The disaccharide 2-(p-aminophenyl)ethyl 4-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2,3-diacetamido-2 ,3-dideoxy-α-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-β-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-α-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.
Bordetella pertussis, vaccine, glycoconjugate
NCBI PubMed ID: 10945674Publication DOI: 10.1016/s0008-6215(99)00318-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: thomas.norberg@kemi.slu.se
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, PO Box 7015, S-750 07 Uppsala, Sweden
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