Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 36084574Publication DOI: 10.1016/j.carres.2022.108654Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: B. Mukhopadhyay <mbalaram
iiserkol.ac.in>
Institutions: Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia, 741246, India
Synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O131 was accomplished through a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging alpha-glycosylation of N-acetyl neuraminic acid was achieved through activation of thioglycoside using NIS-mediated glycosylation strategy. The target tetrasaccharide in the form of its 3-aminopropyl glycoside may be used for further glycoconjugate formation without hampering the anomeric stereochemistry.
O-antigen, E.coli, total synthesis, N-acetyl neuraminic acid, stereoselective glycosylation
Structure type: oligomer ; 938.3206 [M+Na]+
C
34H
58N
3O
24Location inside paper: Fig. 1, compound (1)
Aglycon: (->1) 3-aminopropyl
Compound class: 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, TLC, chemical synthesis, glycosylation, optical rotation measurement, HR-ESI-MS, flash chromatography
Synthetic data: chemical
Comments, role: tetrasaccharide repeating unit of the O-antigen from E. coli O131
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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