MICROBIAL TRANSFORMATION OF 17α-CYANOMETHYL-17-HYDROXY-4,9-ESTRADIEN-3-ONE (STS 557) AND 17α-CYANOMETHYL-19-NORTESTOSTERONE BY MYCOBACTERIUM SMEGMATIS

Article abstract of DOI:10.1016/0039-128X(82)90064-2

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