désoxy-6-O-(alpha-D-glucopyranosyl)-alpha-D-galactopyranose et de son p-aminophenyl-alpha-glycoside