Synthesis of a neoglycoconjugate containing a Chlamydophila psittaci-specific branched Kdo trisaccharide epitope.
The branched Kdo trisaccharide sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2-->8)-[sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2-->4)]-sodium (allyl 3-deoxy-alpha-D-manno-oct-2-ulopyranosid)onate has been prepared utilizing the regioselective glycosylation of the C-7, C-8 diol entity of a Kdo monosaccharide acceptor with a Kdo bromide donor followed by the attachment of the third Kdo unit to O-4 of the disaccharide intermediate. Deacetylation and hydrolysis of the methyl ester groups furnished the trisaccharide allyl glycoside which was converted into the corresponding 3-(2-aminoethylthio)propyl glycoside. Subsequent covalent attachment to bovine serum albumin furnished a neoglycoconjugate serving as an antigen for the induction of Chlamydophila psittaci-specific monoclonal antibodies.
Kosma
Paul
P
Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria. paul.kosma@boku.ac.at
Hofinger
Andreas
A
Müller-Loennies
Sven
S
Brade
Helmut
H
D000818:Animals; D000918:Antibody Specificity / Q000276:immunology*; D000942:Antigens, Bacterial / Q000276:immunology; D002417:Cattle; D002691:Chlamydophila psittaci / Q000276:immunology*; D000939:Epitopes / Q000276:immunology*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D018796:Immunoconjugates / Q000737:chemistry* / Q000276:immunology; D051379:Mice; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000378:metabolism; D014312:Trisaccharides / Q000737:chemistry* / Q000276:immunology* / Q000378:metabolism
D000942:Antigens, Bacterial; D000939:Epitopes; D006001:Glycoconjugates; D018796:Immunoconjugates; D014312:Trisaccharides; D012710:Serum Albumin, Bovine