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On the Biosynthesis of Cerebrosides Containing 2-Hydroxy Acids

MASS SPECTROMETRIC EVIDENCE FOR BIOSYNTHESIS VIA THE CERAMIDE PATHWAY

From the ¹ From the Department of Medical Chemistry, Royal Veterinary College, S-104 05 Stockholm 50, Sweden

The conversion of deuterium-labeled ceramide to cerebroside has been studied. A mixture of N-(2'-d-hydroxy[4',4',5',5'-²H₄]hexadecanoyl) d-erythro-1,3-dihydroxy-2-amino-4-trans-[4,5-²H₂]octadecene and N-(2'-d-hydroxy hexadecanoyl) d-erythro-1,3-dihydroxy-2-amino-4-trans-[3-³H₁]octadecene was incubated with mouse brain microsomes and a UDP-galactose regenerating system. Both galactosyl ceramide and glucosyl ceramide were formed. The ceramide monohexosides were analyzed by gas-liquid chromatography-mass spectrometry as the trimethylsilyl ether derivatives both as intact molecules and after degradation to ceramides. The analysis conclusively showed that both compounds had been synthesized via the ceramide pathway. A third product from the incubations was identified as free sphingosine.

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