Steroids p. 399 - 410 (1982)
Update date:2022-07-30
Topics:
Hobe, G.
Schoen, R.
Hoerhold, C.
Huebner, M.
Schade, W.
Schubert, K.
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.
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Doi:10.1016/S0008-6215(00)81803-0
(1982)Doi:10.1039/c39760000105
(1976)Doi:10.1016/S0040-4039(98)01788-2
(1998)Doi:10.1039/b305458f
(2003)Doi:10.1007/BF00513427
(1982)Doi:10.1021/ja0433370
(2005)
