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A simple, rapid procedure for the preparation of deuterium-labelled testosterone

✍ Scribed by Simon J. Gaskell; Elizabeth M. H. Finlay

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
412 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A simple and rapid procedure for the preparation of [16,16‐^2^H~2~]‐and [16,16,17‐^2^H~3~]testosterone of high isotopic purity is described. [16,16‐^2^H~2~]DehydrOepiandrosterone is obtained by base‐catalysed exchange; reduction of the 17‐keto group using lithium aluminium hydride or lithium aluminium deuteride is followed by selective enzymic oxidation of the 3β‐hydroxy function with concomitant Δ^5^ to Δ^4^ isomerisation. The incorporation of deuterium in intermediates and products is established by gas chromatographic‐mass spectrometrie analyses of parent compounds and alkylsilyl derivatives. Deuterium labels in the 16 and 17 positions of testosterone are shown to be non‐labile under strongly acidic and basic conditions.

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