Cytochrome P450 bioreactors in the pharmaceutical industry: Challenges and opportunities

Current Topics in Medicinal Chemistry

Volumn 13, Issue 12, 2013, Pages 1470-1490

  Martinez, Carlos A ^a   Rupasinghe, Sanjeewa G ^a  

^a PFIZER INC   (United States)

Author keywords

Bioreactor; Challenges; CYP; Oxidation; Pharmaceutical; Preparation; Scale up

Indexed keywords

ASTEMIZOLE; BUSPIRONE; CHLORZOXAZONE; CHOLESTEROL 7ALPHA MONOOXYGENASE; CYCLOHEXANE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 BM3; DICLOFENAC; FERREDOXIN; FORMATE DEHYDROGENASE; GLUCOSE 6 PHOSPHATE DEHYDROGENASE; GLUCOSE DEHYDROGENASE; GLYCEROL DEHYDROGENASE; HYDROGEN PEROXIDE; ISOCITRATE DEHYDROGENASE; LIVER ENZYME; OUTER MEMBRANE PROTEIN; PROGESTERONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TESTOSTERONE; UNINDEXED DRUG; UNSPECIFIC MONOOXYGENASE; VERAPAMIL;

BIOCATALYSIS; BIOREACTOR; BIOTRANSFORMATION; DRUG INDUSTRY; DRUG METABOLISM; ELECTRON TRANSPORT; ENZYME ENGINEERING; ENZYME SPECIFICITY; ESCHERICHIA COLI; GENE EXPRESSION; HUMAN; MOLECULAR WEIGHT; NONHUMAN; PERFORMANCE; PRODUCTIVITY; PROMOTER REGION; PROTEIN ENGINEERING; REVIEW;

BIOREACTORS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INDUSTRY; OXIDATION-REDUCTION; PROTEIN ENGINEERING;

EID: 84881341237     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/15680266113139990111     Document Type: Review

References (304)

