Taxonomic group: bacteria / Chlamydiae
(Phylum: Chlamydiae)
Associated disease: infection due to Chlamydia [ICD11:
XN27H 
]
Publication DOI: 10.1177/096805199500200108Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Chemistry, University of Agriculture, Vienna, Austria
Five allyl glycosides corresponding to the 3-deoxy-D-manno-2-octulosonic acid (Kdo) containing genus-specific LPS epitope of Chlamydia were synthesized. Compounds 5 and 22 contain one carboxyl-reduced Kdo moiety linked to O-4 of the proximal Kdo unit, whereas the analogues 28, 34 and 36 each contain one β-linked Kdo-residue within the trisaccharide sequence Kdo p-(2→8)-Kdop-(2→4)-Kdop. Elaboration of the carboxyl-reduced derivatives was achieved by BF3•Et2O-catalyzed coupling of Kdo-fluoride derivatives 1 or 14 with the 7,8-O-carbonyl-derivative 2. The β-linked oligosaccharides were obtained by Helferich-glycosidation of the respective Kdo-disaccharide bromide derivatives 26 and 31. The deprotected compounds - characterized by H and 13C NMR spectroscopy - are suitable haptens for the immunochemical study of monoclonal antibodies directed against the Kdo-region of chlamydial and enterobacterial LPS.
Lipopolysaccharide, synthesis, LPS, trisaccharide, Kdo, Chlamydia, enterobacterial, analogue, carboxyl-reduced, chlamydial
Structure type: oligomer
Location inside paper: page 69, structure 28
Contained glycoepitopes: IEDB_130650,IEDB_130658
Methods: NMR
Synthetic data: chemical
Related record ID(s): 2873, 2981, 2983, 2984
NCBI Taxonomy refs (TaxIDs): 810Reference(s) to other database(s): GlycomeDB:
25835
Show glycosyltransferases
There is only one chemically distinct structure:
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