Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
NCBI PubMed ID: 15669066Publication DOI: 10.1002/chem.200400903Publisher: Vch Verlagsgesellschaft
Correspondence: lmulard
pasteur.fr
Institutions: Unite de Chimie Organique, URA CNRS 2128, Institut Pasteur, 28 rue du Dr Roux, 75724 Paris Cedex 15, France
The blockwise synthesis of the 2-aminoethyl glycosides of a deca- and a pentadecasaccharide made of two and three repeating units, respectively, of the Shigella flexneri serotype 2a specific polysaccharide is reported. The strategy relies on trifluoromethanesulfonic acid mediated glycosylation of a pentasaccharide building block acting as a glycosyl donor and a potential glycoside acceptor. Both targets were made available in amounts large enough for their subsequent conversion into glycoconjugates. Indeed, efficient elongation of the spacer through an acetylthioacetyl moiety and subsequent conjugation onto a Pan HLA DR-binding epitope (PADRE) T-cell-universal peptide resulted in two fully synthetic neoglycopeptides, which will be evaluated as potential vaccines against S. flexneri serotype 2a infections.
carbohydrates, Shigella flexneri, antigens, glycoconjugates, vaccines, glycopeptides
Structure type: polymer chemical repeating unit
Location inside paper: p.1626
Trivial name: biological repeating unit
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, TLC, chemical methods
Synthetic data: chemical
Related record ID(s): 30171, 30172
NCBI Taxonomy refs (TaxIDs): 42897Reference(s) to other database(s): GTC:G13476UX, GlycomeDB:
25371
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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