Synthesis of an artificial antigen that corresponds to a disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d. A facile synthesis of methyl 2-acetamido-2-deoxy-β-D-mannopyranoside

Article abstract of DOI:10.1016/0008-6215(92)84161-K

The synthesis is described of p-nitrophenyl 2-acetamido-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β- D-mannopyranosiduronic acid, corresponding to the disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d, which, after conversion of the p-nitro- into a p-amino-phenyl residue, may be attached to a protein to make an artificial antigen for immunological studies. The synthesis incorporates a facile route to the 2-acetamido-2-deoxy-β-D-mannopyranosyl unit. The synthesis of p-nitrophenyl 2-acetamido-3-O- (2-acetamido-2-deoxy-β-D- glucopyranosyl) -2-deoxy -β-D-mannopyranosiduronic acid, corresponding to the disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d, is described. This acid, after conversion of the p-nitro- into a p-amino-phenyl residue, may be attached to a protein to make an artificial antigen for immunological studies. The synthesis incorporates a facile route to the 2-acetamido-2 -deoxy-β-D-mannopyranosyl unit.