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CHEMICAL SYNTHESIS OF [ 3 H]CEREBROSIDE [ 35 S]SULFATE AND ITS IN VIVO METABOLISM IN RAT BRAIN
Author(s) -
aka Genichiro,
Kishimoto Yasuo
Publication year - 1979
Publication title -
journal of neurochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.75
H-Index - 229
eISSN - 1471-4159
pISSN - 0022-3042
DOI - 10.1111/j.1471-4159.1979.tb11701.x
Subject(s) - saponification , cerebroside , chemistry , sulfate , benzoyl chloride , metabolism , solvolysis , biochemistry , in vivo , sulfuric acid , chromatography , organic chemistry , biology , hydrolysis , microbiology and biotechnology
—Double‐labeled sulfatide containing [3‐ 3 H]lignoceric acid and [ 35 S]sulfate was synthesized and injected intracerebrally into 28‐day‐old rats. The 3 H‐labeled sulfatide was synthesized by condensing (RS)‐[3‐ 3 H]lignoceroyl chloride with lysosulfatide which had been obtained by saponification of sulfatide. The 35 S‐labeled sulfatide was synthesized by using [ 35 S]sulfuric acid for sulfating 2′, 4′, 6′‐tri‐benzoyl‐galactosyl N ‐fatty acyl, N ‐benzoyl‐3‐0‐benzoyl‐sphingosine, which had been obtained by per‐benzoylation followed by solvolysis of calf brain nonhydroxycerebrosides. The perbenzoylated [ 35 S]sul‐fatide was then subjected to mild alkaline saponification. Eight hours following the injection, the brain lipids contained various radioactive sphingolipids in addition to sulfatides. Fourteen per cent of the injected 3 H was recovered in total lipids, and 26% of this was found in sulfatide. Nonhydroxy‐ and hydroxyceramides, nonhydroxy‐ and hydroxycerebrosides, and polar lipids contained 7, 1, 8, 3, and 22 per cent of the 3 H found in total lipids, respectively. On the other hand, only 6% of the 35 S injected was recovered in total lipids; 63% of this was found in sulfatide, 5% in a mixture of seminolipid and cholesterol sulfate and 10% in a water‐soluble material.