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 paperNCBI PubMed ID: 27308211Publication DOI: 10.1002/open.201500129Journal NLM ID: 101594811Publisher: Weinheim: Wiley-VCH
Correspondence: akmisra69
gmail.com
Institutions: Bose Institute Division of Molecular Medicine P-1/12, C.I.T. Scheme VII M Kolkata 700054 India
A convergent [3+2] block synthetic strategy was developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O11 strain in excellent yield in a minimum number of steps. Several suitably functionalized thioglycoside derivatives were used as glycosyl donors during the synthesis of the target compound. A thioglycoside was the glycosyl donor used to couple with another thioglycoside derivative in a highly stereoselective manner exploiting the difference of their reactivity profile. A combination of Niodosuccinimide (NIS) and perchloric acid supported over silica gel (HClO4-SiO2) was used as a thiophilic glycosylation activator system in all stereoselective glycosylation reactions. HClO4-SiO2 acted as a user-friendly solid acid catalyst. Yields were very good in all glycosylation steps with a high stereoselective outcome. The synthetic pentasaccharide could be coupled to an appropriate protein to furnish a glycoconjugate derivative for its use in immunochemical studies.
carbohydrates, Escherichia coli, Oligosaccharides, polysaccharides, glycosylation, glycoconjugate, stereoselectivity
Structure type: oligomer ; 944.3 [M+Na]+
C
36H
63N
3O
24Location inside paper: p.48, fig.1, p.49, scheme 2, compound 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_120354,IEDB_130648,IEDB_130701,IEDB_136045,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_152206,IEDB_152214,IEDB_174333,IEDB_885822,IEDB_983930,SB_44,SB_67,SB_72,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, MALDI-MS, chemical synthesis, chemical methods, NMR-1D, CD, glycosylations
Synthetic data: chemical
Comments, role: repeating unit of OPS of E. coli O11
NCBI Taxonomy refs (TaxIDs): 1095705
Show glycosyltransferases
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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