The synthesis of antigenic determinants for yeast D-mannans and a linear (1to 6)-alpha-D-gluco-D-mannan, and their protein conjugates.
2-O-Benzoyl-3,4,6-tri-O-benzyl-1-O-tosyl-D-mannopyranose and 2,3,4-tri-O-benzyl-6-O-(N-phenylcarbamoyl)-1-O-tosyl-D-glucopyranose were allowed to react with partially blocked 2-[4-(ptoluensulfonamido)phenyl]ethyl alpha-D-manno- and gluco-pyranosides. Disaccharides having alpha-D-Manp-(1 to 2)-alpha-D-Manp, alpha-D-Manp-(1 to 6)-alpha-D-Glcp, alpha-D-Manp-(1 to 6)-alpha-D-Manp, and alpha-D-Glcp-(1 to 6)-alpha-D-Manp structures, and a branched trisaccharide having the structure alpha-D-Manp-(1 to 2)-[alpha-D-Manp-(1 to 6)]-alpha-D-Manp were synthesized. The oligosaccharid:s were deblocked with sodium in liquid ammonia to give glycopyranosides having a free primary aromatic amine which were converted into isothiocyanate derivatives with thio-phosgene. The functionalized oligosaccharides were then coupled to bovine serum albumin to give protein conjugates.
D055598:Chemical Phenomena; D002621:Chemistry; D000939:Epitopes; D008351:Mannans / Q000276:immunology*; D008722:Methods; D011134:Polysaccharides / Q000276:immunology*; D012441:Saccharomyces cerevisiae / Q000276:immunology; D012710:Serum Albumin, Bovine
D000939:Epitopes; D008351:Mannans; D011134:Polysaccharides; D012710:Serum Albumin, Bovine