Synthesis of acyl-CoA thioesters

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Abstract
An improved synthesis of fatty acyl coenzyme A has been developed that permits the synthesis of highly radioactive fatty acyl coenzyme A derivatives and thus can be used for the synthesis of high specific activity photoaffinity labels. Conditions were developed to solubilize the coenzyme A in anhydrous solvent for the acylation. The complete activation of fatty acid to the imidazolide is described and the acylation of the coenzyme A under anhydrous conditions was shown to result in the conversion of the fatty acid to the fatty acyl coenzyme A derivative. The synthetic product was shown by its chemical and biochemical reactivity to be the pure thioester of coenzyme A. The purification of the fatty acyl coenzyme A by reverse-phase chromatography is described. The yield of pure fatty acyl coenzyme A was essentially quantitative.Key words: acyl coenzyme A, N,N′-carbonyldiimidazole, high pressure liquid chromatography, imidazolide, synthesis.