Taxonomic group: bacteria / Chlamydiae
(Phylum: Chlamydiae)
Associated disease: infection due to Chlamydia [ICD11:
XN27H 
]
NCBI PubMed ID: 17007824Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: paul.kosma
boku.ac.at
Institutions: Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
On the basis of high-resolution crystal structures of the antigen binding fragment of the chlamydia-specific monoclonal antibody S25-2 in complex with the trisaccharide α-Kdop-(2→8)-α-Kdop-(2→4)-α-Kdop and part structures thereof, seven modified α-Kdop-(2→8)-α-Kdop disaccharide derivatives were synthesized starting from the protected disaccharide allyl ketoside 1. Hydroboration and subsequent oxidation as well as ozonolysis, respectively, followed by Wittig-reaction for chain elongation were used to install a terminal carboxylic group on spacer entities of various chain lengths. Furthermore, addition of methyl 2-thioacetate to the allyl group furnished the corresponding thioether derivative. Standard deprotection gave the target disaccharides as simplified trisaccharide analogues, which will be used to probe the contribution of the proximal carboxylic group in the binding of chlamydia-specific di- and trisaccharide-reactive monoclonal antibodies.
Lipopolysaccharide, synthesis, trisaccharide, Kdo, antibody, epitope, spacer, chlamydial
Structure type: oligomer
Location inside paper: p.576, abstract
Aglycon: lipid A
Trivial name: Kdo-epitope
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659
Methods: 13C NMR, 1H NMR, ESI-MS, chemical methods
Synthetic data: chemical
Related record ID(s): 1765, 2449, 21721, 23401
NCBI Taxonomy refs (TaxIDs): 810Reference(s) to other database(s): GTC:G30068VP, GlycomeDB:
5771
Show glycosyltransferases
There is only one chemically distinct structure:
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