Beta-eliminative cleavage of 3-ketocerebroside and 3-ketosphingomyelin |
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Authors: | Masao Iwamori Yoshitaka Nagai |
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Institution: | Department of Biochemistry, Tokyo Metropolitan Institute of Gerontology, 35-2, Sakae-cho, Itabashi-ku, Tokyo, Japan |
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Abstract: | 3-Ketosphingolipids derived from cerebroside and sphingomyelin were converted to a less polar compound in as weak alkali as 0.0005 M Na2CO3 in chloroform-methanol 2 : 1 (v/v). The product was identified as 2-acylamido-3-keto-1,4-octadecadiene by several spectroscopic procedures and cleavage was concluded to occur by beta-elimination. The beta-elimination occurred at above pH 11.5 in aqueous solution. At higher pH values deacylation also occurred. The influence of solvent effects on beta-elimination was studied. This reaction can be used to obtain d oligosaccharides, phosphorycholine and other hydrophilic moieties from sphingolipids. |
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