Brash Alan R, Schneider Claus, Hamberg Mats
Department of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University School of Medicine, Nashville, TN 37232, USA.
Lipids. 2012 Feb;47(2):101-16. doi: 10.1007/s11745-011-3612-7. Epub 2011 Oct 5.
Oxygenation and desaturation reactions are inherently associated with the abstraction of a hydrogen from the fatty acid substrate. Since the first published application in 1965, stereospecific placement of a labeled hydrogen isotope (deuterium or tritium) at the reacting carbons has proven a highly effective strategy for investigating the chemical mechanisms catalyzed by lipoxygenases, hemoprotein fatty acid dioxygenases including cyclooxygenases, cytochromes P450, and also the desaturases and isomerases. This review presents a synopsis of all published studies through 2010 on the synthesis and use of stereospecifically labeled fatty acids (71 references), and highlights some of the mechanistic insights gained by application of stereospecifically labeled fatty acids.
氧合和去饱和反应本质上与从脂肪酸底物中提取氢有关。自1965年首次发表应用以来,在反应碳上立体特异性地放置标记氢同位素(氘或氚)已被证明是研究脂氧合酶、包括环氧化酶在内的血红蛋白脂肪酸双加氧酶、细胞色素P450以及去饱和酶和异构酶所催化化学机制的一种非常有效的策略。本综述概述了截至2010年所有已发表的关于立体特异性标记脂肪酸的合成和应用的研究(71篇参考文献),并强调了通过应用立体特异性标记脂肪酸所获得的一些机理见解。