Stereospecific synthesis and mass spectrometry of 5,6-trans-epoxy-8Z,11Z,14Z-eicosatrienoic acid

Bioorg Med Chem Lett. 2005 Jun 15;15(12):3029-33. doi: 10.1016/j.bmcl.2005.04.030.

Abstract

A novel, facile synthesis of 5,6-trans-epoxyeicosatrienoic acid (5,6-trans-EET) from 5,6-trans-arachidonic acid by iodolactonization and alkaline de-iodation is described along with characterization by mass spectrometry (LC-MS, negative ions) and NMR and comparison with 5,6-cis-EET.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / analogs & derivatives*
  • 8,11,14-Eicosatrienoic Acid / chemical synthesis
  • 8,11,14-Eicosatrienoic Acid / chemistry
  • 8,11,14-Eicosatrienoic Acid / isolation & purification
  • Arachidonic Acid / metabolism
  • Chromatography, High Pressure Liquid
  • Gas Chromatography-Mass Spectrometry
  • Spectrometry, Mass, Electrospray Ionization*
  • Stereoisomerism

Substances

  • Arachidonic Acid
  • 5,6-epoxy-8,11,14-eicosatrienoic acid
  • 8,11,14-Eicosatrienoic Acid