Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1016/j.tetlet.2008.07.089Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: ghoshrina
yahoo.com; R. Ghosh <ghosh_rina
hotmail.com>
Institutions: Department of Chemistry, Jadavpur University, Kolkata 700 032, India, Department of Chemistry, University College of Science, Kolkata 700 009, India
NIS/TfOH mediated glycosidation of methyl 3,4,6-tri-O-benzyl-α-d-mannopyranoside with phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-d-mannopyranoside furnished the corresponding disaccharide derivative in excellent yield and α-selectivity. Zémplen deacetylation of the same followed by reaction with BSP/Tf2O-preactivated phenyl 4,6-O-benzylidene-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside generated methyl 4,6-O-benzylidene-2,3-di-O-benzyl-β-d-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-d-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-d-mannopyranoside in very good yield and excellent β-selectivity. Pd/C catalyzed hydrogenation of the latter finally afforded the repeating trisaccharide of Escherichia coli 8 O-antigen as its methyl glycoside.
O-antigen, trisaccharide, Escherichia coli, cell wall polysaccharide, b-mannoside, Escherichia coli 8
Structure type: oligomer
Location inside paper: p. 5848, scheme 1, 11
Trivial name: trisaccharide repeatig unit
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, glycosylation
Synthetic data: chemical
NCBI Taxonomy refs (TaxIDs): 1010796Reference(s) to other database(s): GlycomeDB:
5261
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error