Synthesis of deuterium‐labelled coenzyme Q 10

Deuterium‐labelled coenzyme Q 10 ([2‐CD 3 ‐1′‐CD 2 ]coenzyme Q 10 , coenzyme Q 10 ‐d 5 ) was synthesized by condensation of 2,3‐dimethoxy‐[5‐CD 3 ]methyl‐1, 4‐hydroquinone with [1‐CD 2 ]decaprenol. Five positions were selected for deuteration as replacement at these positions allowed examination of every step of the synthesis. This examination was carried out by a combination of 1 H‐ and 13 C‐nuclear magnetic spectrometry and mass spectrometry. Further, these positions have been proved to be metabolically stable. This reagent makes simultaneous quantification of the source of coenzyme Q 10 (exogenously supplied or endogenously supplied) possible in biological samples by measurements on gas chromatography–mass spectrometry. Copyright © 2002 John Wiley & Sons, Ltd.