| Title: | The mechanism of the synthesis of 16-androstenes in human testicular homogenates |
| Author(s): | Weusten JJ; Legemaat G; van der Wouw MP; Smals AG; Kloppenborg PW; Benraad T; |
| Address: | "Department of Medicine, St. Radboud Hospital, University of Nijmegen, The Netherlands" |
| DOI: | 10.1016/0022-4731(89)90513-x |
| ISSN/ISBN: | 0022-4731 (Print) 0022-4731 (Linking) |
| Abstract: | "The biochemical pathway leading to the 16-unsaturated C19 steroids--known as sex pheromone (precursors) in pig and man--is still a matter of dispute. In the 16-ene-synthetase process, via which 5,16-androstadien-3 beta-ol (ADL) or 4,16-androstadien-3-one (ADN) are biosynthesized from pregnenolone (P5) or progesterone (P4), a number of 2 or even 3 step conversions have been suggested in porcine tests, including 20 beta-reduction, 21-hydroxylation and 16,17-dehydrogenation. Studying the 16-ene-synthetase reaction in human testicular homogenates, we adduced evidence for the hypothesis that ADL is synthesized from P5 in a single step, not requiring separate intermediates. Our proposal for the 16-ene-synthetase mechanism also explains why, at least in our hands, synthesis of ADL is always accompanied by co-synthesis of its satellite 5-androstene-3 beta,17 alpha-diol (epiA5): both steroids are synthesized as a mere consequence of the fact that the proposed elimination and substitution reactions for the synthesis of ADL and epiA5, respectively, are competitive processes" |
| Keywords: | "Androstenes/*biosynthesis Androstenols/biosynthesis Humans In Vitro Techniques Male Models, Chemical Oxidoreductases/*metabolism Pregnenolone/metabolism Testis/*metabolism;" |
| Notes: | "MedlineWeusten, J J Legemaat, G van der Wouw, M P Smals, A G Kloppenborg, P W Benraad, T eng England 1989/05/01 J Steroid Biochem. 1989 May; 32(5):689-94. doi: 10.1016/0022-4731(89)90513-x" |