1. Peterson, D.; Murray, H.; Eppstein, S.; Reineke, L.; Weintraub, A.; Meister, P.; Leigh, H. Microbiological Transformations of Steroids. 1 I. Introduction of Oxygen at Carbon-11 of Progesterone. J. Am. Chem. Soc., 1952, 74(23), 5933-5936.
2. Peterson, D.H.; Murray, H.C. Microbiological oxygenation of steroids at carbon 11. J. Am. Chem. Soc., 1952, 74(7), 1871-1872.
3. Colingsworth, D.R.; Brunner, M.P.; Haines, W.J. A partial microbiological synthesis of adrenal cortex hormones. J. Am. Chem. Soc., 1952, 74(9), 2381-2382.
4. Mahato, S.B.; Garai, S. Advances in microbial steroid biotransformation. Steroids, 1997, 62(4), 332-345.
5. Donova, M.V.; Egorova, O.V. Microbial steroid transformations: current state and prospects. Appl. Microbiol. Biotechnol., 2012, 1-25.
6. Jones, E.R.H. The microbiological hydroxylation of steroids and related compounds. Pure Appl. Chem, 1973, 33(1), 39-52.
7. Hogg, J.A. Steroids, the steroid community, and Upjohn in perspective: a profile of innovation. Steroids, 1992, 57(12), 593-616.
8. Payne, A.H.; Hales, D.B. Overview of steroidogenic enzymes in the pathway from cholesterol to active steroid hormones. Endocr. Rev., 2004, 25(6), 947-970.
9. Makovec, T.; Breskvar, K. Purification of cytochrome P450 from filamentous fungus Rhyzopus nigricans. Pflügers Arch. Eur. J. Physiol.,2000, 439(7), 111-112.
10. Zehentgruber, D.; Hannemann, F.; Bleif, S.; Bernhardt, R.; Lütz, S. Towards Preparative Scale Steroid Hydroxylation with Cytochrome P450 Monooxygenase CYP106A2. ChemBioChem, 2010, 11(5), 713-721.
11. Lu, W.; Du, L.; Wang, M.; Jia, X.; Wen, J.; Huang, Y.; Guo, Y.; Gong, W.; Bao, H.; Yang, J.; Sun, B. Optimisation of Hydrocortisone Production by Curvularia lunata. Appl. Biochem. Biotechnol., 2007, 142(1), 17-28.
12. Ahmed, F.; Williams, R.A.D.; Smith, K.E. Microbial transformation of steroids-IX. Purification of progesterone hydroxylase cytochrome P-450 from Phycomyces blakesleeanus. J. Steroid Biochem. Mol. Biol.,1995, 52(2), 203-208.
13. Breskvar, K.; Ferenčak, Z.; Hudnik-Plevnik, T. The role of cytochrome P45011α in detoxification of steroids in the filamentous fungus Rhizopus nigricans. J. Steroid Biochem. Mol. Biol., 1995, 52(3), 271-275.
14. Dlugoński, J.; Bartnicka, K.; Zemelko, I.; Chojecka, V.; Sedlaczek, L. Determination of cytochrome P-450 in Cunninghamella elegans intact protoplasts and cell-free preparations capable of steroid hydroxylation. J. Basic Microbiol., 1991, 31(5), 347-356.
15. Irrgang, S.; Schlosser, D.; Fritsche, W. Involvement of cytochrome P-450 in the 15α-hydroxylation of 13-ethyl-gon-4-ene-3,17-dione by Penicillium raistrickii. J. Steroid Biochem. Mol. Biol., 1997, 60(5-6), 339-346.
16. Samanta, T.B.; Ghosh, D.K. Characterization of progesterone 11 [alpha]-hydroxylase of Aspergillus ochraceus TS: A cytochrome P-450 linked monooxygenase. J. Steroid Biochem., 1987, 28(3), 327-332.
17. Smith, K.E.; Ahmed, F.; Williams, R.A.D.; Kelly, S.L. Microbial transformations of steroids-VIII. Transformation of progesterone by whole cells and microsomes of Aspergillus fumigatus. J. Steroid Biochem. Mol. Biol., 1994, 49(1), 93-100.
18. Bureik, M.; Bernhardt, R. In Modern Biooxidation; Wiley-VCH Verlag GmbH & Co. KGaA, 2007, pp 155-176.
19. Omura, T. Forty years of cytochrome P450. Biochem. Biophys. Res. Commun., 1999, 266(3), 690-698.
20. De Montellano, P.R.O. Cytochrome P450: structure, mechanism, and biochemistry. Springer, 2005.
21. Bernhardt, R. Cytochromes P450 as versatile biocatalysts. J. Biotechnol., 2006, 124(1), 128-145.
22. Denisov, I.G.; Makris, T.M.; Sligar, S.G.; Schlichting, I. Structure and chemistry of cytochrome P450. Chem. Rev., 2005, 105, 2253-2277.
23. Urlacher, V.B.; Girhard, M. Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol., 2012, 30(1), 26-36.
