A Biochemical Effect of Deuterium

Journal/Book: (Reprinted from Nature Vol. 191 No. 4795 pp. 1294--1295 September 23. 1961). 1961;

Abstract: AMONG the naturally occurring steroid hormones and metabolites the androgens are uniquo in that 3-hydroxy-5-androstanes exhibit high hormonal activity the 3-hydroxy (axial) compounds being highly active while the 3ß-hydroxy (equatorial) compounds are much weaker androgens. It is known from both chemical and microbiological work1 that the 3-alcohols are oxidized more readily to the corresponding 3-ketone than are the 3ß-alcohols in accordance with the thermodynamic prediction. It is further known that enzymic oxidation of 3-hydroxy-5-androstanes occurs in mammalian tissue in particular in the liver. This suggests the possibility that in vivo these compounds are oxidized in various degrees to the even more potent androgens the 3-keto-5-androstanes and that in fact the 3-alcohols may be androgenically inactive per se. . . .

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