Synthesis of 2-n-(hexadecanoyl)-amino-4-nitrophenyl phosphorylcholine-hydroxide, a chromogenic substrate for assaying sphingomyelinase activity.
2-N-(Hexadecanoyl)-amino-4-nitrophenyl phosphorylcholine-hydroxide a compound resembling sphingomyelin is synthesized. It is cleaved by sphingomyelinase to the chromogenic N-acylaminonitrophenyl moiety. Phospholipase C preparations do not hydrolyze this compound. The starting material is 2-amino-4-nitrophenol which when acylated with palmitoyl chloride yields the hexadecananilide. Reaction with beta-bromoethylphosphoryldichloride gives the phosphate which is quaternized with trimethylamine to give the title compound.
D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008968:Molecular Conformation; D010743:Phospholipids / Q000138:chemical synthesis*; D010727:Phosphoric Diester Hydrolases / Q000032:analysis*; D013055:Spectrophotometry, Infrared; D013108:Sphingomyelin Phosphodiesterase / Q000032:analysis*
D010743:Phospholipids; D010727:Phosphoric Diester Hydrolases; D013108:Sphingomyelin Phosphodiesterase