Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Bordetella pertussis [ICD11:
XN23B 
]
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
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
Structure type: oligomer
Location inside paper: p. 263, structure 16
Aglycon: 2-(p-aminophenyl)ethyl
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531,IEDB_2275072
Synthetic data: chemical
Comments, role: disaccharide fragment of polysaccharide
NCBI Taxonomy refs (TaxIDs): 520Reference(s) to other database(s): GTC:G48936CE
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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