Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H8]-analogues through a common synthetic route |
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| Authors: | Stepan G Romanov Igor V Ivanov Valery P Shevchenko Igor Yu Nagaev Alexandr A Pushkov Nikolai F Myasoedov Galina I Myagkova Hartmut Kuhn |
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| Institution: | a M.V. Lomonosov State Academy of Fine Chemical Technology, Pr. Vernadskogo 86, 119571, Moscow, Russia;b Institute of Biochemistry, University Clinics Charité, Humboldt University, Monbijoustr. 2, D-10117, Berlin, Germany;c Institute of Molecular Genetics, Kurchatov Square 2, 123182, Moscow, Russia |
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| Abstract: | Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their 5,6,8,9,11,12,14,15-3H8]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. |
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| Keywords: | Eicosanoids Photo-affinity probes Cross-coupling Azido compounds Tritium-labelled fatty acids |
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