Synthesis of the Disaccharides of Phenolic Glycolipid I of Mycobacterium leprae with Some Kinds of Aglycone and Their Serological Activities

概要

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The bromide of the peracetate of the non-reducing-end disaccharide of phenolic glycolipid I of Mycobacterium leprae was coupled with lauryl alcohol or 3-phenylpropanol in acetonitrile in the presence of mercury cyanide. The product was the 1:1 mixture of α-and β-1inked disaccharides. The coupling of the bromide with stearyl alcohol in nitromethane-toluene gave mainly α―linked stearyl disaccharide. The complete loss of the stereoselectivity in acetonitrile was thought to be due to the lack of neibouring group participation.The activities of these disaccharides and some other synthetic disaccharides were tested in ELISA inhibition assay and direct ELISA. No compound tested in this study showed lower activity than free disaccharide in ELISA inhibition assay. Among the tested disaccharides, the compounds with long lipophilic chain as lauryl and stearyl disaccharides showed high activity in both ELISA inhibition assay and direct ELISA. On the other hand the compounds with short chain showed only the same level of the activity as that of free disaccharide in ELISA inhibition assay. And these compounds showed no activity in direct ELISA. These results suggest that long lipophilic compounds like lauryl or stearyl alcohol should be chosen for the development of the synthetic antigen convenient for direct ELISA.
奈良大学の論文