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Efficient Synthesis of the Very‐Long‐Chain n‐3 Fatty Acids, Tetracosahexaenoic Acid (C 24 :6n‐3) and Tricosahexaenoic Acid (C 23 :6n‐3)
Author(s) -
Itoh Toshimasa,
Tomiyasu Ayako,
Yamamoto Keiko
Publication year - 2011
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-011-3541-5
Subject(s) - yield (engineering) , docosahexaenoic acid , lipidology , fatty acid , biochemistry , chemical synthesis , chemistry , polyunsaturated fatty acid , long chain , clinical chemistry , biology , stereochemistry , in vitro , polymer science , materials science , metallurgy
Tetracosahexaenoic acid (C 24 :6n‐3, THA, 3 ) is an essential biosynthetic precursor in mammals of docosahexaenoic acid (C 22 :6n‐3, DHA, 1 ), the end‐product of the metabolism of n‐3 fatty acids. THA 3 is present in commercially valuable fishes, such as flathead flounder. Tricosahexaenoic acid (C 23 :6n‐3, TrHA, 2 ), an odd‐numbered‐chain fatty acid, has been identified from marine organisms such as the dinoflagellate, Amphidinium carterae . To date, few studies have examined THA 3 and TrHA 2 due to difficulties in detecting and identifying these compounds, so their chemical and biological properties remain poorly characterized. Only one methodology for the chemical synthesis of THA 3 has been presented, and no method for the synthesis of TrHA 2 has been reported. We report here the efficient synthesis of THA 3 in four steps in 56% overall yield, and the synthesis of TrHA 2 in six steps in 48% overall yield. We also present the synthesis of Δ 2 ‐THA 4 , an intermediate of β‐oxidation of THA 3 to DHA 1 , in three steps in 73% overall yield.