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A simple two-step method for the conversion of [3H]cortisol to [3H]-11-ketotestosterone.

Steroids (1997-11-05)
P M Lokman, J L Irwin, L F Blackwell, P S Davie, M Thomas, G Young
ABSTRACT

Despite the existence of several protocols, problems appear to persist in the small scale chemical synthesis of radiolabeled 11-ketotestosterone from cortisol. We investigated the possibilities of using the mild oxidant pyridinium dichromate for the oxidative cleavage of the dihydroxyacetone side chain of cortisol and 17 beta-hydroxysteroid dehydrogenase for the subsequent reduction of the resulting 17-keto group. Our protocol has resulted in consistently high yields of both the intermediate, adrenosterone (70-80%), and the product, 11-ketotestosterone (up to 60%). This, taken together with the convenience and relatively low cost of our method, recommends the protocol for its use for the synthesis of [3H]-11-ketotestosterone for endocrine studies.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyridinium dichromate, 98%
Sigma-Aldrich
Adrenosterone, 98%