Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
]
The structure was elucidated in this paperNCBI PubMed ID: 16650395Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: pozsgayv
mail.nih.gov; vipo
helix.nih.gov
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, 31 Center Dr. Rm. 2A29, MSC 2423, Bethesda, MD 20892-2423, USA
Hexa- to tridecasaccharides corresponding to the O-specific polysaccharide (O-SP) of the Gram-negative bacterium Shigella dysenteriae type 1 were synthesized in solution phase. The syntheses utilized tetra-, octa-, and dodecasaccharide intermediates that represent one to three contiguous tetrasaccharide repeating units of the O-SP [Synlett2003, 743]. These compounds were glycosylated with mono-, di-, and trisaccharide trichloroacetamidates, which were synthesized in this study. The excellent stereodirecting effect of 4,6-O-benzophenone ketals in glycosylation reactions of 2-azido-2-deoxy-glucopyranosyl donors was demonstrated. The free oligosaccharides were characterized by (1)H and (13)C NMR spectroscopy and by high-resolution mass spectrometry. The oligosaccharides described herein contain the 5-(methoxycarbonyl)pentyl aglycon for eventual attachment to immunogenic carriers using a recently published protocol [Org. Lett.2005, 70, 6987].
synthesis, oligosaccharide, vaccine, Conjugation, protecting groups, antibacterial, Benzophenone ketal, Benzophenone ketal; Oligosaccharide; Protecting groups; Synthesis; Conjugation; Antibacterial; Vaccine
Structure type: polymer chemical repeating unit
Location inside paper: p.1408
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: chemical synthesis
Synthetic data: chemical
Related record ID(s): 2158, 3227, 3783, 6263, 6843, 7715, 20393, 20394, 20395, 20396, 20397, 20398, 22042, 23061, 124115, 130504
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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