Specific tritium labeling of cerebrosides at the 3-positions of erythro-sphingosine and threo-sphingosine.
Cerebrosides containing either threo- or erythro-[3-3-H]sphingosine were synthesized by a new procedure. Glucopyranosyl or galactopyranosyl ceramides were converted to their 3-keto derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone and reduced with 3-H-labeled sodium borohydride. The resulting tritiated cerebrosides, which contained erythro- and threo-sphingosines in the ratio of 84:16, were deacylated with butanol-KOH, and the erythro- and threo-psychosines were separated by silica gel column chromatography and reacylated with lignoceroyl chloride.
D000818:Animals; D001923:Brain Chemistry; D002417:Cattle; D002554:Cerebrosides / Q000138:chemical synthesis; D002855:Chromatography, Thin Layer; D005227:Fatty Acids; D005697:Galactosides; D005960:Glucosides; D007553:Isotope Labeling; D000432:Methanol; D008722:Methods; D010084:Oxidation-Reduction; D013110:Sphingosine; D014316:Tritium
D002554:Cerebrosides; D005227:Fatty Acids; D005697:Galactosides; D005960:Glucosides; D014316:Tritium; D013110:Sphingosine; D000432:Methanol