24. Urlacher, V.B.; Lutz-Wahl, S.; Schmid, R.D. Microbial P450 enzymes in biotechnology. Appl. Microbiol. Biotechnol., 2004, 64(3), 317-325.
25. Gillam, E.M.J. Engineering cytochrome P450 enzymes. Chem. Res. Toxicol., 2007, 21(1), 220-231.
26. Lamb, D.C.; Waterman, M.R.; Kelly, S.L.; Guengerich, F.P. Cytochromes P450 and drug discovery. Curr. Opin. Biotechnol., 2007, 18(6), 504-512.
27. Guengerich, F.P. Cytochrome P450 and Chemical Toxicology. Chem. Res. Toxicol., 2007, 21(1), 70-83.
28. Ortiz de Montellano, P.R. Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes. Chem. Rev., 2009, 110(2), 932-948.
29. Martinez, C.A.; Stewart, J.D. Cytochrome P450s potential catalysts for asymmetric olefin epoxidations. Curr. Org. Chem., 2000, 4(3), 263-282.
30. Sligar, S.G.; Makris, T.M.; Denisov, I.G. Thirty years of microbial P450 monooxygenase research: peroxo-heme intermediates--the central bus station in heme oxygenase catalysis. Biochem. Biophys. Res. Commun., 2005, 338(1), 346-354.
31. Wienkers, L.C.; Heath, T.G. Predicting in vivo drug interactions from in vitro drug discovery data. Nat. Rev. Drug Discov., 2005, 4(10), 825-833.
32. Guengerich, F.P.; Rendic, S. Update Information on Drug Metabolism Systems 2009, Part I. Curr. Drug Metab., 2010, 11(1), 1-3.
33. Guengerich, F.P. Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. Drug Discov., 2002, 1(5), 359-366.
34. Guengerich, F.P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol., 2001, 14(6), 611-650.
35. Nelson, D.R. Progress in tracing the evolutionary paths of cytochrome P450. Biochim. Biophys. Acta Prot. Proteom., 2011, 1814(1), 14-18.
36. Hannemann, F.; Bichet, A.; Ewen, K.M.; Bernhardt, R. Cytochrome P450 systems-biological variations of electron transport chains. Biochim. Biophys. Acta, 2007, 1770(3), 330-344.
37. Munro, A.W.; Girvan, H.M.; McLean, K.J. Cytochrome P450-redox partner fusion enzymes. Biochim. Biophys. Acta, 2007, 1770(3), 345-359.
38. Guengerich, F.P.; Tang, Z.; Cheng, Q.; Salamanca-Pinzón, S.G. Approaches to deorphanization of human and microbial cytochrome P450 enzymes. Biochim. Biophys. Acta Prot. Proteom., 2011, 1814(1), 139-145.
39. Guengerich, F.P.; Tang, Z.; Salamanca-Pinzon, S.G.; Cheng, Q. Characterizing proteins of unknown function: orphan cytochrome p450 enzymes as a paradigm. Mol Interv, 2010, 10(3), 153-163.
40. Parikh, A.; Gillam, E.M.; Guengerich, F.P. Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol., 1997, 15(8), 784-788.
41. Kumar, S. Engineering cytochrome P450 biocatalysts for biotechnology, medicine and bioremediation. Expert Opin. Drug Metab. Tox., 2010, 6(2), 115-131.
42. Pflug, S.; Richter, S.M.; Urlacher, V.B. Development of a fedbatch process for the production of the cytochrome P450 monooxygenase CYP102A1 from Bacillus megaterium in E. coli. J. Biotechnol., 2007, 129(3), 481-488.
43. Rushmore, T.H.; Reider, P.J.; Slaughter, D.; Assang, C.; Shou, M. Bioreactor systems in drug metabolism: synthesis of cytochrome P450-generated metabolites. Metab. Eng., 2000, 2(2), 115-125.
44. Peters, F.T.; Dragan, C.A.; Schwaninger, A.E.; Sauer, C.; Zapp, J.; Bureik, M.; Maurer, H.H. Use of fission yeast heterologously expressing human cytochrome P450 2B6 in biotechnological synthesis of the designer drug metabolite N-(1-phenylcyclohexyl)-2-hydroxyethanamine. Forensic Sci. Int., 2009, 184(1-3), 69-73.
45. Jung, S.T.; Lauchli, R.; Arnold, F.H. Cytochrome P450: taming a wild type enzyme. Curr. Opin. Biotechnol., 2011. 22 (6), 809-817.
46. Fasan, R.; Meharenna, Y.T.; Snow, C.D.; Poulos, T.L.; Arnold, F.H. Evolutionary history of a specialized p450 propane monooxygenase. J. Mol. Biol., 2008, 383(5), 1069-1080.
47. Whitehouse, C.J.C.; Bell, S.G.; Wong, L.-L. P450BM3 (CYP102A1): connecting the dots. Chem. Soc. Rev., 2012, 41(3).
