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Synthesis of 11,12‐leukotriene A 4 , 11 S ,12 S ‐oxido‐5 Z ,7 E ,9 E ,14 Z ‐eicosatetraenoic acid, a novel leukotriene of the 12‐lipoxy genase pathway
Author(s) -
Kitamura Shigeto,
Shimizu Takao,
Izumi Takashi,
Seyama Yousuke
Publication year - 1987
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(87)81485-0
Subject(s) - stereospecificity , leukotriene , chemistry , arachidonic acid , lipoxygenase , leukotriene c4 , stereochemistry , leukotriene b4 , conjugated system , mass spectrometry , medicinal chemistry , organic chemistry , catalysis , chromatography , enzyme , asthma , inflammation , polymer , medicine
A simple and efficient method for preparing 11,12‐leukotriene A 4 has been established by the stereospecific biomimetic route from arachidonic acid. 12 S ‐Hydroperoxy‐5 Z ,8 Z ,10 E ,14 Z ‐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 11 S ,12 S ‐oxido‐5 Z ,7 E ,9 E ,14 Z ‐eicosatetraenoic acid (11,12‐leukotriene A 4 ) and its geometric isomer.