Synthesis of 11,12-leukotriene A4, 11S,12S-oxido-5Z,7E,9E,14Z-eicosatetraenoic acid, a novel leukotriene of the 12-lipoxygenase pathway.
A simple and efficient method for preparing 11,12-leukotriene A4 has been established by the stereospecific biomimetic route from arachidonic acid. 12S-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid was synthesized using a partially purified 12-lipoxygenase of porcine leukocytes. The methyl ester of the compound was then chemically converted to two labile epoxides with a conjugated triene structure. These compounds were identified by proton NMR and mass spectrometry to be 11S,12S-oxido-5Z,7E,9E,14Z-eicosatetraenoic acid (11,12-leukotriene A4) and its geometric isomer.
D019377:12-Hydroxy-5,8,10,14-eicosatetraenoic Acid; D000818:Animals; D001092:Arachidonate 12-Lipoxygenase / Q000378:metabolism*; D001091:Arachidonate Lipoxygenases / Q000378:metabolism*; D001095:Arachidonic Acids / Q000138:chemical synthesis* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D006893:Hydroxyeicosatetraenoic Acids / Q000378:metabolism; D007962:Leukocytes / Q000201:enzymology; D017572:Leukotriene A4 / Q000031:analogs & derivatives*; D015289:Leukotrienes; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013552:Swine
D001095:Arachidonic Acids; D006893:Hydroxyeicosatetraenoic Acids; D017572:Leukotriene A4; D015289:Leukotrienes; D019377:12-Hydroxy-5,8,10,14-eicosatetraenoic Acid; C021201:12-HPETE; C051889:11,12-leukotriene A4; D001091:Arachidonate Lipoxygenases; D001092:Arachidonate 12-Lipoxygenase