11,12-白三烯A4（11S,12S-环氧-5Z,7E,9E,14Z-二十碳四烯酸）的合成，一种12-脂氧合酶途径的新型白三烯。

Synthesis of 11,12-leukotriene A4, 11S,12S-oxido-5Z,7E,9E,14Z-eicosatetraenoic acid, a novel leukotriene of the 12-lipoxygenase pathway.

作者信息

Kitamura S, Shimizu T, Izumi T, Seyama Y

出版信息

FEBS Lett. 1987 Mar 9;213(1):169-73. doi: 10.1016/0014-5793(87)81485-0.

Abstract

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.

摘要

通过从花生四烯酸出发的立体定向仿生途径，建立了一种简单有效的制备11,12-白三烯A4的方法。使用猪白细胞部分纯化的12-脂氧合酶合成了12S-氢过氧-5Z,8Z,10E,14Z-二十碳四烯酸。然后将该化合物的甲酯化学转化为具有共轭三烯结构的两种不稳定环氧化物。通过质子核磁共振和质谱鉴定这些化合物为11S,12S-环氧-5Z,7E,9E,14Z-二十碳四烯酸（11,12-白三烯A4）及其几何异构体。