Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
dysentery [ICD11:
SA56 ];
infection due to Escherichia coli [ICD11:
XN6P4 ];
infection due to Shigella dysenteriae [ICD11:
XN285 ]
NCBI PubMed ID: 21181263Publication DOI: 10.1007/s10719-010-9317-yJournal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: akmisra69
gmail.com
Institutions: Molecular Medicine Division, Bose Institute, P-1/12, C. I. T. Scheme VII M, Kolkata, 700054, India
A convenient synthetic strategy of the common acidic pentasaccharide repeating unit corresponding to the O-antigen of enterotoxigenic E. coli O168 and Shigella dysenteriae type 4 has been successfully developed. A stereoselective [2 + 3] block glycosylation method has been exploited to get the target pentasaccharide derivative. Most of the synthetic intermediates were solid and prepared in high yields from commercially available reducing sugars following a series of protection-deprotection reactions. A α-D-mannose moiety has been used as the source of α-D-glucosamine moiety. A late-stage TEMPO mediated selective oxidation reaction finally resulted in the pentasaccharide containing a glucuronic acid unit.
lipopolysaccharides, Escherichia coli, antigens, Shigella dysenteriae, Glycosylations
Structure type: polymer chemical repeating unit
Location inside paper: p.12, fig.1
Trivial name: DPS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136045,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,SB_74,SB_85,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, glycosylation, TEMPO oxidation
Synthetic data: chemical
Comments, role: revised structure in ID 22716
Related record ID(s): 21481, 23210, 25656, 26635
NCBI Taxonomy refs (TaxIDs): 2603287,
1633494Reference(s) to other database(s): GTC:G69278UM, GlycomeDB:
34667
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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