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-beta-D-mannopyranoside.
The synthesis is described of p-nitrophenyl 2-acetamido-3-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta -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-beta-D-mannopyranosyl unit.
Classon
B
B
Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.
Garegg
P J
PJ
Oscarson
S
S
Tidén
A K
AK
D000942:Antigens, Bacterial / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000276:immunology*; D006193:Haemophilus influenzae / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D008766:Methylmannosides / Q000138:chemical synthesis* / Q000276:immunology; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000737:chemistry / Q000276:immunology
D000942:Antigens, Bacterial; D004187:Disaccharides; D008766:Methylmannosides; D011135:Polysaccharides, Bacterial; C073378:methyl 2-acetamido-2-deoxy-beta-D-mannopyranoside