The synthesis of alpha and beta-(1 less than 2) and-(1 less than 3)-linked glucopyranose disaccharides and their protein conjugates.
2,3,4-Tri-O-benzyl-6-O-(N-phenylcarbamoyl)-1-O-tosyl-D-glucopyranose and 3,4,6-tri-O-benzyl-2-O-p-nitrobenzoyl-1-O-tosyl-D-glucopyranose were allowed to react with partially blocked 2-[4-p-toluenesulfonamido) phenyl]ethyl alpha- and beta-D-glucopyranosides. Disaccharides having the structure alpha-D-Glcp-(1 goes to 2)-alpha-D-Glcp, alpha-D-Glcp-(1 goes to 3)-alpha-D-Glcp, beta-D-Glcp-(1 goes to 2)-beta-D-Glcp, and beta-D-Glcp-(1 goes to 3)-alpha-D-Glcp were synthesized. The oligosaccharides were debenzylated with sodium in liquid ammonia to give disaccharides having a free primary aromatic amino group, which were converted into isothiocyanate derivatives and then coupled to various proteins to give the corresponding conjugates.
D000818:Animals; D002236:Carbohydrate Conformation; D002417:Cattle; D004187:Disaccharides / Q000138:chemical synthesis*; D006433:Hemocyanins; D008974:Mollusca; D011107:Polylysine; D011485:Protein Binding; D012710:Serum Albumin, Bovine; D013329:Structure-Activity Relationship
D004187:Disaccharides; D011107:Polylysine; D012710:Serum Albumin, Bovine; D006433:Hemocyanins