Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
NCBI PubMed ID: 19278208Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: laurence.mulard
pasteur.fr
Institutions: Institut Pasteur, Unite de Chimie des Biomolecules (URA CNRS 2128), 28 rue du Dr Roux, F-75015 Paris, France
Six tri- to hexasaccharide fragments of the {2)-[α-D-Glcp-(1→3)]-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-[Ac→2]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→}(n) polymer ([(E)AB(Ac)CD](n)) were synthesized as their propyl glycosides. All targets share the (E)AB sequence. Following a thorough investigation on the use of N-trichloroacetylglucosamine- versus N-acetylglucosamine-containing tri- and tetrasaccharide acceptors, the successful strategy was based on an efficient combination of the trichloroacetimidate chemistry, a trichloroacetyl used as permanent N-protection, and an allyl aglycon as temporary and/or permanent anomeric protection of selected building blocks. Use of an EAB intermediate orthogonally protected at 2(A) provided both the trisaccharide target and acceptor 12, the condensation of which with a chain terminator D followed by full deprotection, gave tetrasaccharide D(E)AB. Alternatively, stepwise glycosylation of 12 with a D donor compatible with a selective deblocking at position 3(D) and a 2-O-acetyl C donor following exposure of OH-3(D) led to a pentasaccharide, which was partially and fully deprotected into free (Ac)CD(E)AB and CD(E)AB, respectively. Furthermore, chain elongation of the common D(E)AB acceptor with a 2(B)-O-levulinoyl rhamnobiose donor BC and subsequent partial or total deprotection of the resulting hexasaccharide provided B(Ac)CD(E)AB and BCD(E)AB, respectively. All of the synthesized oligosaccharides are parts of the O-antigen of Shigella flexneri 3a, a prevalent serotype. Moreover, the non-O-acetylated fragments are also parts of the S. flexneri serotype X O-antigen
synthesis, hexasaccharide, O-antigen, trisaccharide, Shigella flexneri, acceptor
Structure type: polymer chemical repeating unit
Location inside paper: p.2652, fig.1 (II)
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,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_158539,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, ESI-TOF-MS
Synthetic data: chemical
Related record ID(s): 23515, 23523, 23657, 23912, 23965, 23966, 23967, 23968, 23969, 23970, 23971, 23972
NCBI Taxonomy refs (TaxIDs): 623Reference(s) to other database(s): GTC:G25789RV, GlycomeDB:
33490
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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