Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
]
NCBI PubMed ID: 9825517Publication DOI: 10.1016/s0008-6215(98)00216-xJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: lmulard
pasteur.fr
Institutions: NIDDK, National Institutes of Health, Bethesda, MD, USA
The blockwise synthesis of methyl alpha tri- and tetrasaccharide analogs of the biochemical repeating unit of the Shigella dysenteriae type 1 O-polysaccharide is described. Modifications include deoxygenation and deoxyfluorination at position 3 of the galactopyranoside residue. Methyl 4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (8) and methyl 4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside (9) were condensed with (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride to give, after deprotection, the target trisaccharide methyl α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-3-deoxy-α-D-xylo-hexopyranoside and the corresponding fluorinated oligosaccharide. For the tetrasaccharide synthesis, the glycosyl acceptors 8 and 9 were condensed with the temporarily protected (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride. Removal of the chloroacetyl group was followed by condensation of the resulting selectively deblocked trisaccharides with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride. Reduction and deprotection then gave the free methyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-3-deoxy-α-D-xylo-hexopyra noside and the fluorinated analog.
Shigella dysenteriae type 1, deoxyfluorinated oligosaccharides, deoxygenated oligosaccharides
Structure type: polymer chemical repeating unit
Location inside paper: page 122, polysaccharide I
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137483,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Synthetic data: chemical
Comments, role: published polymerization frame was shifted for conformity with other records.
Related record ID(s): 3887, 3888, 3889, 3891
NCBI Taxonomy refs (TaxIDs): 984897Reference(s) to other database(s): GTC:G76746EO, GlycomeDB:
6223
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There is only one chemically distinct structure:
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