Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography

Terry D. Hammonds; Ian A. Blair; J. R. Falck; Jorge H. Capdevila

doi:10.1016/0003-2697(89)90598-8

Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography

Terry D. Hammonds, Ian A. Blair, J. R. Falck, Jorge H. Capdevila

Biochemistry

Research output: Contribution to journal › Article › peer-review

52 Scopus citations

Abstract

A chromatographic method is described for the direct enantiomeric characterization of all four regioisomeric epoxyeicosatrienoic acid (EET) metabolites generated by the cytochrome P450 arachidonate epoxygenase pathway. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral phase HPLC utilizing a Chiralcel OB or OD column. This methodology will find analytical and preparative applications for chiral epoxides since it is convenient and efficient and does not destroy the epoxide functionality.

Original language	English (US)
Pages (from-to)	300-303
Number of pages	4
Journal	Analytical biochemistry
Volume	182
Issue number	2
DOIs	https://doi.org/10.1016/0003-2697(89)90598-8
State	Published - Nov 1 1989

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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title = "Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography",

abstract = "A chromatographic method is described for the direct enantiomeric characterization of all four regioisomeric epoxyeicosatrienoic acid (EET) metabolites generated by the cytochrome P450 arachidonate epoxygenase pathway. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral phase HPLC utilizing a Chiralcel OB or OD column. This methodology will find analytical and preparative applications for chiral epoxides since it is convenient and efficient and does not destroy the epoxide functionality.",

author = "Hammonds, {Terry D.} and Blair, {Ian A.} and Falck, {J. R.} and Capdevila, {Jorge H.}",

note = "Funding Information: We gratefully acknowledge Dr. Alan Brash for his valuable and suggestions and Dr. Michael Henry and Dr. Steve Coates Baker Chem. Co., Phillipsburg, NJ) for allowing us to evaluate of their Chiralcel columns. This work was supported by USPHS NIHDK 38226.",

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doi = "10.1016/0003-2697(89)90598-8",

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T1 - Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography

AU - Hammonds, Terry D.

AU - Blair, Ian A.

AU - Falck, J. R.

AU - Capdevila, Jorge H.

N1 - Funding Information: We gratefully acknowledge Dr. Alan Brash for his valuable and suggestions and Dr. Michael Henry and Dr. Steve Coates Baker Chem. Co., Phillipsburg, NJ) for allowing us to evaluate of their Chiralcel columns. This work was supported by USPHS NIHDK 38226.

PY - 1989/11/1

Y1 - 1989/11/1

N2 - A chromatographic method is described for the direct enantiomeric characterization of all four regioisomeric epoxyeicosatrienoic acid (EET) metabolites generated by the cytochrome P450 arachidonate epoxygenase pathway. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral phase HPLC utilizing a Chiralcel OB or OD column. This methodology will find analytical and preparative applications for chiral epoxides since it is convenient and efficient and does not destroy the epoxide functionality.

AB - A chromatographic method is described for the direct enantiomeric characterization of all four regioisomeric epoxyeicosatrienoic acid (EET) metabolites generated by the cytochrome P450 arachidonate epoxygenase pathway. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral phase HPLC utilizing a Chiralcel OB or OD column. This methodology will find analytical and preparative applications for chiral epoxides since it is convenient and efficient and does not destroy the epoxide functionality.

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Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography

Abstract

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