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标题：Chemical Synthesis of a Very Long-Chain Fatty Acid, Hexacosanoic Acid (C26:0), and the Ceramide Containing Hexacosanoic Acid
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作者：Yoshinori YAMAMOTO ; Toshimasa ITOH ; Keiko YAMAMOTO 等
期刊名称：Journal of Nutritional Science and Vitaminology
印刷版ISSN：0301-4800
电子版ISSN：1881-7742
出版年度：2015
卷号：61
期号：3
页码：222-227
DOI：10.3177/jnsv.61.222
出版社：Center for Academic Publications Japan
摘要：Hexacosanoic acid (C26:0) ( 1 ), a very long-chain fatty acid, is related to various diseases such as adrenoleukodystrophy (ALD), adrenomyeloneuropathy (AMN) and atherosclerosis. As the level of 1 higher than the normal is related to diseases above, hexacosanoic acid ( 1 ) and the ceramide 2 , which contains 1 , are thought to play an important role in various tissues. Hexacosanoic acid ( 1 ) is known to be a waxy solid and to be hard to dissolve in water as well as organic solvents. Due to this physical property, it is not easy to handle hexacosanoic acid ( 1 ) in a laboratory. Therefore, efficient chemical synthesis of the compounds 1 and 2 has not been reported. Here, we report a versatile synthetic method for hexacosanoic acid ( 1 ) and the ceramide 2 containing the fatty acid 1 . Synthesis of hexacosanoic acid ( 1 ) was achieved by applying the coupling of two alkyl units as a key step. Ceramide 2 was efficiently synthesized by applying the reported procedure together with hexacosanoic acid ( 1 ) synthesized here. This synthetic strategy has an advantage of getting various carbon chain length fatty acids and their ceramides by using a variety of carbon chain units. This method is also applicable for large-scale synthesis. In addition, these compounds 1 and 2 are useful for investigation of details of these compounds related to diseases such as ALD and AMN.
关键词：hexacosanoic acid;cerotic acid;ceramide;chemical synthesis;adrenoleukodystrophy