Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
]
The structure was elucidated in this paperNCBI PubMed ID: 8013005Publication DOI: 10.1016/0008-6215(94)80035-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD 20892.
The synthesis of the tetra- and hexa-saccharide methyl glycosides α-D-Galp-(1→3)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-OMe (1), and α-L-Rhap-(1→3)-α-L-Rhap-(1→2)-α-D-Galp-(1→3)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-OMe (3) is described, which represent various epitopes of the O-specific polysaccharide of Shigella dysenteriae type 1. The following monosaccharide intermediates were used: 1,3-di-O-acetyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranose (6 α), methyl 2,4-di-O-benzyl-α-L-rhamnopyranoside (7), methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (8), 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (9), methyl 3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (13), methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (16), and 2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-β-D-glucopyranosyl chloride (19). A detailed analysis of the 1H and 13C NMR spectra of oligosaccharides 1 and 3 confirmed that the hexasaccharide 3 better approaches the conformation of the native polysaccharide, than either 1 or the homologous pentasaccharide 41.
NMR, synthesis, O-specific polysaccharide, Shigella dysenteriae type 1
Structure type: polymer chemical repeating unit
Location inside paper: p.190, A
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
Methods: 13C NMR, 1H NMR, NMR-2D, chemical methods, NMR-1D
Synthetic data: chemical
Comments, role: published polymerization frame was shifted for conformity with other records.
Related record ID(s): 21474, 22420, 22473, 22474
NCBI Taxonomy refs (TaxIDs): 984897Reference(s) to other database(s): GTC:G76746EO, GlycomeDB:
6223
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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