Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside

Abstract

An improved procedure for the conversion of cerebroside to ceramide and sphingosine has been devised, consisting of periodate opening of the glycosidic ring, reduction with NaBH4, and hydrolysis under very mild acid conditions to ceramide. The over-all yield is excellent and only the erythro isomer results. Alkaline hydrolysis of ceramide gives erythro-sphingosine in good yield. Application of this procedure to Gaucher cerebroside has shown it to contain the “normal” erythro-sphingosine.