PREPARATION OF A NATURALLY-OCCURRING D-ERYTHRO-(2S,3R)-SPHINGOSYLPHOSPHOCHOLINE USING SHEWANELLA-ALGA NS-589

Sphingosylphosphocholine, an N-deacylated derivative of sphingomyelin, has been found to be involved in many cellular events. This paper des cribes a new method for preparation of a D-erythro-sphingosylphosphoch oline, which is naturally occurring but difficult to prepare by chemic al methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin nas found t o be efficiently converted by sphingomyelin deacylase to sphingosylpho sphocholine. Sphingosylphosphocholine was purified with a high yield f rom the culture supernatant and identified to be a D-erythro-(2S,3R)-i somer containing d18:1 sphingenine as a long-chain base by fast atom b ombardment mass spectrometry and NMR analyses.