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The Synthesis of Tritium-labeled 14agr-Methyl-5agr-cholest-7-en-3ß-ol and Its Enzymatic Demethylation

John C. Knight 1, Peter D. Klein 1, and Patricia A. Szczepanik 1

From the 1 From the Division of Biological and Medical Research, Argonne National Laboratory, Argonne, Illinois 60440

14agr-Methyl-5agr-cholest-7-en-3-one has been prepared and labeled with tritium by isotope exchange chromatography. Reduction with lithium aluminum hydride furnished pure, highly labeled 14agr-methyl-5agr-cholest-7-en-3ß-ol. Incubation of this compound with homogenates of rat liver results in its conversion to cholesterol, which has been identified by a variety of chemical and chromatographic techniques. The results show that enzymatic removal of the 14agr-methyl group from synthetic compounds is feasible, and offer a new approach to the study of the demethylation mechanism in steroid structures.

Submitted on May 19, 1965


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