Resolution of dihydroxyeicosanoates and of dihydroxyeicosatrienoates by chiral phase chromatography

Anal Biochem. 1992 Dec;207(2):236-40. doi: 10.1016/0003-2697(92)90006-s.

Abstract

A chromatographic method is described for the direct enantiomeric characterization of 5,6-, 8,9-, 11,12-, and 14,15-vic-dihydroxyeicosatrienoic acids (DHETs), metabolites of the cytochrome P-450 arachidonate epoxygenase pathway, and of their corresponding saturated vic-dihydroxyeicosanoic acids. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral-phase chromatography utilizing a Chiralcel OC or OD column. This methodology will find analytical and preparative applications since it is simple and efficient and preserves, intact, the diol functionality.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / analogs & derivatives*
  • 8,11,14-Eicosatrienoic Acid / chemistry
  • 8,11,14-Eicosatrienoic Acid / isolation & purification*
  • Chromatography, High Pressure Liquid / methods
  • Cytochrome P-450 CYP2J2
  • Cytochrome P-450 Enzyme System / metabolism
  • Indicators and Reagents
  • Isomerism
  • Mass Spectrometry / methods
  • Oxygenases / metabolism

Substances

  • Indicators and Reagents
  • Cytochrome P-450 Enzyme System
  • Oxygenases
  • Cytochrome P-450 CYP2J2
  • 8,11,14-Eicosatrienoic Acid