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Volumn 14, Issue 1, 2015, Pages

Process development for the production of 15β-hydroxycyproterone acetate using Bacillus megaterium expressing CYP106A2 as whole-cell biocatalyst

Author keywords

Bacillus megaterium; Bioreactor; Cyclodextrin; CYP106A2; Cyproterone acetate; Cytochrome P450; Steroid hydroxylase; Whole cell biocatalyst

Indexed keywords

15BETA HYDROXYCYPROTERONE ACETATE; 2 HYDROXYPROPYL BETA CYCLODEXTRIN; CYPROTERONE ACETATE; CYPROTERONE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 106A2; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG; 15BETA-HYDROXYLASE CYP106A2, BACILLUS MEGATERIUM; 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN; BACTERIAL PROTEIN; BETA CYCLODEXTRIN DERIVATIVE; RECOMBINANT PROTEIN;

EID: 84928730984     PISSN: None     EISSN: 14752859     Source Type: Journal    
DOI: 10.1186/s12934-015-0210-z     Document Type: Article
Times cited : (27)

References (38)
  • 1
    • 84903598617 scopus 로고    scopus 로고
    • Cytochromes P450 as promising catalysts for biotechnological application: chances and limitations
    • Bernhardt R, Urlacher VB. Cytochromes P450 as promising catalysts for biotechnological application: chances and limitations. Appl Microbiol Biotechnol. 2014;98(14):6185-203.
    • (2014) Appl Microbiol Biotechnol , vol.98 , Issue.14 , pp. 6185-6203
    • Bernhardt, R.1    Urlacher, V.B.2
  • 2
    • 84866309060 scopus 로고    scopus 로고
    • Microbial steroid transformations: current state and prospects
    • Donova MV, Egorova OV. Microbial steroid transformations: current state and prospects. Appl Microbiol Biotechnol. 2012;94(6):1423-47.
    • (2012) Appl Microbiol Biotechnol , vol.94 , Issue.6 , pp. 1423-1447
    • Donova, M.V.1    Egorova, O.V.2
  • 3
    • 84889469275 scopus 로고    scopus 로고
    • Steroid hydroxylation: microbial steroid biotransformations using cytochrome P450 enzymes
    • Schmid RD, Urlacher VB, editors KGaA, Weinheim: Wiley-VCH Verlag GmbH & Co
    • Bureik M, Bernhardt R. Steroid hydroxylation: microbial steroid biotransformations using cytochrome P450 enzymes. In: Schmid RD, Urlacher VB, editors. Modern Biooxidation: Enzymes, Reactions and Applications. KGaA, Weinheim: Wiley-VCH Verlag GmbH & Co; 2007. p. 155-76.
    • (2007) Modern Biooxidation: Enzymes, Reactions and Applications , pp. 155-176
    • Bureik, M.1    Bernhardt, R.2
  • 4
    • 68549112862 scopus 로고    scopus 로고
    • Microbial biotransformation: recent developments on steroid drugs
    • Tong W, Dong X. Microbial biotransformation: recent developments on steroid drugs. Recent Pat Biotechnol. 2009;3(2):141-53.
    • (2009) Recent Pat Biotechnol , vol.3 , Issue.2 , pp. 141-153
    • Tong, W.1    Dong, X.2
  • 5
    • 77949832008 scopus 로고    scopus 로고
    • Towards preparative scale steroid hydroxylation with cytochrome P450 monooxygenase CYP106A2
    • Zehentgruber D, Hannemann F, Bleif S, Bernhardt R, Lütz S. Towards preparative scale steroid hydroxylation with cytochrome P450 monooxygenase CYP106A2. ChemBioChem. 2010;11(5):713-21.
    • (2010) ChemBioChem , vol.11 , Issue.5 , pp. 713-721
    • Zehentgruber, D.1    Hannemann, F.2    Bleif, S.3    Bernhardt, R.4    Lütz, S.5
  • 6
    • 2642562736 scopus 로고    scopus 로고
    • Identification of monohydroxy progesterones produced by CYP106A2 using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry
    • Lisurek M, Kang M, Hartmann RW, Bernhardt R. Identification of monohydroxy progesterones produced by CYP106A2 using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry. Biochem Biophys Res Commun. 2004;319(2):677-82.
    • (2004) Biochem Biophys Res Commun , vol.319 , Issue.2 , pp. 677-682
    • Lisurek, M.1    Kang, M.2    Hartmann, R.W.3    Bernhardt, R.4
  • 7
    • 0017129148 scopus 로고
    • Characterization of a cytochrome P-450-dependent steroid hydroxylase system present in Bacillus megaterium
