rational design and directed evolution of CYP102A1 (BM3) for regio-specific hydroxylation of isoflavone
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  • 作者:Sungghi Ko ; Yung-Hun Yang ; Kwon-Young Choi…
  • 关键词:cytochrome P450 monooxygenases ; self ; sufficient CYP102A1 ; isoflavone ; ortho ; specific hydroxylation ; regioselectivity
  • 刊名:Biotechnology and Bioprocess Engineering
  • 出版年:2015
  • 出版时间:April 2015
  • 年:2015
  • 卷:20
  • 期:2
  • 页码:225-233
  • 全文大小:717 KB
  • 参考文献:1.Wang, Q., X. Ge, X. Tian, Y. Zhang, J. Zhang, and P. Zhang (2013) Soy isoflavone: The multipurpose phytochemical (Review). Biomed. Rep. 1: 697鈥?01.
    2.Amit N. Shinde, N. M. and D. P. Fulzele (2009) Enhanced production of phytoestrogenic isoflavones from hairy root cultures of psoralea corylifolia l. Using elicitation and precursor feeding. Biotechnol. Bioproc. Eng. 14: 288鈥?94.View Article
    3.Liu, J., S. K. Chang, and D. Wiesenborn (2005) Antioxidant properties of soybean isoflavone extract and tofu in vitro and in vivo. J. Agricult. Food Chem. 53: 2333鈥?340.View Article
    4.Rimbach, G., S. De Pascual-Teresa, B. A. Ewins, S. Matsugo, Y. Uchida, A. M. Minihane, R. Turner, K. VafeiAdou, and P. D. Weinberg (2003) Antioxidant and free radical scavenging activity of isoflavone metabolites. Xenobiotica 33: 913鈥?25.View Article
    5.Park, J. S., J. S. Jung, Y. H. Jeong, J. W. Hyun, T. K. Le, D. H. Kim, E. C. Choi, and H. S. Kim (2011) Antioxidant mechanism of isoflavone metabolites in hydrogen peroxide-stimulated rat primary astrocytes: Critical role of hemeoxygenase-1 and NQO1 expression. J. Neurochem. 119: 909鈥?19.View Article
    6.Lee, D. E., K. W. Lee, S. Byun, S. K. Jung, N. Song, S. H. Lim, Y. S. Heo, J. E. Kim, N. J. Kang, B. Y. Kim, G. T. Bowden, A. M. Bode, H. J. Lee, and Z. Dong (2011) 7,3',4'-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J. Biol. Chem. 286: 14246鈥?4256.View Article
    7.Park, J. S., M. S. Woo, D. H. Kim, J. W. Hyun, W. K. Kim, J. C. Lee, and H. S. Kim (2007) Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells. J. Pharmacol. Exp. Therapeutics 320: 1237鈥?245.View Article
    8.Bernhardt, R. (2006) Cytochromes P450 as versatile biocatalysts. J. Biotechnol. 124: 128鈥?45.View Article
    9.Bernhardt, R. and V. B. Urlacher (2014) Cytochromes P450 as promising catalysts for biotechnological application: chances and limitations. Appl. Microbiol. Biotechnol. 98: 6185鈥?203.View Article
    10.Ringle, M., Y. Khatri, J. Zapp, F. Hannemann, and R. Bernhardt (2013) Application of a new versatile electron transfer system for cytochrome P450-based Escherichia coli whole-cell bioconversions. Appl. Microbiol. Biotechnol. 97: 7741鈥?754.View Article
    11.Munro, A. W., H. M. Girvan, and K. J. McLean (2007) Cytochrome P450鈥攔edox partner fusion enzymes. Biochimica et Biophysica Acta 1770: 345鈥?59.View Article
    12.Munro, A. W. and D. Leys (2012) Special issue: Cytochrome P450 structure and function: introduction. FEBS J. 279: 1515.View Article
    13.McLean, K. J., M. Sabri, K. R. Marshall, R. J. Lawson, D. G. Lewis, D. Clift, P. R. Balding, A. J. Dunford, A. J. Warman, J. P. McVey, A. M. Quinn, M. J. Sutcliffe, N. S. Scrutton, and A. W. Munro (2005) Biodiversity of cytochrome P450 redox systems. Biochem. Soc. Trans. 33: 796鈥?01.View Article
    14.De Mot, R. and A. H. Parret (2002) A novel class of self-sufficient cytochrome P450 monooxygenases in prokaryotes. Trends Microbiol. 10: 502鈥?08.View Article
    15.Choi, K. Y., E. Jung, D. H. Jung, B. P. Pandey, H. Yun, H. Y. Park, R. J. Kazlauskas, and B. G. Kim (2012) Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. The FEBS J. 279: 1650鈥?662.View Article
    16.Na-Rae Lee, J. W. Y. and Jin-Byung Park (2011) Effect of lipopolysaccharide mutation on oxygenation of linoleic acid by recombinant Escherichia coli expressing CYP102A2 of Bacillus subtilis. Biotechnol. Bioproc. Eng. 16: 7鈥?2.View Article
    17.Whitehouse, C. J., S. G. Bell, and L. L. Wong (2012) P450(BM3) (CYP102A1): Connecting the dots. Chem. Society Rev. 41: 1218鈥?260.View Article
    18.Budde, M., M. Morr, R. D. Schmid, and V. B. Urlacher (2006) Selective hydroxylation of highly branched fatty acids and their derivatives by CYP102A1 from Bacillus megaterium. ChemBio-Chem 7: 789鈥?94.View Article
