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 describes a new method for preparation of a D-erythro-sphingosylphosphocholine, which is naturally occurring but difficult to prepare by chemical methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin was found to be efficiently converted by sphingomyelin deacylase to sphingosylphosphocholine. Sphingosylphosphocholine was purified with a high yield from the culture supernatant and identified to be a D-erythro-(2S,3R)-isomer containing d18:1 sphingenine as a long-chain base by fast atom bombardment mass spectrometry and NMR analyses.
Sueyoshi
N
N
Laboratory of Marine Biochemistry, Faculty of Agriculture, Kyushu, University, Fukuoka, Japan.
Izu
H
H
Ito
M
M
D000581:Amidohydrolases / Q000378:metabolism; D002855:Chromatography, Thin Layer; D006092:Gram-Negative Facultatively Anaerobic Rods / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013237:Stereoisomerism
C005356:sphingosine phosphorylcholine; D010767:Phosphorylcholine; D000581:Amidohydrolases; C109210:sphingomyelin deacylase; D013110:Sphingosine