Journal of Lipid Research, Vol 26, 1002-1008, Copyright © 1985 by Lipid Research, Inc.
Synthesis and stereochemical determination of diunsaturated valproic acid analogs including its major diunsaturated metabolite
A Acheampong and FS Abbott
Valproic acid, an antiepileptic drug, is transformed into diunsaturated
metabolites in humans. Synthesis of the geometric isomers of 2-(1'-
propenyl)-2-pentenoic acid and 2-(1'-propenyl)-3-pentenoic acid was
attempted using known procedures. The final product, a mixture of isomers,
was converted into tert-butyldimethylsilyl or ethyl derivatives. Capillary
gas-liquid chromatography-mass spectrometry analysis of the derivatives
showed at least three isomeric dienoic acids from synthesized products.
Argentation thin-layer chromatography was effective in resolving the
isomeric mixture into a single isomer or mixture of two isomers. Thin-layer
chromatography and gas-liquid chromatography retention data, photochemical
isomerization studies, and nuclear magnetic resonance spectrometry were
used to characterize the dienoic acids. By comparison of the retention
times of the diunsaturated metabolites with synthesized reference
compounds, the structure assigned to the major diunsaturated metabolite is
2-[(E)-1'- propenyl](E)-2-pentenoic acid.
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