Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Klebsiella pneumoniae [ICD11:
XN741 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 17892864Journal 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 AB T6G 2G2
Described is the synthesis of the trisaccharide α-D-Manp-(1→3)-α-D-Manp-(1→3)-β-D-GlcpNAcO(CH(2))(8)N(3), the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1→3)-α-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates.
Lipopolysaccharide, synthesis, oligosaccharide, Escherichia coli, Klebsiella pneumoniae, neoglycoconjugate
Structure type: oligomer
Location inside paper: p.2819, fig.2, p.2820, scheme 3
Aglycon: (CH2)8N3
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, chemical methods
Synthetic data: chemical
Comments, role: O-chain in E.coli O8, O9a, O9 and K.pneumoniae O3, O5 linked to the core OS via this with suchlike structure trisaccharide
NCBI Taxonomy refs (TaxIDs): 573,
1010796,
1010797Reference(s) to other database(s): GTC:G97599KE, GlycomeDB:
34955
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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