Estrogen biosynthesis: concerning the obligatory intermediacy of 2β-hydroxy-10β-formylandrost-4-ene-3,17-dione

The transformation of an androgen to an estrogen by human placental aromatase was shown to involve three oxidative steps, each of which requires 1 mol of O sub(2) and 1 mol of NADPH. Fishman et al. proposed that the "third" mole of oxygen and of NADPH are utilized for the enzymatic 2 beta...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1984-01, Vol.106 (23), p.7282-7283
Main Authors: CASPI, E, WICHA, J, THANGAVEL ARUNACHALAM, NELSON, P, SPITELLER, G
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Other biological molecules
Terpenes, steroids. Hormones
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Summary:The transformation of an androgen to an estrogen by human placental aromatase was shown to involve three oxidative steps, each of which requires 1 mol of O sub(2) and 1 mol of NADPH. Fishman et al. proposed that the "third" mole of oxygen and of NADPH are utilized for the enzymatic 2 beta -hydroxylation of a 19-aldehyde intermediate to give, e.g., 2 beta -hydroxy-10 beta -formylandrost-4-ene-3,17-dione. To test the Fishman et al., hypothesis, the authors prepared (2 beta - super(18)O,19- super(3)H)-2 beta -hydroxy-10 beta -formylandrost-4-ene-3,17-dione 2-(tert-butyldimethylsilyl) ether.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00335a090