Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 1
353
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 14,15-EET from Arachidonic Acid Using Urea–Hydrogen Peroxide as the Oxidant

, , &
Pages 105-110 | Received 09 Jul 2014, Published online: 20 Oct 2014

REFERENCES

  • Chacos , N. ; Falck , J. R. ; Wixtrom , C. ; Capdevila , J. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid . Biochem. Biophys. Res. Commun. 1982 , 104 , 916 – 922 .
  • Imig , J. D. Epoxides and soluble epoxide hydrolase in cardiovascular physiology . Physiol. Rev. 2012 , 92 , 101 – 130 .
  • Node , K. ; Huo , Y. ; Ruan , X. ; Yang , B. ; Spiecker , M. ; Ley , K. ; Zeldin , D. C. ; Liao , J. K. Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids . Science 1999 , 285 , 1276 – 1279 .
  • Gross , G. J. ; Gauthier , K. M. ; Moore , J. ; Falck , J. R. ; Hammock , B. D. ; Campbell , W. B. ; Nithipatikom , K. Effects of the selective EET antagonist, 14,15-EEZE, on cardioprotection produced by exogenous or endogenous EETs in the canine heart . Am. J. Physiol. Heart Circ. Physiol. 2008 , 294 , H2838 – H2844 .
  • Iliff , J. J. ; Wang , R. ; Zeldin , D. C. ; Alkayed , N. J. Epoxyeicosanoids as mediators of neurogenic vasodilation in cerebral vessels . Am. J. Physiol. Heart Circ. Physiol. 2009 , 296 , H1352 – H1363 .
  • Wang , Y. ; Wei , X. ; Xiao , X. ; Hui , R. ; Card , J. W. ; Carey , M. A. ; Wang , D. W. ; Zeldin , D. C. Arachidonic acid epoxygenase metabolites stimulate endothelial cell growth and angiogenesis via mitogen-activated protein kinase and phosphatidylinositol 3-kinase/Akt signaling pathways . J. Pharmacol. Exp. Ther. 2005 , 314 , 522 – 532 .
  • Imig , J. D. ; Navar , L. G. ; Roman , R. J. ; Reddy , K. K. ; Falck , J. R. Actions of epoxygenase metabolites on the preglomerular vasculature . J. Am. Soc. Nephrol. 1996 , 7 , 2364 – 2370 .
  • Imig , J. D. ; Hammock , B. D. Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases. Nature Rev. Drug Discov. 2009, 8, 794–805.
  • Sudhahar , V. ; Shaw , S. ; Imig , J. D. Epoxyeicosatrienoic acid analogs and vascular function . Curr. Med. Chem. 2010 , 17 , 1181 – 1190 .
  • Falck , J. R. ; Yadagiri , P. ; Capdevila , J. Synthesis of epoxyeicosatrienoic acids and heteroatom analogs . Methods Enzymol. 1990 , 187 , 357 – 364 .
  • Corey , E. J. ; Niwa , H. ; Falck , J. R. Selective epoxidation of eicosa-cis-5,8,11,14-tetraenoic (arachidonic) acid and eicosa-cis-8,11,14-trienoic acid . J. Am. Chem. Soc. 1979 , 101 , 1586 – 1587 .
  • Rich , M. R. Conformational analysis of arachidonic and related fatty acids using molecular dynamics simulations . Biochim. Biophys. Acta 1993 , 1178 , 87 – 96 .
  • Perrier , H. ; Prasit , P. ; Wang , Z. Synthesis of a radioactive photoaffinity arachidonic acid analog . Tetrahedron Lett. 1994 , 35 , 1501 – 1502 .
  • Ryan , W. J. ; Banner , W. K. ; Wiley , J. L. ; Martin , B. R. ; Razdan , R. K. Potent anandamide analogs: The effect of changing the length and branching of the end pentyl chain . J. Med. Chem. 1997 , 40 , 3617 – 3625 .
  • Cooper , M. S. ; Heaney , H. ; Newbold , A. J. ; Sanderson , W. R. Oxidation reactions using urea–hydrogen peroxide: A safe alternative to anhydrous hydrogen peroxide . Synlett 1990 , 533 – 535 .
  • Yao , F. ; Palmer , S. L. ; Khanolkar , A. D. ; Tian , X. ; Guo , J. ; Makriyannis , A. Synthesis of 15N-, 13C-, and 2H-labeled methanandamide analogs . J. Label. Compd. Radiopharm. 2003 , 46 , 115 – 129 .
  • Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.