Resolution of dihydroxyeicosanoates and of dihydroxyeicosatrienoates by chiral phase chromatography.
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.
Capdevila
J H
JH
Department of Medicine, Vanderbilt University Medical School, Nashville, Tennessee 37232.
Wei
S
S
Kumar
A
A
Kobayashi
J
J
Snapper
J R
JR
Zeldin
D C
DC
Bhatt
R K
RK
Falck
J R
JR
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D000090762:Cytochrome P-450 CYP2J2; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D007202:Indicators and Reagents; D007536:Isomerism; D013058:Mass Spectrometry / Q000379:methods; D010105:Oxygenases / Q000378:metabolism
D007202:Indicators and Reagents; D003577:Cytochrome P-450 Enzyme System; D010105:Oxygenases; D000090762:Cytochrome P-450 CYP2J2; D015126:8,11,14-Eicosatrienoic Acid