Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

A Wittig reaction employing Li(CD₃)₂CP(C ₆H₅)₃ was used to prepare d₆- farnesol and d₆-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d₅ was used to prepare the unnatural isoprenoid analogues d₅-anilinogeraniol and d₅-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis. Deuterated isoprenols d₆-farnesol, d₆-geranylgeraniol, d₅- anilinogeraniol, d₅-anilinofarnesol and their corresponding diphosphates and cysteine thioethers were synthesized. These compounds are useful as stable-isotope labeled standards for quantitative mass spectrometric analysis.