Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: (animal); Homo sapiens
Associated disease: infectious gastroenteritis [ICD11:
1A40.Z 
];
diarrhea [ICD11:
ME05.1 , ICD11:
SA55 ];
urinary tract infections (UTI) [ICD11:
GC08 ];
septicemia [ICD11:
MA15.Y ];
meningitis [ICD11:
1D01 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 34126435Publication DOI: 10.1016/j.carres.2021.108366Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mbalaram
iiserkol.ac.in
Institutions: Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia 741246, India
Chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O74 is accomplished by a convergent [2 + 2] block synthesis strategy. The challenging rare D-Fuc3NAc has been prepared using DTBP and TIPST mediated deoxygenation reaction. Other monosaccharide synthons are prepared through rational protecting group manipulations and the stereoselective glycosylations are achieved either by the activation of thioglycoside or glycosyl trichloroacetimidate. The target tetrasaccharide is made in the form of its 2-aminoethyl glycoside to facilitate further glycoconjugate formation without affecting the anomeric stereochemistry.
O-antigen, total synthesis, D-Fuc3NAc, E.coli O74, rare sugar
Structure type: oligomer ; 853.3178 [M+Na]+
C
32H
54N
4O
21Location inside paper: Fig. 1, compound 1
Aglycon: 2-aminoethyl
Compound class: O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, optical rotation measurement, flash chromatography, HR-MS
Synthetic data: chemical
Comments, role: the tetrasaccharide repeating unit of the O-antigen from E. coli O74
NCBI Taxonomy refs (TaxIDs): 2067425
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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