48. Eibl, R.; Eibl, D.; Pörtner, R.; Catapano, G.; Czermak, P.; Catapano, G.; Czermak, P.; Eibl, R.; Eibl, D.; Pörtner, R. Cell and Tissue Reaction Engineering. Springer Berlin Heidelberg: 2009; pp 173-259.
49. Cooney, C.L. Bioreactors: Design and Operation. Science, 1983, 219(4585), 728-733.
50. Santacoloma, P.A.; Sin, G.R.; Gernaey, K.V.; Woodley, J.M. Multienzyme-Catalyzed Processes: Next-Generation Biocatalysis. Org. Pro. Res. Dev., 2010, 15(1), 203-212.
51. Garcia-Ochoa, F.; Gomez, E. Bioreactor scale-up and oxygen transfer rate in microbial processes: An overview. Biotechnol. Adv., 2009, 27(2), 153-176.
52. Zöllner, A.; Buchheit, D.; Meyer, M.R.; Maurer, H.H.; Peters, F.T.; Bureik, M. Production of human phase 1 and 2 metabolites by whole-cell biotransformation with recombinant microbes. Bioanalysis, 2010, 2(7), 1277-1290.
53. Knight, V.; Sanglier, J.J.; DiTullio, D.; Braccili, S.; Bonner, P.; Waters, J.; Hughes, D.; Zhang, L. Diversifying microbial natural products for drug discovery. Appl. Microbiol. Biotechnol., 2003, 62(5), 446-458.
54. Fura, A.; Shu, Y.Z.; Zhu, M.; Hanson, R.L.; Roongta, V.; Humphreys, W.G. Discovering drugs through biological transformation: role of pharmacologically active metabolites in drug discovery. J. Med. Chem., 2004, 47(18), 4339-4351.
55. Griffini, P.; James, A.; Roberts, A.; Pellegatti, M. Metabolites in Safety Testing: Issues and Approaches to the Safety Evaluation of Human Metabolites in a Drug that is Extensively Metabolized. J. Drug Metabol. Toxicol., 1: 2157-7609
56. Nedderman, A.N.R. Metabolites in safety testing: metabolite identification strategies in discovery and development. Biopharm. Drug Dispos., 2009, 30 (4), 153-162.
57. Pirmohamed, M. Drug metabolism. Medicine, 2008, 36(7), 355-359.
58. Smith, R.V.; Rosazza, J.P. Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch. Biochem. Biophys., 1974, 161(2), 551-558.
59. Azerad, R. Microbial models for drug metabolism. Biotransformations, 1999, 169-218.
60. Venisetty, R.; Ciddi, V. Application of microbial biotransformation for the new drug discovery using natural drugs as substrates. Curr. Pharm. Biotechnol., 2003, 4(3), 153-167.
61. Asha, S.; Vidyavathi, M. Cunninghamella-A microbial model for drug metabolism studies-A review. Biotechnol. Adv., 2009, 27(1), 16-29.
62. Weis, R.; Winkler, M.; Schittmayer, M.; Kambourakis, S.; Vink, M.; Rozzell, J.D.; Glieder, A. A diversified library of bacterial and fungal bifunctional cytochrome P450 enzymes for drug metabolite synthesis. Adv. Synth. Catal., 2009, 351(13), 2140-2146.
63. Drǎgan, C.A.; Peters, F.T.; Bour, P.; Schwaninger, A.E.; Schaan, S.M.; Neunzig, I.; Widjaja, M.; Zapp, J.; Kraemer, T.; Maurer, H.H. Convenient Gram-Scale Metabolite Synthesis by Engineered Fission Yeast Strains Expressing Functional Human P450 Systems. Appl. Biochem. Biotechnol., 2011, 1-16.
64. Schroer, K.; Kittelmann, M.; Lütz, S. Recombinant human cytochrome P450 monooxygenases for drug metabolite synthesis. Biotechnol. Bioeng., 2010, 106(5), 699-706.
65. Sawayama, A.M.; Chen, M.M.; Kulanthaivel, P.; Kuo, M.S.; Hemmerle, H.; Arnold, F.H. A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds. Chemistry, 2009, 15(43), 11723-11729.
66. Rentmeister, A.; Brown, T.R.; Snow, C.D.; Carbone, M.N.; Arnold, F.H. Engineered Bacterial Mimics of Human Drug Metabolizing Enzyme CYP2C9. ChemCatChem, 2011, 3(6), 1065-1071.
67. Kumagai, H.; Umekita, M.; Sawa, R.; Takahashi, Y.; Arisawa, A.; Isshiki, K.; Nishimura, Y.; Akamatsu, Y. Generation of New Benanomicin Analogues by Biotransformation Using Escherichia coli Expressing Actinomycete Cytochrome P450. J. Antibiot., 2008, 61 (6), 394-399.
68. Klöckner, W.; Büchs, J. In Comprehensive Biotechnology (Second Edition). Editor-in-Chief: Murray, M.-Y. Ed.; Academic Press: Burlington, 2011, pp 213-226.
