title: Bioconversion of 6-(N-methyl-N-phenyl)aminomethyl androstane steroids by Nocardioides simplex.
abstract: The newly synthesized (α/β)-diastereomers of 6-(N-methyl-N-phenyl)aminomethylandrost-4-ene-3,17-dione (5) and 6-(N-methyl-N-phenyl)aminomethylandrost-4-en-17β-ol-3-one (6) were firstly investigated as substrates for the whole cells of Nocardioides simplex VKM Ac-2033D in comparison with their unsubstituted analogs, - androst-4-ene-3,17-dione (1) and androst-4-en-17β-ol-3-one (2). 1(2)-Dehydroderivatives were identified as the major bioconversion products from all the substrates tested. When using the mixtures of (α/β)-stereoisomers of 5 and 6 as the substrates, only β-stereoisomers of the corresponding 1,4-diene-steroids were formed. Along with 1(2)-dehydrogenation, N. simplex VKM Ac-2033D promoted oxidation of the hydroxyl group at C-17 position of 6: both 6(α) and 6(β) were transformed to the corresponding 17-keto derivatives. No steroid core destruction was observed during the conversion of the 6-substituted androstanes 5 and 6, while it was significant when 1 or 2 was used as the substrate. The results suggested high potentials of N. simplex VKM Ac-2033D for the generation of novel 1(2)-dehydroanalogs.
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospekt Nauki, 5, Puschino, Moscow Region 142290, Russian Federation. Electronic address: sukhodolskaya@rambler.ru.
authors.forename: Galina
authors.initials: G
authors.lastname: Sukhodolskaya
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospekt Nauki, 5, Puschino, Moscow Region 142290, Russian Federation. Electronic address: vvfokina@rambler.ru.
authors.forename: Victoria
authors.initials: V
authors.lastname: Fokina
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospekt Nauki, 5, Puschino, Moscow Region 142290, Russian Federation. Electronic address: w___w@rambler.ru.
authors.forename: Andrei
authors.initials: A
authors.lastname: Shutov
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospekt Nauki, 5, Puschino, Moscow Region 142290, Russian Federation. Electronic address: nikolae_vera@rambler.ru.
authors.forename: Vera
authors.initials: V
authors.lastname: Nikolayeva
authors.affiliation: Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskiye gory, 1-3, Moscow 119991, Russian Federation. Electronic address: tatiana_savinova@rambler.ru.
authors.forename: Tatiana
authors.initials: T
authors.lastname: Savinova
authors.affiliation: Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskiye gory, 1-3, Moscow 119991, Russian Federation. Electronic address: grishin@nmr.chem.msu.ru.
authors.forename: Yuri
authors.initials: Y
authors.lastname: Grishin
authors.affiliation: Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskiye gory, 1-3, Moscow 119991, Russian Federation. Electronic address: mak@org.chem.msu.ru.
authors.forename: Alexey
authors.initials: A
authors.lastname: Kazantsev
authors.affiliation: Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskiye gory, 1-3, Moscow 119991, Russian Federation. Electronic address: nvlukashev@gmail.com.
authors.forename: Nikolay
authors.initials: N
authors.lastname: Lukashev
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospekt Nauki, 5, Puschino, Moscow Region 142290, Russian Federation. Electronic address: donova-marina@rambler.ru.
authors.forename: Marina
authors.initials: M
authors.lastname: Donova
mesh_terms: D039903:Actinobacteria / Q000378:metabolism; D000731:Androstanes / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000731:Androstanes; D013256:Steroids; C033936:androstane
keywords: 3-Ketosteroid Δ(1)-dehydrogenase; 6(α/β)-(N-methyl-N-phenyl)aminomethyl androstanes; Actinobacteria; Androst-4-ene-3,17-dione (PubChem CID: 6128); Androsta-1,4-diene-3,17-dione (PubChem CID: 13472); Biotransformation; Dehydrotestosterone (PubChem CID: 6422); Nocardioides simplex; Testosterone (PubChem CID: 6013)