Taxonomic group: bacteria / Chlamydiae
(Phylum: Chlamydiae)
Associated disease: pneumonia [ICD11:
CA40 
];
infection due to Chlamydia pneumoniae [ICD11:
XN9EE ]
The structure was elucidated in this paperNCBI PubMed ID: 19665108Publication DOI: 10.1016/j.carres.2009.06.015Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: P. Kosma <paul.kosma
boku.ac.at>
Institutions: Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria
In order to define binding interactions of Kdo-specific monoclonal antibodies directed against the chlamydial α-(2→8)-linked Kdo disaccharide epitope on a molecular level, modifications at the 7-position of the proximal and distal Kdo unit were investigated. The synthesis of 7-O-methyl and 7-azido-7-deoxy-7-epi-Kdo monosaccharide derivatives was achieved via an 8-O-TBS protected derivative, whereas methylation of O-7 at the proximal Kdo unit of the α-(2→8)-linked Kdo disaccharide was conveniently accomplished via a 4,5; 4',5'; 7',8'-tri-O-carbonyl-protected disaccharide intermediate. Attempted epimerization at C-5 of the inner unit of a α-(2→4)-linked Kdo disaccharide, however, resulted in formation of the corresponding 5,6-dehydro derivative, which was fully deprotected. Treatment of unprotected α-(2→8)- as well as α-(2→4)-linked Kdo disaccharides in neat acetic acid furnished the corresponding interresidue lactone derivatives. The lactones displayed limited stability under neutral conditions and were hydrolyzed at pH 7 within 3days. Access to the lactones, however, provides a means for selective derivatization of the carboxylic group located at the distal Kdo residue, which was demonstrated by methanolysis of the lactone to afford the monomethyl ester of the α-(2→8)-linked Kdo disaccharide. ELISA inhibition experiments of the ligands with two Kdo-specific monoclonal antibodies showed slightly reduced reactivity for the binding of the α-(2→8) Kdo-specific antibody S25-2, whereas the 7-O-methyl disaccharide antigen displayed high binding affinity toward the Kdo monosaccharide-specific antibody S67-27.
Lipopolysaccharide, Kdo, antibody, Chlamydia, Kdo lactone
Structure type: oligomer
Location inside paper: p.1663, 20
Contained glycoepitopes: IEDB_130650,IEDB_130658
Methods: 13C NMR, 1H NMR, TLC, chemical methods, MS
Synthetic data: chemical
Comments, role: synthetic disaccharide
NCBI Taxonomy refs (TaxIDs): 83558Reference(s) to other database(s): GTC:G79109EL, GlycomeDB:
37306
Show glycosyltransferases
There is only one chemically distinct structure:
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