Synthesis of a spacer-containing disaccharide fragment of Bordetella pertussis lipopolysaccharide.
The disaccharide 2-(p-aminophenyl)ethyl 4-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-2,3-diacetamido-2 ,3-dideoxy-alpha-D-mannopyranoside uronate, which is assumed to be a partial structure of the Bordetella pertussis polysaccharide, was synthesized starting from D-glucose and D-glucosamine, respectively. The major synthetic transformations were conversion of D-glucosamine into the donor ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-beta-D-glucopyranoside and conversion of glucose, by a sequence involving 2,3-epoxide formation/opening, nucleophilic triflate displacement in the 3-position, and necessary protecting group manipulations, into the acceptor 2-(p-trifluoroacetamidophenyl)ethyl 6-O-benzyl-2,3-diazido-2,3-dideoxy-alpha-D-mannopyranoside. Coupling of the donor and acceptor units promoted by dimethyl(methylthio)sulfonium triflate followed by selective oxidation of the 6'-position and deprotection gave the target disaccharide.
Nilsson
M
M
Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala.
Norberg
T
T
D001886:Bordetella pertussis; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine; D005947:Glucose; D007202:Indicators and Reagents; D008070:Lipopolysaccharides / Q000737:chemistry*; D008958:Models, Molecular
C416839:2-(4-aminophenyl)ethyl 4-O-(2-acetamido-2-deoxyglucopyranosyl)-2,3-diacetamido-2,3-dideoxymannopyranoside uronate; D004187:Disaccharides; D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D005947:Glucose; D005944:Glucosamine