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

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.

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2005-06, Vol.15 (12), p.3029-3033
Main Authors: ROY, Uzzal, STARK, Russell L, JOSHUA, Robert, BALAZY, Michael
Format: Article
Language:English
Subjects:
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
Aliphatic compounds
Analytical chemistry
Arachidonic Acid - metabolism
Chemistry
Chromatographic methods and physical methods associated with chromatography
Chromatography, High Pressure Liquid
Exact sciences and technology
Gas Chromatography-Mass Spectrometry
Organic chemistry
Other chromatographic methods
Preparations and properties
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
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Description
Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.04.030