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Journal of Endotoxin Research
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Synthesis of neoglycoproteins containing Kdo epitopes specific for Chlamydophila psittaci lipopolysaccharide

Paul Kosma

Department of Chemistry, University of Agricultural Sciences, Austria, pkosma{at}edv2.boku.ac.at

Andreas Reiter

Department of Chemistry, University of Agricultural Sciences, Austria

Andreas Hofinger

Department of Chemistry, University of Agricultural Sciences, Austria

Lore Brade

Research Center Borstel, Borstel, Germany

Helmut Brade

Research Center Borstel, Borstel, Germany

The oligosaccharides {alpha}-Kdo p-(2->8)-{alpha}-Kdop-(2->6)-ß-D-GlcpNAc-(1->OAll) 4, {alpha}-Kdop-(2->4)-{alpha}-Kdop-(2->4)-{alpha}-Kdo p-(2->6)-ß-D-GlcpNAc-(1->OAll) 10, and the branched Kdo tetrasaccharide {alpha}-Kdop-(2->4)-[{alpha}-Kdop-(2->8)]-{alpha}-Kdo p-(2->4)-{alpha}-Kdop-(2->OAll) 21 have been prepared using en bloc transfer of Kdo oligosaccharide bromide donors to protected mono- or disaccharide acceptors. Radical addition of cysteamine to the anomeric allyl glycosides afforded good yields of the corresponding 3-(2-aminoethylthio)propyl glycosides 5, 11 and 22. The spacer ligands were activated with thiophosgene and reacted with bovine serum albumin to give the neoglycoconjugates 6, 12 and 23 which were used to prepare solid-phase antigens in enzyme immuno-assays for the characterization of monoclonal antibodies against chlamydial LPS. The data showed that the (2->8)-linked Kdo disaccharide and the (2->8)-(2->4)-linked Kdo trisaccharide portion of the neoglycoconjugate 23 were not available for binding of antibodies which recognize these structures as di- and trisaccharide, respectively.

Journal of Endotoxin Research, Vol. 6, No. 1, 57-69 (2000)
DOI: 10.1177/09680519000060010801
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