Synthesis of 5-(S)-HETE, 5-(S)-HEPE and (+)-zooxanthellactone: Three hydroxylated polyunsaturated fatty acid metabolites.
作者： Karoline Gangestad Primdahl , Yngve Stenstrøm , Trond Vidar Hansen , Anders Vik
DOI: 10.1016/J.CHEMPHYSLIP.2015.12.005
关键词: Polyunsaturated fatty acid 、 Organic chemistry 、 Arachidonic acid 、 Eicosapentaenoic acid 、 Chemistry 、 Hydroxylation 、 Biomimetic synthesis 、 Fatty acid 、 Natural product 、 Docosahexaenoic acid 、 Stereochemistry
摘要: Short and stereoselective syntheses of the two hydroxylated polyunsaturated fatty acid metabolites, namely 5-(S)-HETE 5-(S)-HEPE, are reported in 23% 30% overall yields, respectively. In addition, synthesis natural product (+)-zooxanthellactone has been achieved 19% yield. The three aforementioned compounds have conveniently prepared six steps, starting from corresponding commercially available acids arachidonic acid, eicosapentaenoic docosahexaenoic All products were using a biomimetic synthesis.
sci-hub.se 参考文章(50)
P. E. Kolattukudy, K. E. Espelie, K. A. Potter, R. W. Leid, Stimulation of equine eosinophil migration by hydroxyacid metabolites of arachidonic acid. American Journal of Pathology. ,vol. 121, pp. 361- 368 ,(1985)
M. J. Thomas, C. J. Lees, C. E. McCall, J. T. O'Flaherty, Neutrophil-aggregating activity of monohydroxyeicosatetraenoic acids. American Journal of Pathology. ,vol. 104, pp. 55- 62 ,(1981)
XIANHAI HUANG, ROBERT G ASLANIAN, None, Case studies in modern drug discovery and development : John Wiley & Sons,. ,(2012)
W.S. Powell, F Gravelle, S Gravel, Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. Journal of Biological Chemistry. ,vol. 267, pp. 19233- 19241 ,(1992) , 10.1016/S0021-9258(18)41766-8
P Borgeat, M Hamberg, B Samuelsson, Transformation of arachidonic acid and homo-gamma-linolenic acid by rabbit polymorphonuclear leukocytes. Monohydroxy acids from novel lipoxygenases. Journal of Biological Chemistry. ,vol. 251, pp. 7816- 7820 ,(1976) , 10.1016/S0021-9258(19)57008-9
W.S. Powell, S. Gravel, F. Gravelle, Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils Journal of Lipid Research. ,vol. 36, pp. 2590- 2598 ,(1995) , 10.1016/S0022-2275(20)41095-8
Joshua Rokach, Julian Adams, Richard Perry, A new general method for the synthesis of lipoxygenase products: preparation of ±5-HETE Tetrahedron Letters. ,vol. 24, pp. 5185- 5188 ,(1983) , 10.1016/S0040-4039(00)88392-6
Philip Peach, David J. Cross, Jennifer A. Kenny, Inderjit Mann, Ian Houson, Lynne Campbell, Tim Walsgrove, Martin Wills, Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones Tetrahedron. ,vol. 62, pp. 1864- 1876 ,(2006) , 10.1016/J.TET.2005.11.036
William S. Powell, Joshua Rokach, The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor. Progress in Lipid Research. ,vol. 52, pp. 651- 665 ,(2013) , 10.1016/J.PLIPRES.2013.09.001
Karoline Gangestad Primdahl, Jørn Eivind Tungen, Marius Aursnes, Trond Vidar Hansen, Anders Vik, An efficient total synthesis of leukotriene B4 Organic and Biomolecular Chemistry. ,vol. 13, pp. 5412- 5417 ,(2015) , 10.1039/C5OB00473J