Studies on Ester Sulphates. 14. The in vitro Formation of Steroid Disulphates in Rat Liver Extracts.

Abstract

The in vitro synthesis of disulfates of certain dihydroxy steroids in an unfractionated cell-free rat liver enzyme system containing s35-labelled sulphate was demonstrated. Studies on the influence of various substitutions at the 17[alpha] position on sulfurylation of the 17[beta] hydroxyl group of various steroids have also been undertaken. In general, it is found that the ratio of disulfate to monosulfate formed is greatest at low substrate levels. The following observations are made with respect to the influence of steroid structure on the degree of sulfurylation: Of the 3, 17- and 3, 20-dihydroxy steroids studied, those having a 3[beta], 17[beta] and 3[beta], 20[beta] configuration of the hydroxyl groups are disulfurylated to the greatest extent. An ethyl or methyl group in the 17[alpha] position inhibits sulfurylation of the 17[beta] hydroxyl group. An ethinyl group in the corresponding position has no inhibitory effect on the sulfurylation of such a hydroxyl group. A double bond between the fourth and fifth carbon atoms inhibits sulfurylation of the 3[beta] hydroxyl group.