A facile enzymatic synthesis of sphingosine-1-phosphate and dihydrosphingosine-1-phosphate.
A procedure is described to prepare sphingosine-1-phosphate by treatment of sphingosylphosphocholine with phospholipase D, isolated from Streptomyces chromofuscus. The phosphorylated long chain bases were purified by selective precipitation and differential extraction. Milligram quantities can be obtained in a yield of about 70%. Application of the procedure to dihydrosphingosylphosphocholine results in the synthesis of dihydrosphingosine-1-phosphate.
Department of Biochemistry, Duke University Medical Center, Durham, NC 27710.
P P
PP
Van Veldhoven
R J
RJ
Foglesong
R M
RM
Bell
D002794:Choline / Q000032:analysis; D002855:Chromatography, Thin Layer; D008246:Lysophospholipids; D009682:Magnetic Resonance Spectroscopy; D010710:Phosphates / Q000032:analysis; D010739:Phospholipase D / Q000378:metabolism*; D010740:Phospholipases / Q000378:metabolism*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013997:Time Factors
D008246:Lysophospholipids; D010710:Phosphates; C060504:dihydrosphingosine 1-phosphate; C060506:sphingosine 1-phosphate; D010740:Phospholipases; D010739:Phospholipase D; D002794:Choline; D013110:Sphingosine