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

Abstract

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.