Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 36087527Publication DOI: 10.1016/j.carres.2022.108668Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: K. Misra <akmisra69
gmail.com>
Institutions: Bose Institute, Division of Molecular Medicine, Block EN-80, Sector-V, Salt Lake, Kolkata, 700091, India
A concise synthetic strategy have been developed for the synthesis of the sialic acid-containing tetrasaccharide repeating unit of the cell wall O-antigen of Escherichia coli (E. coli) O131 strain using regio- and stereoselective (2→6)-α-glycosylations of judiciously protected sialic acid thioglycoside derivatives. Perchloric acid supported over silica (HClO4-SiO2) in combination with N-iodosuccinimide (NIS) has been used in the stereoselective activation of thioglycoside derivatives as well as used as a solid acid for the functional group modifications. Appropriate stereoselectivity was achieved in the glycosylation steps involved in the synthetic strategy.
synthesis, oligosaccharide, polysaccharide, O-antigen, sialic acid, glycosylation, E.coli
Structure type: oligomer
Location inside paper: Fig. 1, scheme 2, structure 1
Aglycon: p-methoxyphenyl
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_149174,IEDB_153201,IEDB_156493,IEDB_158551,IEDB_190606,SB_126,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_7,SB_8,SB_84,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, glycosylation, optical rotation measurement, HR-ESI-MS
Synthetic data: chemical
Comments, role: tetrasaccharide repeating unit of the O-antigen of E. coli O131
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error