Synthesis of sphingosine-1-phosphate and dihydrosphingosine-1-phosphate.
The syntheses of D-erythro-sphingosine-1-phosphate and DL-erythro-sphinganine-1-phosphate are described starting from the commercially available D-erythro-sphingosine and DL-erythro-sphinganine. The phosphate group is introduced via phosphoramidite chemistry using bis(2-cyanoethyl)-N,N-diisopropylamino-phosphoramidite as the monophosphorylating reagent. The procedure generates the phosphorylated sphingoid bases in three steps and 32-39% overall yields.
Boumendjel
A
A
National Institutes of Health, Bethesda, MD 20892.
Miller
S P
SP
D000577:Amides / Q000737:chemistry; D008246:Lysophospholipids; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D010766:Phosphorylation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000577:Amides; D008246:Lysophospholipids; D010756:Phosphoric Acids; C060504:dihydrosphingosine 1-phosphate; C060506:sphingosine 1-phosphate; C011067:phosphoramidic acid; D013110:Sphingosine; C005682:safingol