    • Berg A, Gustafsson JA, Ingelman-Sundberg M. Characterization of a cytochrome P-450-dependent steroid hydroxylase system present in Bacillus megaterium. J Biol Chem. 1976;251(9):2831-8.
    • (1976) J Biol Chem , vol.251 , Issue.9 , pp. 2831-2838
    • Berg, A.1    Gustafsson, J.A.2    Ingelman-Sundberg, M.3
  • 8
    • 84941993531 scopus 로고    scopus 로고
    • Comparison of CYP106A1 and CYP106A2 from Bacillus megaterium-identification of a novel 11-oxidase activity
    • In press
    • Kiss FM, Schmitz D, Zapp J, Bernhardt R. Comparison of CYP106A1 and CYP106A2 from Bacillus megaterium-identification of a novel 11-oxidase activity. Appl Microbiol Biotechnol. 2015; In press.
    • (2015) Appl Microbiol Biotechnol
    • Kiss, F.M.1    Schmitz, D.2    Zapp, J.3    Bernhardt, R.4
  • 9
    • 84856382805 scopus 로고    scopus 로고
    • A new Bacillus megaterium whole-cell catalyst for the hydroxylation of the pentacyclic triterpene 11-keto-β-boswellic acid (KBA) based on a recombinant cytochrome P450 system
    • Bleif S, Hannemann F, Zapp J, Hartmann D, Jauch J, Bernhardt R. A new Bacillus megaterium whole-cell catalyst for the hydroxylation of the pentacyclic triterpene 11-keto-β-boswellic acid (KBA) based on a recombinant cytochrome P450 system. Appl Microbiol Biotechnol. 2012;93(3):1135-46.
    • (2012) Appl Microbiol Biotechnol , vol.93 , Issue.3 , pp. 1135-1146
    • Bleif, S.1    Hannemann, F.2    Zapp, J.3    Hartmann, D.4    Jauch, J.5    Bernhardt, R.6
  • 10
    • 79952021883 scopus 로고    scopus 로고
    • Identification of CYP106A2 as a Regioselective Allylic Bacterial Diterpene Hydroxylase
    • Bleif S, Hannemann F, Lisurek M, von Kries JP, Zapp J, Dietzen M, et al. Identification of CYP106A2 as a Regioselective Allylic Bacterial Diterpene Hydroxylase. ChemBioChem. 2011;12(4):576-82.
    • (2011) ChemBioChem , vol.12 , Issue.4 , pp. 576-582
    • Bleif, S.1    Hannemann, F.2    Lisurek, M.3    von Kries, J.P.4    Zapp, J.5    Dietzen, M.6
  • 11
    • 84860213923 scopus 로고    scopus 로고
    • Hydroxylation of the triterpenoid dipterocarpol with CYP106A2 from Bacillus megaterium
    • Schmitz D, Zapp J, Bernhardt R. Hydroxylation of the triterpenoid dipterocarpol with CYP106A2 from Bacillus megaterium. FEBS J. 2012;279(9):1663-74.
    • (2012) FEBS J , vol.279 , Issue.9 , pp. 1663-1674
    • Schmitz, D.1    Zapp, J.2    Bernhardt, R.3
  • 12
    • 84903765191 scopus 로고    scopus 로고
    • Steroid conversion with CYP106A2-production of pharmaceutically interesting DHEA metabolites
    • Schmitz D, Zapp J, Bernhardt R. Steroid conversion with CYP106A2-production of pharmaceutically interesting DHEA metabolites. Microb Cell Fact. 2014;13:81.
    • (2014) Microb Cell Fact , vol.13 , pp. 81
    • Schmitz, D.1    Zapp, J.2    Bernhardt, R.3
  • 13
    • 33744821345 scopus 로고    scopus 로고
    • Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases
    • Hannemann F, Virus C, Bernhardt R. Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases. J Biotechnol. 2006;124(1):172-81.
    • (2006) J Biotechnol , vol.124 , Issue.1 , pp. 172-181
    • Hannemann, F.1    Virus, C.2    Bernhardt, R.3
  • 15
    • 0024507419 scopus 로고
    • Highly efficient expression of homologous and heterologous genes in Bacillus megaterium
    • Meinhardt F, Stahl U, Ebeling W. Highly efficient expression of homologous and heterologous genes in Bacillus megaterium. Appl Microbiol Biotechnol. 1989;30(4):343-50.
    • (1989) Appl Microbiol Biotechnol , vol.30 , Issue.4 , pp. 343-350
    • Meinhardt, F.1    Stahl, U.2    Ebeling, W.3
  • 16
    • 12544253339 scopus 로고    scopus 로고
    • Protein and vitamin production in Bacillus megaterium
    • Barg H, Malten M, Jahn M, Jahn D. Protein and vitamin production in Bacillus megaterium. Methods Biotechnol. 2005;18:205-23.
    • (2005) Methods Biotechnol , vol.18 , pp. 205-223
