SYNTHETIC STUDY OF IONOPHORETIC SPHINGOGLYCOLIPID

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In this research project, we have developed a new synthetic method for optically active sphingoglycolipids. glycerophospholipids, and glyceroglycolipids, employing a synthetic Synthon, chiral C4-epoxide, which were prepared from (2Z)-2-butene-1, 4-diol.By use of the method, we have synthesized a palmitoyl analogue of Gaucher spleen glucocerebroside, C16-platelet activating factor (C16-PAF), and a palmitoyl analogue of M-5 which is a biologically active glyceroglycolipid isolated from an Okinawan marine sponge.Furthermore, we have synthesized several analogues of soya-cerebroside II, a Ca^<++>-ionophoretic sphingoglycolipid isolated from soybean. In order to clarify the relationship between the ionophoretic activity of soya-cerebroside II and the stereostructure, we have next examined Ca^<++>-ionophoretic activities of the analogues using the apparatus W-08 and the human erythrocyte method, which were developed by us.As a result, it has been found that the presence of the 8Z-double bond, the 2'R-hydroxyl group, and the 4"S-hydroxyl group is necessary for soya-cerebroside II to show the Ca^<++>-ionophoretic activty.