Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery (shigellosis) [ICD11:
1A02 
, ICD11:
SA56 , ICD11:
XN7HG ];
infection due to Shigella sonnei [ICD11:
XN9M9 ]
The structure was elucidated in this paperNCBI PubMed ID: 25210812Publication DOI: 10.1021/ol502395kJournal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: laurence.mulard
pasteur.fr
Institutions: Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France, CNRS UMR3523, Institut Pasteur, 75015 Paris, France, Université Paris Descartes Sorbonne Paris Cité, Institut Pasteur, 75015 Paris, France
Shigella sonnei O-antigen features a zwitterionic disaccharide repeat encompassing two rare monosaccharides. The synthesis of the AB repeat and of trisaccharides ABA' and B'AB, which validates chain elongation at either end, is reported. All targets were synthesized using a postglycosylation oxidation strategy in combination with imidate chemistry. Precursors to residue A were obtained from l-glucose. The AAT (B) donor and acceptor were obtained from d-glucosamine. A one-step Pd(OH)2/C-mediated deprotection provided the propyl glycoside targets.
synthesis, O-antigen, repeating unit, Shigella sonnei
Structure type: oligomer ; 703.265 [M+Na]+
C
27H
44N
4O
16Na
Location inside paper: p.4894, scheme 5, compound 2
Contained glycoepitopes: IEDB_142345
Methods: 13C NMR, NMR, TLC, ESI-MS, chemical synthesis, chemical methods, glycosylation, RP-HPLC
Synthetic data: chemical
Related record ID(s): 30120, 30436, 30438
NCBI Taxonomy refs (TaxIDs): 624
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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