Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 18346724Publication DOI: 10.1016/j.carres.2008.02.025Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tlowary
ualberta.ca
Institutions: Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB, Canada
Described is the synthesis of 8-azidooctyl glycoside derivatives of the Escherichia coli serotype O9a O-chain tetrasaccharide repeating unit and the terminal tetrasaccharide motif in this polysaccharide, which contains a methyl group on O-3 of the distal mannopyranose residue. The assembly of these compounds involved the sequential addition of monosaccharide residues from the reducing to the nonreducing end of the molecule using glycosyl trichloroacetimidate donors. Both compounds were initially prepared as p-methoxyphenyl glycosides, which were converted to the corresponding 8-azidooctyl derivatives at a late stage in the synthesis
Lipopolysaccharide, synthesis, oligosaccharide, Escherichia coli, neoglycoconjugate
Structure type: polymer chemical repeating unit
Location inside paper: p.1779, fig.1, 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_241100,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, MALDI-MS, chemical synthesis, glycosylation
Synthetic data: chemical
Comments, role: capped by ID 23531; published polymerization frame was shifted for conformity with other records.
Related record ID(s): 884, 7236, 10713, 20623, 23531, 23532, 23533
NCBI Taxonomy refs (TaxIDs): 1010797Reference(s) to other database(s): GTC:G54439QN, GlycomeDB:
25319
Show glycosyltransferases
There is only one chemically distinct structure:
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