SYNTHESIS OF 16α-3H ANDROGEN AND ESTROGEN SUBSTRATES FOR 16α-HYDROXYLASE

Article abstract of DOI:10.1016/S0039-128X(81)80016-5

The synthesis of 16α-3H androgens and estrogens is described. 1-(3H)-Acetic acid in the presence of zinc dust reacts with 16α-bromo-17-ketosteroids to produce 16α-3H-17-ketosteroids.This chemical reaction was used to prepare 16α-3H-dehydroepiandrosterone (I) and 16α-3H-estrone acetate (XI) from 16α-bromo-dehydroepiandrosterone (X) and from 16α-bromo-estrone acetate (XII), respectively.Using appropriate microbiological techniques, it was possible to convert these radiolabelled substrates into 16α-3H-androstenedione (II) and 16α-3H-estradiol-17β (VII). 16α-3H-Estrone (VI) was obtained by the chemical hydrolysis of 16α-3H-estrone acetate.The label distribution as determined by microbiological 16α-hydroxylations indicated a specific labelling of 77percent for androgens and 65percent for estrogens in the 16α position.These substrates can be used for measuring the 16α hydroxylase activity, an important step in the biosynthesis of estriol (VIII) and estetrol (IX).