31 細菌内毒素の活性部位リピドAの構造と合成

概要

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The lipophilic portion of bacterial lipopolysaccharide(LPS) is designated lipid A which is known to be responsible for most of the endotoxic activities of LPS. In the course of our synthetic study, we found that synthetic acyl disaccharide phosphates (4) corresponding to the proposed structure of lipid A showed certainly some of its typical biological activities. However, their potencies were significantly lower than those of natural samples. This prompted us to reinvestigate the chemical structure of natural lipid A. Thus, a homogeneous main component of E. coli, Re lipid A was isolated after chemical modification and its structure was elucidated as shown in 1 by combination of chemical method and the 2D-NMR technique. This was the first exact evidence for the acylation positions of the disaccharide backbone in the natural lipid A. The hitherto accepted structure (3) must be now revised. Synthesis of an acyl disaccharide diphosphate (2) based on our new structure is also being investigated.
天然有機化合物討論会の論文
1983-09-15