title: Synthesis of sphingomyelin sulfur analogue and its behavior toward sphingomyelinase.
abstract: 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.
authors.affiliation: School of Science, Kwansei Gakuin University, Gakuen, Sanda, Hyogo 669-1337, Japan.
authors.forename: Toshikazu
authors.initials: T
authors.lastname: Hakogi
authors.forename: Shinobu
authors.initials: S
authors.lastname: Fujii
authors.forename: Michio
authors.initials: M
authors.lastname: Morita
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Ikeda
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: 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
chemical_list: D004791:Enzyme Inhibitors; D013109:Sphingomyelins; D013457:Sulfur Compounds; D013108:Sphingomyelin Phosphodiesterase