title: Microbial transformation of 17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17 alpha-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis.
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.
mesh_terms: D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D006865:Hydrogenation; D009161:Mycobacterium / Q000378:metabolism*; D009277:Nandrolone / Q000031:analogs & derivatives* / Q000378:metabolism
chemical_list: C023635:dienogest; C036443:17 alpha-cyanomethyl-19-nortestosterone; D009277:Nandrolone