A simple two-step method for the conversion of [3H]cortisol to [3H]-11-ketotestosterone.
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.
Lokman
P M
PM
Department of Zoology, University of Otago, Dunedin, New Zealand. mlokman@pop.fish.hokudai.ac.jp
Irwin
J L
JL
Blackwell
L F
LF
Davie
P S
PS
Thomas
M
M
Young
G
G
D000736:Androstenes / Q000737:chemistry / Q000378:metabolism; D006854:Hydrocortisone / Q000737:chemistry*; D006913:Hydroxysteroid Dehydrogenases / Q000378:metabolism; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds; D013739:Testosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D014316:Tritium
D000736:Androstenes; D011726:Pyridinium Compounds; D014316:Tritium; C061685:pyridinium dichromate; D013739:Testosterone; C011657:adrenosterone; D006913:Hydroxysteroid Dehydrogenases; C035507:3(17)-hydroxysteroid dehydrogenase; C003600:11-ketotestosterone; D006854:Hydrocortisone