Thermal conversions of trimethylsilyl peroxides of linoleic and linolenic acids

被引：13
|
作者：
Grechkin, AN
Mukhtarova, LS
Hamberg, M
机构：
[1] Russian Acad Sci, Kazan Inst Biochem & Biophys, Kazan 420111, Russia
[2] Karolinska Inst, Dept Med Biochem & Biophys, Div Physiol Chem 2, S-17177 Stockholm, Sweden
来源：
CHEMISTRY AND PHYSICS OF LIPIDS | 2005年 / 138卷 / 1-2期
基金：
俄罗斯基础研究基金会;
关键词：
fatty acid hydroperoxides; trimethylsilyl peroxides; gas chromatography-mass spectrometry; thermal reactions; mechanisms;
D O I：
10.1016/j.chemphyslip.2005.09.001
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The trimethylsilyl (TMS) peroxides/esters of the fatty acid hydroperoxides (9S, 10E, 12Z)-9-hydroperoxy- 10, 12-octadecadienoic acid (9-HPOD) and (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid (13-HPOT) were subjected to gas chromatography-mass spectrometry and products formed by thermal rearrangements were identified. The main products were decadienals and the TMS derivatives of 13-oxo-9,1 1-tridecadienoic acid, epoxyalcohols, hemiacetals, and ketodienes. Oxy radicals as well as epoxyallylic radicals served as intermediates in the formation of these compounds. The thermal TMS peroxide conversions documented provided biomimetic models for enzymatic conversions of fatty acid hydroperoxides and also offered a method to generate an array of oxylipin derivatives of value as reference compounds in GC-MS studies. (c) 2005 Elsevier Ireland Ltd. All rights reserved.
引用
收藏
页码：93 / 101
页数：9
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