69. Falck, J.; Reddy, Y.K.; Haines, D.C.; Reddy, K.M.; Krishna, U.M.; Graham, S.; Murry, B.; Peterson, J.A. Practical, enantiospecific syntheses of 14, 15-EET and leukotoxin B (vernolic acid). Tetrahedron Lett., 2001, 42(25), 4131-4133.
70. Hanlon, S.P.; Friedberg, T.; Wolf, C.R.; Ghisalba, O.; Kittelmann, M. Recombinant yeast and bacteria that express human P450s: bioreactors for drug discovery, development, and biotechnology. Modern Biooxidation, 2007, 233-252.
71. Zhang, W.; Tang, W.L.; Wang, Z.; Li, Z. Regio-and Stereoselective Biohydroxylations with a Recombinant Escherichia coli Expressing P450pyr Monooxygenase of Sphingomonas Sp. HXN-200. Adv. Synth. Catal., 2010, 352(18), 3380-3390.
72. Pham, S.Q.; Gao, P.; Li, Z. Engineering of recombinant E. coli cells co-expressing P450pyrTM monooxygenase and glucose dehydrogenase for highly region-and stereoselective hydroxylation of alicycles with cofactor recycling. Biotechnol. Bioeng., 2012, 110 (2), 363-373
73. Sulistyaningdyah, W.T.; Ogawa, J.; Li, Q.S.; Maeda, C.; Yano, Y.; Schmid, R.D.; Shimizu, S. Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds. Appl. Microbiol. Biotechnol., 2005, 67(4), 556-562.
74. Landwehr, M.; Hochrein, L.; Otey, C.R.; Kasrayan, A.; Backvall, J.E.; Arnold, F.H. Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3. J. Am. Chem. Soc., 2006, 128(18), 6058-6059.
75. Whitehouse, C.J.C.; Yang, W.; Yorke, J.A.; Tufton, H.G.; Ogilvie, L.C.I.; Bell, S.G.; Zhou, W.; Bartlam, M.; Rao, Z.; Wong, L.L. Structure, electronic properties and catalytic behaviour of an activity-enhancing CYP102A1 (P450BM3) variant. Dalton Trans., 2011, 40(40), 10383-10396.
76. Dubey, K.K.; Haque, S.; Jawed, A.; Singh, B.P.; Behera, B. Construction of recombinant Escherichia coli for enhanced bioconversion of colchicine into 3-demethylated colchicine at 70l bioreactor level. Process Biochem., 2010, 45(7), 1036-1042.
77. Maurer, S.C.; Kühnel, K.; Kaysser, L.A.; Eiben, S.; Schmid, R.D.; Urlacher, V.B. Catalytic Hydroxylation in Biphasic Systems using CYP102A1 Mutants. Adv. Synth. Catal., 2005, 347(7-8), 1090-1098.
78. Vail, R.B.; Homann, M.J.; Hanna, I.; Zaks, A. Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli. J. Ind. Microbiol. Biotechnol., 2005, 32(2), 67-74.
79. Çelik, A.; Sperandio, D.; Speight, R.E.; Turner, N.J. Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450BM3 from Bacillus megaterium. Org. Biomol. Chem., 2005, 3(15), 2688-2690.
80. Peters, F.T.; Dragan, C.A.; Wilde, D.R.; Meyer, M.R.; Zapp, J.; Bureik, M.; Maurer, H.H. Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4'-hydroxymethyl-[alpha]-pyrrolidinobutyrophenone. Biochem. Pharmacol., 2007, 74(3), 511-520.
81. Gudiminchi, R.K.; Randall, C.; Opperman, D.J.; Olaofe, O.A.; Harrison, S.T.L.; Albertyn, J.; Smit, M.S. Whole-cell hydroxylation of n-octane by Escherichia coli strains expressing the CYP153A6 operon. Appl. Microbiol. Biotechnol., 2012, 1-10.
82. Schewe, H.; Holtmann, D.; Schrader, J. P450 BM-3-catalyzed whole-cell biotransformation of α-pinene with recombinant Escherichia coli in an aqueous-organic two-phase system. Appl. Microbiol. Biotechnol., 2009, 83(5), 849-857.
83. Otey, C.R.; Bandara, G.; Lalonde, J.; Takahashi, K.; Arnold, F.H. Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450. Biotechnol. Bioeng., 2006, 93(3), 494-499.
84. Hakki, T.; Zearo, S.; Drǎgan, C.-A.; Bureik, M.; Bernhardt, R. Coexpression of redox partners increases the hydrocortisone (cortisol) production efficiency in CYP11B1 expressing fission yeast Schizosaccharomyces pombe. J. Biotechnol., 2008, 133(3), 351-359.
85. Barnes, H.J.; Arlotto, M.P.; Waterman, M.R. Expression and enzymatic activity of recombinant cytochrome P450 17 alphahydroxylase in Escherichia coli. Proc. Natl. Acad. Sci. U. S. A., 1991, 88(13), 5597-5601.
