A convenient route to mono-trans polyunsaturated free fatty acids

Journal of Chemical Research-s Pub Date : 2022-03-01 DOI:10.1177/17475198221090908

Fabrizio Vetica, A. Sansone, C. Ferreri, C. Chatgilialoglu

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引用次数: 2

Abstract

Trans unsaturated fatty acids in humans may be originated both from dietary supplementation and from an endogenous free-radical-catalyzed cis−trans isomerization of fatty acid residues in naturally occurring cis lipids. The latter process affords geometrical isomers and the polyunsaturated fatty acid mono-trans isomers were demonstrated to be connected with stress conditions in living organisms. Synthesis of mono-trans polyunsaturated fatty acid is useful for analytical and biological research, and in this case, the availability of free fatty acids is needed as well as the possibility of mg scale of the synthetic protocol. Herein, we report a simple synthetic route to mono-trans isomers of arachidonic acid, eicosapentaenoic acid, and docosahexaenoic acid, which includes thiyl radical-catalyzed isomerization reaction of polyunsaturated fatty acid methyl esters and fraction isolation of mono-trans mixture isomers followed by optimization of hydrolysis condition to free fatty acids and purification of each mono-trans polyunsaturated fatty acid. Our approach to mono-trans polyunsaturated fatty acids as free acids can reach the mg scale, thus fostering more applications to biochemical and biological studies.

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单反式多不饱和游离脂肪酸的便捷途径

人体内的反式不饱和脂肪酸可能来源于膳食补充，也可能来源于天然存在的顺式脂质中脂肪酸残基的内源性自由基催化的顺-反异构化。后一过程提供几何异构体和多不饱和脂肪酸单反式异构体被证明与生物体的应激条件有关。单反式多不饱和脂肪酸的合成对分析和生物学研究是有用的，在这种情况下，需要自由脂肪酸的可用性以及合成方案的毫克规模的可能性。本文报道了花生四烯酸、二十碳五烯酸和二十二碳六烯酸单反式异构体的简单合成路线，包括巯基自由基催化的多不饱和脂肪酸甲酯异构化反应和单反式混合物异构体的分离，然后优化水解条件以获得游离脂肪酸和纯化每种单反式多不饱和脂肪酸。我们将单反式多不饱和脂肪酸作为游离酸的方法可以达到毫克级，从而在生化和生物学研究中有更多的应用。

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来源期刊

Journal of Chemical Research-s 化学科学, 有机化学, 有机合成

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审稿时长

1 months

期刊介绍： The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.