Synthesis of sphingomyelin sulfur analogue and its behavior toward sphingomyelinase.
The sulfur analogue of sphingomyelin was designed and stereoselectively synthesized from S-benzyl-N-Boc-cysteine. The introduction of the phosphoryl choline moiety was successfully achieved by our own method using 2-bromoethyl dimethyl phosphite and carbon tetrabromide followed by a trimethylamine treatment. The synthesized compound proved to be a useful substrate for monitoring the enzyme activity of sphingomyelinase by detecting the liberated thiol group with a thiol-sensitive reagent.
Hakogi
Toshikazu
T
School of Science, Kwansei Gakuin University, Gakuen, Sanda, Hyogo 669-1337, Japan.
Fujii
Shinobu
S
Morita
Michio
M
Ikeda
Kiyoshi
K
Katsumura
Shigeo
S
D001409:Bacillus cereus / Q000187:drug effects / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D013109:Sphingomyelins / Q000138:chemical synthesis* / Q000378:metabolism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000378:metabolism
D004791:Enzyme Inhibitors; D013109:Sphingomyelins; D013457:Sulfur Compounds; D013108:Sphingomyelin Phosphodiesterase