Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperPublication DOI: 10.1002/open.201500164Journal NLM ID: 101594811Publisher: Weinheim: Wiley-VCH
Correspondence: akmisra69
gmail.com
Institutions: Division of Molecular Medicine, Bose Institute, Kolkata, India
Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E.?coli O139 strain. The p-methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave high yields with good stereoselectivity. A (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO)-mediated selective oxidation of the primary hydroxyl group was carried out using a biphasic reaction condition at the late stage of the synthesis. Such synthetic oligosaccharides could later be effectively conjugated with proteins to prepare glycoconjugate derivatives as vaccine candidates.
Escherichia coli, enterotoxigenic, heptasaccharide repeating unitO-polysaccharide
Structure type: oligomer ; 1272.4 [M+Na]+
C
51H
79NO
34Location inside paper: p.43, fig.1, p.44, scheme 2, compound 1
Aglycon: p-methoxyphenyl
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, MALDI-MS, chemical synthesis, chemical methods, NMR-1D, CD, glycosylations
Synthetic data: chemical
Comments, role: heptasaccharide repeating unit of OPS of E. coli O139
NCBI Taxonomy refs (TaxIDs): 2079154Reference(s) to other database(s): GTC:G18296GX
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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