    • Barg, H.1    Malten, M.2    Jahn, M.3    Jahn, D.4
  • 18
    • 0022818061 scopus 로고
    • Pharmacology of antiandrogens
    • Neumann F, Toepert M. Pharmacology of antiandrogens. J Steroid Biochem. 1986;25(5):885-95.
    • (1986) J Steroid Biochem , vol.25 , Issue.5 , pp. 885-895
    • Neumann, F.1    Toepert, M.2
  • 19
    • 0021989016 scopus 로고
    • 15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine
    • Frith RG, Phillipou G. 15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine. J Chromatogr Biomed Appl. 1985;338(1):179-86.
    • (1985) J Chromatogr Biomed Appl , vol.338 , Issue.1 , pp. 179-186
    • Frith, R.G.1    Phillipou, G.2
  • 21
    • 84925535983 scopus 로고    scopus 로고
    • Guidelines for development and implementation of biocatalytic P450 processes
    • In press
    • Lundemo MT, Woodley JM. Guidelines for development and implementation of biocatalytic P450 processes. Appl Microbiol Biotechnol. 2015; In press.
    • (2015) Appl Microbiol Biotechnol
    • Lundemo, M.T.1    Woodley, J.M.2
  • 22
    • 84861303750 scopus 로고    scopus 로고
    • Adrenodoxin-a versatile ferredoxin
    • Ewen KM, Ringle M, Bernhardt R. Adrenodoxin-a versatile ferredoxin. IUBMB Life. 2012;64(6):506-12.
    • (2012) IUBMB Life , vol.64 , Issue.6 , pp. 506-512
    • Ewen, K.M.1    Ringle, M.2    Bernhardt, R.3
  • 23
    • 33947690713 scopus 로고    scopus 로고
    • Batch and continuous transformation of progesterone by Rhizopus nigricans pellets in the presence of β-cyclodextrin
    • Roglic U, Plazl I, Znidarsic-Plazl P. Batch and continuous transformation of progesterone by Rhizopus nigricans pellets in the presence of β-cyclodextrin. Biocatal Biotransform. 2007;25(1):16-23.
    • (2007) Biocatal Biotransform , vol.25 , Issue.1 , pp. 16-23
    • Roglic, U.1    Plazl, I.2    Znidarsic-Plazl, P.3
  • 24
    • 0025773494 scopus 로고
    • Microbial transformations in a cyclodextrin mediu. Part 2. Reduction of androstenedione to testosterone by Saccharomyces cerevisiae
    • Singer Y, Shity H, Bar R. Microbial transformations in a cyclodextrin medium. Part 2. Reduction of androstenedione to testosterone by Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 1991;35(6):731-7.
    • (1991) Appl Microbiol Biotechnol , vol.35 , Issue.6 , pp. 731-737
    • Singer, Y.1    Shity, H.2    Bar, R.3
  • 25
    • 0035649181 scopus 로고    scopus 로고
    • Chemical and biochemical hydroxylations of steroids. A review
    • Pellissier H, Santelli M. Chemical and biochemical hydroxylations of steroids. A review. Org Prep Proced Int. 2001;33(1):1-58.
    • (2001) Org Prep Proced Int , vol.33 , Issue.1 , pp. 1-58
    • Pellissier, H.1    Santelli, M.2
  • 26
    • 84885838418 scopus 로고    scopus 로고
    • ChemSpider. [http://www.chemspider.com/Chemical-Structure.9496.html]
    • ChemSpider
  • 27
    • 84885838418 scopus 로고    scopus 로고
    • ChemSpider. [http://www.chemspider.com/Chemical-Structure.143151.html]
    • ChemSpider
  • 28
    • 0023385987 scopus 로고
    • Rules for optimization of biocatalysis in organic solvents
    • Laane C, Boeren S, Vos K, Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng. 1987;30(1):81-7.
    • (1987) Biotechnol Bioeng , vol.30 , Issue.1 , pp. 81-87
    • Laane, C.1    Boeren, S.2    Vos, K.3    Veeger, C.4
  • 29
    • 10444279209 scopus 로고    scopus 로고
    • Cyclodextrin-based pharmaceutics: past, present and future
    • Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discovery. 2004;3(12):1023-35.
    • (2004) Nat Rev Drug Discovery , vol.3 , Issue.12 , pp. 1023-1035
    • Davis, M.E.1    Brewster, M.E.2
  • 30
    • 84925521874 scopus 로고    scopus 로고
    • Hydroxypropyl-β-cyclodextrin-mediated alterations in cell permeability, lipid and protein profiles of steroid-transforming Arthrobacter simplex
