[Synthesis of the T-antigen trisaccharide O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1 to 6)-D-galactopyranose and O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galacopyranosyl)-(1 to 6)-D-glucopyranose and their binding to proteins].
The synthesis of the trisaccharides O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1 to 6)-D-galactopyranose (15) and O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1 to 6)-D-glucopyranose (27) is described and the synthesis of alpha-D-glycosides by reaction of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranosyl chloride with highly reactive hydroxyl groups is discussed. The trisaccharide 27 was coupled with serum albumin by formation of an imine intermediate and reduced to an amine, to yield a synthetic T-antigen. A similar coupling of 15 was unsuccessful.
D000954:Antigens, Surface; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011485:Protein Binding; D012709:Serum Albumin; D013329:Structure-Activity Relationship
D000954:Antigens, Surface; D007202:Indicators and Reagents; D009844:Oligosaccharides; D012709:Serum Albumin
Synthese der t-antigenen trisaccharide O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 to 6)-D-galactopyranose und O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 to 6)-D-glucopyranose und deren anknüpfung an proteine.