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首页> 外文期刊>Journal of Lipid Research >Base- and acid-catalyzed interconversions of O-acyl- and N-acyl-ethanolamines: a cautionary note for lipid analyses.
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Base- and acid-catalyzed interconversions of O-acyl- and N-acyl-ethanolamines: a cautionary note for lipid analyses.

机译：碱和酸催化的O-酰基和N-酰基乙醇胺的相互转化：脂质分析的注意事项。

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摘要

The isolation and quantification of ethanolamine containing lipids from animal tissues may expose neutral lipid extracts to acidic or basic conditions during chromatographic separations or derivatization chemistry. While investigating the acid- and base-catalyzed production of anandamide in chromatographic fractions of rat brain extracts not containing anandamide, we observed that O,N-acyl migrations are facile. O,N-acyl migrations are well documented in synthetic organic chemistry literature, but are not well described or recognized with regard to methods in lipid isolation or lipid enzyme studies. We report here the synthesis and characterization of O- and N-acyl (palmitoyl- or arachidonoyl-)ethanolamines. Their rearrangements in base and acid are quantified by liquid chromatography;-electrospray ionization mass spectrometry. The rearrangements proceed through a cyclic intermediate that is also formed during chemical reactions commonly used for derivatization of acylethanolamines for gas chromatography-mass spectrometry.The isolation and characterization of N- or O-acylethanolamines and their enzymatic formation requires awareness and consideration of the proclivity of these compounds to chemically rearrange.
机译：从动物组织中分离和定量包含乙醇胺的脂质可能会在色谱分离或衍生化学过程中使中性脂质提取物暴露于酸性或碱性条件下。在调查不包含anandamide的大鼠脑提取物的色谱馏分中酸和碱催化的anandamide生成时，我们观察到O，N-酰基迁移很容易。 O，N-酰基迁移在合成有机化学文献中有充分的文献记载，但是关于脂质分离或脂质酶研究的方法并未得到充分描述或认可。我们在这里报告O-和N-酰基（棕榈酰基或花生四烯酰基）乙醇胺的合成和表征。它们在碱和酸中的重排通过液相色谱法;电喷雾电离质谱法定量。重排通过环状中间体进行，该中间体也在气相色谱-质谱法中通常用于酰基乙醇胺衍生化的化学反应期间形成.N-或O-酰基乙醇胺的分离和表征及其酶促形成需要认识和考虑这些化合物会进行化学重排。

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