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Microbial transformation of 17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17
Abstract:
Microbial transformation of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds: 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3, 17-diol, 17 alpha-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers. The analogous compound without the 9(10) double bond, 17 alpha-cyanomethyl-19-nortestosterone, was transformed mainly to 5 alpha-hydrogenated metabolites: 17 alpha-cyanomethyl-17-hydroxy-5 alpha-estran-3-one, 17 alpha-cyanomethyl-17-hydroxy-5 alpha-1-estren-3-one, 17 alpha-cyanomethyl-5 alpha-estrane-3 alpha, 17-diol, and 17 alpha-cyanomethyl-5 alpha-estrane-3 beta, 17-diol. From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5 alpha-hydrogenation.