Detection of D-erythro and L-threo sphingosine bases in preparative sphingosylphosphorylcholine and its N-acylated derivatives and some evidence of their different chemical configurations.
Sphingosylphosphorylcholine prepared from native sphingomyelin by the Kaller procedure was found to comprise about 70% of the L-threo (2S, 3S) isomer and 30% of the D-erythro (2S, 3R) isomer. This analytical result was obtained by gas-liquid chromatography (GLC) of trimethylsilyl derivatives of N-acetylsphingosines which were prepared by enzymatic hydrolysis of synthetic N-acetylsphingosylphosphorylcholines with Clostridium perfringens phospholipase C. Some other evidence of the different chemical configuration between the erythro and threo isomers of synthetic N-acylated sphingosylphosphorylcholines was also provided by thin layer chromatography (TLC), optical rotatory dispersion (ORD), and fast atom bombardment (FAB) mass spectrometry.
D000215:Acylation; D000818:Animals; D002794:Choline / Q000031:analogs & derivatives*; D002849:Chromatography, Gas; D006868:Hydrolysis; D008968:Molecular Conformation; D010767:Phosphorylcholine / Q000031:analogs & derivatives*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000032:analysis*; D013116:Spinal Cord / Q000032:analysis; D013237:Stereoisomerism; D013552:Swine; D010738:Type C Phospholipases
C005356:sphingosine phosphorylcholine; D010767:Phosphorylcholine; D010738:Type C Phospholipases; D002794:Choline; D013110:Sphingosine