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A reported method for the preparation of d3-methoxime derivatives as internal standards for prostaglandin assays by gas chromatography-mass spectrometry was evaluated. Sample derivatization resulted in 1.5-86% exchange of the d3-methoxime in a series of prostaglandins. Exchange was minimal when the methoxime was on the 5-membered ring; whereas, acyclic methoximes exhibited extensive exchange. Induced strain energy due to the steric interaction of the hydroxyl group and the C13-C20 alkyl side chain with the gem-dimethoxylamine transition state is offered as an explanation for the unusual stability of PGE2. The use of 18O exchange of the carboxylic acid function is presented as an alternative for the preparation of unavailable labelled eicosanoids.
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