20 Re型リポ多糖の全合成(口頭発表の部)

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Lipopolysaccharide (LPS) is a glycoconjugate located at the so-called outer membrane of Gram-negative bacterial cell surface and exhibits multiple and potent biological activities including both toxic and beneficial ones. LPS is generally composed of a polysaccharide portion and an acylated glucosamine disaccharide termed lipid A which is responsible for the biological activities of LPS. Re lipopolysaccharide (Re LPS) from E. coli Re mutant is one of the structurally most simple LPS found on living bacterial cell surface, being composed of only two moles of 3-deoxy-D-manno-2-octurosonic acid (Kdo) and lipid A. For precise investigation of effects of the additional Kdo residue(s) on the bioactivities and conformation, Re LPS has been successfully synthesized for the first time. The synthesis started from D-mannose and D-glucosamine which were converted into appropriately protected Kdo and lipid A components, respectively. The desired tetrasaccharide backbone consisting of Kdo-disaccharide and lipid A was constructed by stepwise condensations of these saccharide building blocks under elaborated efficient conditions and functional group manipulations in 0.9% total yield for 23 steps followed by efficient purification by liquid-liquid partition column chromatography. The synthetic preparation was identical in all respects with a natural counterpart. By employing the same synthetic strategy, several partial structures of Re LPS were also synthesized for precise functional studies. Biological activities as well as conformational studies by NMR will also be discussed in comparison with lipid A.
天然有機化合物討論会の論文
2000-10-01

20 Re型リポ多糖の全合成(口頭発表の部)

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