FORMATION OF [17-2H]ANDROSTA-5,16-DIEN-3BETA-OL FROM [17,21,21,21]PREGNENOLONE BY MICROSOMAL FRACTION OF BOAR TESTIS

  • 1 January 1976
    • journal article
    • research article
    • Vol. 450  (3) , 441-449
Abstract
After incubation of [17,21,21,21-2H4]pregnenolone, which had been synthesized from nonlabeled pregnenolone by base-catalyzed exchange procedure, with the microsomal fraction of boar testis, [17-2H]androsta-5,16-dien-3.beta.-ol was identified as a metabolite. The identification has been performed by gas chromatography-mass spectrometry of the metabolite and of its hydrogenation product. Conclusive evidence on the location of the 2H atom at C-17 was obtained by transforming the metabolite to androsta-4,16-dien-3-one and then to androst-4-ene-3,17-dione and by proving that the former compound contained a 2H atom while the latter did not. In boar testis, androsta-5,16-dien-3.beta.-ol is probably synthesized from pregnenolone by a pathway in which 17.alpha.-H atom of pregnenolone is retained throughout the reaction, excluding 17.alpha.-hydroxypregnenolone and 3.beta.-hydroxyandrost-5-en17-one as intermediates.

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