Synthesis of C-8 Deuterated Glycosides of 3-Deoxy-D-manno-oct-2-ulosonic Acid (Kdo) Related to Chlamydial Lipopolysaccharides |
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Authors: | Paul Kosma Martina Strobl Andreas Hofinger Jens Ø. Duus Bent O. Petersen Klaus Bock Helmut Brade |
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Affiliation: | Institut für Chemie, Universit?t für Bodenkultur, A-1190 Wien, Austria, AT Department of Chemistry, Carlsberg Laboratory, DK-2500 Valby, Denmark, DK Forschungszentrum Borstel, Institut für Medizin und Biowissenschaften, D-23845 Borstel, BRD, DE
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Abstract: | Summary. Methyl glycosides of Kdo and a (2→8)-linked Kdo disaccharide were prepared which contain a deuterium label at C-8 of the reducing unit. The label was introduced in fair diastereoselectivity upon reduction of an aldehyde group using a chiral borane complex derived from N-benzyloxycarbonyl-(S)-proline which produced the 8-(S)-deuterated derivative as the major isomer. Further coupling with a Kdo bromide gave the α-(2→8)-linked disaccharide in good yield. The deprotected disaccharide serves as a model for NMR spectroscopic studies on the side chain conformation of a carbohydrate epitope from the bacterial pathogen Chlamydia. Received September 17, 2001. Accepted October 17, 2001 |
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Keywords: | . Carbohydrate Reduction Kdo Deuterium labeling Chlamydia. |
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