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 flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 25569152Publication DOI: 10.1039/c4cc08805kJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: laurence.mulard
pasteur.fr
Institutions: Université de Toulouse, INSA, UPS, INP, LISBP, 135 Avenue de Rangueil, F-31077 Toulouse, France, CNRS, UMR5504, F-31400 Toulouse, France, Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France, CNRS UMR 3523, Institut Pasteur, F-75015 Paris, France, INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, F-31400 Toulouse, France
The powerful chemo-enzymatic synthesis of the pentadecasaccharide hapten involved in the first synthetic carbohydrate-based vaccine candidate against endemic shigellosis is reported. The high yielding site-selective α-D-glucosylation of a lightly protected disaccharide by an engineered transglucosylase-sucrose system gave a trisaccharide, which was chemically elongated by an efficient [5+5] process.
synthesis, oligosaccharide, Shigella flexneri, vaccine
Structure type: polymer chemical repeating unit ; 2493.9602 [M+Na]+, n=3
C
98H
166N
4O
67Location inside paper: p.2581, fig.1(b), p.2583, scheme 1, compound 1
Aglycon: 2-aminoethyl
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130687,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135806,IEDB_135807,IEDB_135808,IEDB_135809,IEDB_135813,IEDB_135817,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, HPLC, UV, glycosylation, acetylation, RP-HPLC, ESI-TOF-MS, enzymatic glucosylation
Synthetic data: chemical and enzymatic
Comments, role: Synthetic the pentadecasaccharide hapten (1) as a vaccine candidate against endemic shigellosis.
Related record ID(s): 30665
NCBI Taxonomy refs (TaxIDs): 42897Reference(s) to other database(s): GTC:G13476UX
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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