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Journal of Endotoxin Research
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Synthesis of deoxy analogues of (2->8)-linked 3-deoxy-{alpha}-D-manno-oct-2-ulopyranosylonic acid (Kdo) disaccharides for binding studies with Chlamydia specific monoclonal antibodies

R. Müller

Institute of Chemistry, University of Agricultural Sciences, Muthgasse 18, A-1190 Vienna, Austria

H. Brade

Research Center Borstel, Parkallee 22, D-23845 Borstel, Germany

P. Kosma

Institute of Chemistry, University of Agricultural Sciences, Muthgasse 18, A-1190 Vienna, Austria

Deoxy analogues of the Chlamydia-specific, {alpha}-(2->8)-linked Kdo disaccharide epitope modified at the pyranose ring of the terminal Kdo unit have been prepared. Utilizing the 3,5-dideoxy-D-arabino-oct-2-ulosonate bromide donor [1] and the acceptor [2] under Helferich conditions, the 5-deoxy-{alpha}-Kdo-(2->8)-{alpha}-Kdo disaccharide [3] was obtained as the minor product together with unsaturated, {alpha}-(2->8)-glycosidically and (4->8)-ether-linked derivatives [5] and [7] as the major components. Deprotection afforded the disaccharide allyl glycosides [4], [6], and [8]. Further transformation of protected intermediates by hydrogenation followed by deblocking gave the propyl glycosides [12], [14] and [17]. The compounds may be used for binding studies with Chlamydia-specific and cross-reactive, Kdospecific monoclonal antibodies.

Journal of Endotoxin Research, Vol. 4, No. 5, 347-355 (1997)
DOI: 10.1177/096805199700400506
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