Stereoselectivity of the 4-hydroxylation of debrisoquine in man, detected by gas chromatography/mass spectrometry1
- 15 January 1988
- journal article
- research article
- Published by Wiley in Journal of Mass Spectrometry
- Vol. 15 (2), 63-66
- https://doi.org/10.1002/bms.1200150202
Abstract
A stable isotope assay for the quantification of debrisoquine (1) and its major urinary metabolite 4‐hydroxydebrisoquine (2) is described. The method consists of extractive derivatization of 1 and 2 by use of 1,3‐diketones, chiral derivatization of the 4‐hydroxy group of 2, and gas chromatography/negative ion chemical ionization mass spectrometry in the presence of deuterated analogues of 1 and 2. In comparison with synthetic R‐(−)‐2 and S‐(+)−2 it is shown that in vivo benzylic 4‐hydroxylation of 1 is highly stereoselective, leading predominantly to S‐(+)‐4‐hydroxydebrisoquine (enantiomeric excess ⩾90%).This publication has 16 references indexed in Scilit:
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