Add time:09/05/2019         Source:sciencedirect.com

Publisher SummaryThis chapter describes the synthesis, characterization, and analysis of dicarboxylylmono–coenzyme A esters by reversed-phase high-performance liquid chromatography (HPLC) and illustrates the application of these methods to studies of the intermediates of [U-14C]hexadecanedioylmono-CoA β-oxidation. Dicarboxylylmono–CoA esters are prepared from their corresponding acylmonochlorides, which are synthesized by treating dicarboxylic, acid with an equimolar amount of thionyl chloride in 15 ml of anhydrous boiling dioxane for 5–7 hr. Dicarboxyl-2-enoyl-CoA esters are synthesized enzymatically from the respective saturated acyl–CoA esters. 3-hydroxydicarboxylylmono–CoA esters are prepared from the corresponding 2-enoyl-CoA esters. [U-14C]hexadecanedioic acid is synthesized from [U-14C]hexadecanoic acid by incubation with a washed microsomal fraction prepared from the livers of rats treated with ciprofibrate. Preliminary experiments with unlabeled hexadecanoate, and analysis by gas chromatography/mass spectrometry of the products methylated by the addition of an excess of diazomethane, show that there is about 80% conversion of hexadecanoate to hexadecanedioate. The mass spectra of the biosynthesized hexadecanedioate and standard compound are identical. The radioactive preparation is used without further purification and converted to the corresponding mono-CoA ester by incubation.

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