    19.Whitehouse, C. J., W. Yang, J. A. Yorke, H. G. Tufton, L. C. Ogilvie, S. G. Bell, W. Zhou, M. Bartlam, Z. Rao, and L. L. Wong (2011) Structure, electronic properties and catalytic behaviour of an activity-enhancing CYP102A1 (P450(BM3)) variant. Dalton Trans. 40: 10383鈥?0396.View Article
    20.Whitehouse, C. J., S. G. Bell, W. Yang, J. A. Yorke, C. F. Blanford, A. J. Strong, E. J. Morse, M. Bartlam, Z. Rao, and L. L. Wong (2009) A highly active single-mutation variant of P450BM3 (CYP102A1). ChemBioChem 10: 1654鈥?656.View Article
    21.Seifert, A., M. Antonovici, B. Hauer, and J. Pleiss (2011) An efficient route to selective bio-oxidation catalysts: An iterative approach comprising modeling, diversification, and screening, based on CYP102A1. ChemBioChem 12: 1346鈥?351.View Article
    22.Damsten, M. C., B. M. van Vugt-Lussenburg, T. Zeldenthuis, J. S. de Vlieger, J. N. Commandeur, and N. P. Vermeulen (2008) Application of drug metabolising mutants of cytochrome P450 BM3 (CYP102A1) as biocatalysts for the generation of reactive metabolites. Chemico-Biol. Interact. 171: 96鈥?07.View Article
    23.Rea, V., S. Dragovic, J. S. Boerma, F. J. de Kanter, N. P. Vermeulen, and J. N. Commandeur (2011) Role of residue 87 in the activity and regioselectivity of clozapine metabolism by drugmetabolizing CYP102A1 M11H: Application for structural characterization of clozapine GSH conjugates. Drug Metabol. Disposition 39: 2411鈥?420.View Article
    24.Vottero, E., V. Rea, J. Lastdrager, M. Honing, N. P. Vermeulen, and J. N. Commandeur (2011) Role of residue 87 in substrate selectivity and regioselectivity of drug-metabolizing cytochrome P450 CYP102A1 M11. J. Biol. Inorganic Chem. 16: 899鈥?12.View Article
    25.Chen, C. K., T. Shokhireva, R. E. Berry, H. Zhang, and F. A. Walker (2008) The effect of mutation of F87 on the properties of CYP102A1-CYP4C7 chimeras: Altered regiospecificity and substrate selectivity. J. Biol. Inorganic Chem. 13: 813鈥?24.View Article
    26.Seifert, A., S. Vomund, K. Grohmann, S. Kriening, V. B. Urlacher, S. Laschat, and J. Pleiss (2009) Rational design of a minimal and highly enriched CYP102A1 mutant library with improved regio-, stereo- and chemoselectivity. ChemBioChem 10: 853鈥?61.View Article
    27.Whitehouse, C. J., W. Yang, J. A. Yorke, B. C. Rowlatt, A. J. Strong, C. F. Blanford, S. G. Bell, M. Bartlam, L. L. Wong, and Z. Rao (2010) Structural basis for the properties of two single-site proline mutants of CYP102A1 (P450BM3). ChemBioChem 11: 2549鈥?556.View Article
    28.Dietrich, M., S. Eiben, C. Asta, T. A. Do, J. Pleiss, and V. B. Urlacher (2008) Cloning, expression and characterisation of CYP102A7, a self-sufficient P450 monooxygenase from Bacillus licheniformis. Appl. Microbiol. Biotechnol. 79: 931鈥?40.View Article
    29.Choi, K. Y., E. Jung, H. Yun, Y. H. Yang, and B. G. Kim (2014) Engineering class I cytochrome P450 by gene fusion with NADPH-dependent reductase and S. avermitilis host development for daidzein biotransformation. Appl. Microbiol. Biotechnol. 98: 8191鈥?200.View Article
  • 作者单位:Sungghi Ko (1)
    Yung-Hun Yang (2)
    Kwon-Young Choi (3) (4)
    Byung-Gee Kim (1)

    1. School of Chemical and Biological Engineering, Seoul National University, Seoul, 151-742, Korea
    2. Department of Microbial Engineering, College of Engineering, Konkuk University, Seoul, 143-701, Korea
    3. Department of Environmental Engineering, College of Engineering, Ajou University, Suwon, 443-749, Korea
    4. Graduate school of Environment and Safety Engineering, Ajou University, Suwon, 443-749, Korea
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Biotechnology
  • 出版者:The Korean Society for Biotechnology and Bioengineering
  • ISSN:1976-3816
文摘
Isoflavonoids are a class of polycyclic aromatic hydrocarbon compounds originating from plants as secondary metabolites. Their oxidative metabolites such as ortho dihydroxyisoflavones (ODIs), where the ortho carbons of the hydroxyl groups are hydroxylated, have been reported to have a remarkably high antioxidant effect. Here, we report enzyme engineering of the cytochrome P450 enzyme CYP102A1 (BM3) for the synthesis of ODIs from isoflavonoids.

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