    • Shen Y, Liang J, Li H, Wang M. Hydroxypropyl-β-cyclodextrin-mediated alterations in cell permeability, lipid and protein profiles of steroid-transforming Arthrobacter simplex. Appl Microbiol Biotechnol. 2014 doi:10.1007/s00253-014-6089-5.
    • (2014) Appl Microbiol Biotechnol
    • Shen, Y.1    Liang, J.2    Li, H.3    Wang, M.4
  • 31
    • 0036890313 scopus 로고    scopus 로고
    • Biotechnological applications of cyclodextrins
    • Singh M, Sharma R, Banerjee UC. Biotechnological applications of cyclodextrins. Biotechnol Adv. 2002;20(5-6):341-59.
    • (2002) Biotechnol Adv , vol.20 , Issue.5-6 , pp. 341-359
    • Singh, M.1    Sharma, R.2    Banerjee, U.C.3
  • 32
    • 0028919496 scopus 로고
    • Inactivation of the major extracellular protease from Bacillus megaterium DSM319 by gene replacement
    • Wittchen K, Meinhardt F. Inactivation of the major extracellular protease from Bacillus megaterium DSM319 by gene replacement. Appl Microbiol Biotechnol. 1995;42(6):871-7.
    • (1995) Appl Microbiol Biotechnol , vol.42 , Issue.6 , pp. 871-877
    • Wittchen, K.1    Meinhardt, F.2
  • 33
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem. 1964;239(7):2370-8.
    • (1964) J Biol Chem , vol.239 , Issue.7 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 34
    • 0034708263 scopus 로고    scopus 로고
    • Substrate Binding to 15β-Hydroxylase (CYP106A2) Probed by FT Infrared Spectroscopic Studies of the Iron Ligand CO Stretch Vibration
    • Simgen B, Contzen J, Schwarzer R, Bernhardt R, Jung C. Substrate Binding to 15β-Hydroxylase (CYP106A2) Probed by FT Infrared Spectroscopic Studies of the Iron Ligand CO Stretch Vibration. Biochem Biophys Res Commun. 2000;269(3):737-42.
    • (2000) Biochem Biophys Res Commun , vol.269 , Issue.3 , pp. 737-742
    • Simgen, B.1    Contzen, J.2    Schwarzer, R.3    Bernhardt, R.4    Jung, C.5
  • 35
    • 0027292014 scopus 로고
    • Direct expression of adrenodoxin reductase in Escherichia coli and the functional characterization
    • Sagara Y, Wada A, Takata Y, Waterman MR, Sekimizu K, Horiuchi T. Direct expression of adrenodoxin reductase in Escherichia coli and the functional characterization. Biol Pharm Bull. 1993;16(7):627-30.
    • (1993) Biol Pharm Bull , vol.16 , Issue.7 , pp. 627-630
    • Sagara, Y.1    Wada, A.2    Takata, Y.3    Waterman, M.R.4    Sekimizu, K.5    Horiuchi, T.6
  • 36
    • 0026496878 scopus 로고
    • Expression of bovine adrenodoxin in E. coli and site-directed mutagenesis of /2 Fe-2S/cluster ligands
    • Uhlmann H, Beckert V, Schwarz D, Bernhardt R. Expression of bovine adrenodoxin in E. coli and site-directed mutagenesis of /2 Fe-2S/cluster ligands. Biochem Biophys Res Commun. 1992;188(3):1131-8.
    • (1992) Biochem Biophys Res Commun , vol.188 , Issue.3 , pp. 1131-1138
    • Uhlmann, H.1    Beckert, V.2    Schwarz, D.3    Bernhardt, R.4
  • 37
    • 84859891750 scopus 로고    scopus 로고
    • Debottlenecking recombinant protein production in Bacillus megaterium under large-scale conditions-targeted precursor feeding designed from metabolomics
    • Korneli C, Bolten CJ, Godard T, Franco-Lara E, Wittmann C. Debottlenecking recombinant protein production in Bacillus megaterium under large-scale conditions-targeted precursor feeding designed from metabolomics. Biotechnol Bioeng. 2012;109(6):1538-50.
    • (2012) Biotechnol Bioeng , vol.109 , Issue.6 , pp. 1538-1550
    • Korneli, C.1    Bolten, C.J.2    Godard, T.3    Franco-Lara, E.4    Wittmann, C.5
  • 38
    • 0017661459 scopus 로고
    • Isolation and identification of 15-β-hydroxycyproterone acetate as a new metabolite of cyproterone acetate in dog, monkey and man
    • Bhargava AS, Seeger A, Guenzel P. Isolation and identification of 15-β-hydroxycyproterone acetate as a new metabolite of cyproterone acetate in dog, monkey and man. Steroids. 1977;30(3):407-18.
    • (1977) Steroids , vol.30 , Issue.3 , pp. 407-418
    • Bhargava, A.S.1    Seeger, A.2    Guenzel, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.