Journal
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
Volume 51, Issue 13-14, Pages 430-434Publisher
WILEY-BLACKWELL
DOI: 10.1002/jlcr.1558
Keywords
ent-testosterone-19,19,19-d(3); trideuterium label; ent-androsterone-19,19,19-d(3); ent-etiocholanolone-19,19,19-d(3); GABA(A) receptor modulators
Funding
- NIH [GM47969]
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19-Trideuteromethyl enantiomers of androgens namely ent-testosterone, ent-androsterone and ent-etiocholanolone were prepared by total synthesis. The isotope labeling at the C-19 angular methyl group was achieved by using deuterated methyl iodide (99.5% d(3)) for introduction of C-19 before closure of the steroid A-ring. This method yields 19,19,19-trideuterated steroids without increasing the number of steps involved in the total synthesis of ent-androgens. Analysis by mass spectrometry (MS) showed no loss of deuterium during incorporation of C-19 into ent-testosterone. The availability of the compounds will enable these ent-androgens to be distinguished by MS from their natural enantiomers in future pharmacokinetic and metabolic studies.
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