Synthesis of 11,12‐leukotriene A4, 11S,12S‐oxido‐5Z,7E,9E,14Z‐eicosatetraenoic acid, a novel leukotriene of the 12‐lipoxy genase pathway

FEBS Letters

Seyama, Yousuke¹  Izumi, Takashi¹  Kitamura, Shigeto¹  Shimizu, Takao¹ 

[1] Department of Physiological Chemistry and Nutrition, Faculty of Medicine, University of Tokyo, Bunkyo-ku, Tokyo 113, Japan

关键词: 12-Lipoxygenase;    Leukotriene;    11;    12-Leukotriene A4;    12-Hydroperoxyicosatetraenoic acid;    LT;    leukotriene;    12-H(P)ETE;    12S-hydro(pero)xy-5Z;    8Z;    10E;    14Z-eicosatetraenoic acid;    5-H(P)ETE;    5S-hydro(pero)xy-6E;    8Z;    11Z;    14Z-eicosatetraenoic acid;    15-H(P)ETE;    15S-hydro(pero)xy-5Z;    8Z;    1 lZ;    13E-eicosatetraenoic acid;    GC-MS;    gas chromatography-mass spectrometry;    PMP;    1;    2;    2;    6;    6-pentamethylpiperidine;    SP;    straight-phase;    RP;    reversed-phase;   

DOI  :  10.1016/0014-5793(87)81485-0

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

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.

【 授权许可】

Unknown