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The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid |
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| Authors: | Gard Gjessing Lars-Inge Gammelster Johnsen Simen Gjelseth Antonsen Jens M J Nolse Yngve Stenstrm Trond Vidar Hansen |
| Institution: | 1.Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway; (G.G.); (S.G.A.); (J.M.J.N.);2.Section of Pharmaceutical Chemistry, Department of Pharmacy, University of Oslo, P.O. Box 1068 Blindern, NO-0316 Oslo, Norway;3.Department of Mechanical, Electronic and Chemical Engineering, Faculty of Technology, Art and Design, OsloMet, P.O. Box 4, St. Olavs Plass, NO-0130 Oslo, Norway |
| Abstract: | Monohydroxylated polyunsaturated fatty acids belonging to the oxylipin class of natural products are present in marine and terrestrial sources as well as in the human body. Due to their biological activities and role in diverse biosynthetic pathways, oxylipins biosynthesized from eicosapentaenoic acid and arachidonic acid have attracted great interest from the scientific community. One example is 3-hydroxyeicosapentaenoic acid where the absolute configuration at C-3 has only been tentatively assigned. In this paper, studies on acetate type aldol reactions that enabled the preparation of 3-(R)-hydroxyeicosapentaenoic acid (3R-HETE, 2) and its enantiomer are presented. |
| Keywords: | 3-hydroxy eicosapentaenoic acid eicosanoids Nagao– Fujita acetate aldol reaction Braun acetate aldol reaction eicosapentaenoic acid docosahexaenoic acid oxylipins 19F NMR Mosher esters analysis stereoselective synthesis |