91097-63-1Relevant articles and documents
First Total Syntheses of Novel Non-Enzymatic Polyunsaturated Fatty Acid Metabolites and Their Identification in Edible Oils
Pavlí?ková, Tereza,Bultel-Poncé, Valérie,Guy, Alexandre,Rocher, Amandine,Reversat, Guillaume,Vigor, Claire,Durand, Thierry,Galano, Jean-Marie,Jahn, Ullrich,Oger, Camille
, p. 10090 - 10098 (2020/07/24)
Oxidative stress (OS) is an in vivo process leading to free radical overproduction, which triggers polyunsaturated fatty acid (PUFA) peroxidation resulting in the formation of racemic non-enzymatic oxygenated metabolites. As potential biomarkers of OS, their in vivo quantification is of great interest. However, since a large number of isomeric metabolites is formed in parallel, their quantification remains difficult without primary standards. Three new PUFA-metabolites, namely 18-F3t-isoprostane (IsoP) from eicosapentaenoic acid (EPA), 20-F4t-neuroprostane (NeuroP) from docosahexaenoic acid (DHA) and 20-F3t-NeuroP from docosapentaenoic acid (DPAn-3) were synthesized by two complementary synthetic strategies. The first one relied on a racemic approach to 18(RS)-18-F3t-IsoP using an oxidative radical anion cyclization as a key step, whereas the second used an enzymatic deracemization of a bicyclo[3.3.0]octene intermediate obtained from cyclooctadiene to pursue an asymmetric synthesis. The synthesized metabolites were applied in targeted lipidomics to prove lipid peroxidation in edible oils of commercial nutraceuticals.
Synthesis of 12-KETE and its 8,9-trans-isomer
Wang,Wang, Steven S.,Rokach,Rokach, Joshua,Powell,Powell, William S.,Dekle,Dekle, Catherine,Feinmark,Feinmark, Steven J.
, p. 4051 - 4054 (2007/10/02)
The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focusses on the stable precursor dithiane 13 and its conversion to 3 and 20. Biochemical e
Inhibitors of SRS-synthesis
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, (2008/06/13)
Methyl derivatives of arachidonic acid and intermediates thereto have been synthesized. These derivatives are inhibitors of SRS-A synthesis and are useful for treating and preventing allergic reactions.