86. Hunter, D.; Behrendorff, J.; Johnston, W.; Hayes, P.; Huang, W.; Bonn, B.; Hayes, M.; De Voss, J.; Gillam, E. Facile production of minor metabolites for drug development using a CYP3A shuffled library. Metab. Eng., 2011, 13 (6), 682-693
87. Kumar, S.; Sun, L.; Liu, H.; Muralidhara, B.; Halpert, J.R. Engineering mammalian cytochrome P450 2B1 by directed evolution for enhanced catalytic tolerance to temperature and dimethyl sulfoxide. Protein Eng. Des. Sel., 2006, 19(12), 547-554.
88. Huang, W.; Johnston, W.A.; Hayes, M.A.; De Voss, J.J.; Gillam, E.M.J. A shuffled CYP2C library with a high degree of structural integrity and functional versatility. Arch. Biochem. Biophys., 2007, 467(2), 193-205.
89. Tsai, R.; Yu, C.; Gunsalus, I.; Peisach, J.; Blumberg, W.; Orme-Johnson, W.; Beinert, H. Spin-state changes in cytochrome P-450cam on binding of specific substrates. Proc. Natl. Acad. Sci. USA., 1970, 66(4), 1157-1163.
90. Poulos, T.L.; Finzel, B.C.; Howard, A.J. High-resolution crystal structure of cytochrome P450cam. J. Mol. Biol., 1987, 195(3), 687-700.
91. Atkins, W.M.; Sligar, S.G. The roles of active site hydrogen bonding in cytochrome P-450cam as revealed by site-directed mutagenesis. J. Biol. Chem., 1988, 263(35), 18842-18849.
92. Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A.M.; Maves, S.A.; Benson, D.E.; Sweet, R.M.; Ringe, D.; Petsko, G.A.; Sligar, S.G. The catalytic pathway of cytochrome P450cam at atomic resolution. Science, 2000, 287(5458), 1615-1622.
93. De Voss, J.J.; Ortiz de Montellano, P.R. Computer-assisted, structure-based prediction of substrates for cytochrome P450cam. J. Am. Chem. Soc., 1995, 117(14), 4185-4186.
94. De Voss, J.J.; Sibbesen, O.; Zhang, Z.; de Montellano, P.R.O. Substrate docking algorithms and prediction of the substrate specificity of cytochrome P450cam and its L244A mutant. J. Am. Chem. Soc., 1997, 119(24), 5489-5498.
95. Zhang, Z.; Sibbesen, O.; Johnson, R.A.; Ortiz de Montellano, P.R. The substrate specificity of cytochrome P450cam. Biorg. Med. Chem., 1998, 6(9), 1501-1508.
96. Bell, S.G.; Harford-Cross, C.F.; Wong, L.L. Engineering the CYP101 system for in vivo oxidation of unnatural substrates. Protein Eng., 2001, 14(10), 797-802.
97. Stevenson, J.A.; Jones, J.P.; Wong, L.L. Mutations of phenylalanine 193 in the putative substrate access channel alter the substrate specificity of cytochrome P450cam. Isr. J. Chem., 2000, 40(1), 55-62.
98. Harford-Cross, C.F.; Carmichael, A.B.; Allan, F.K.; England, P.A.; Rouch, D.A.; Wong, L.L. Protein engineering of cytochrome P450cam (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Protein Eng., 2000, 13(2), 121-128.
99. England, P.A.; Harford-Cross, C.F.; Stevenson, J.-A.; Rouch, D.A.; Wong, L.-L. The oxidation of naphthalene and pyrene by cytochrome P450cam. FEBS Lett., 1998, 424(3), 271-274.
100. Bell, S.G.; Rouch, D.A.; Wong, L.-L. Selective aliphatic and aromatic carbon-hydrogen bond activation catalysed by mutants of cytochrome p450cam. J. Mol. Catal. B: Enzym., 1997, 3(6), 293-302.
101. Nickerson, D.P.; Harford-Cross, C.F.; Fulcher, S.R.; Wong, L.L. The catalytic activity of cytochrome P450cam towards styrene oxidation is increased by site-specific mutagenesis. FEBS Lett., 1997, 405(2), 153-156.
102. Kille, S.; Zilly, F.E.; Acevedo, J.P.; Reetz, M.T. Regio-and stereoselectivity of P450-catalysed hydroxylation of steroids controlled by laboratory evolution. Nat Chem, 2011, 3(9), 738-743.
103. Urlacher, V.B.; Bell, S.G.; Wong, L.L. The Bacterial Cytochrome P450 Monooxygenases: P450cam and P450BM-3. Modern Biooxidation, 2007, 99-122.
104. Kim, D.; Ortiz de Montellano, P.R. Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. Biotechnol. Lett, 2009, 31(9), 1427-1431.
105. Mouri, T.; Michizoe, J.; Ichinose, H.; Kamiya, N.; Goto, M. A recombinant Escherichia coli whole cell biocatalyst harboring a cytochrome P450cam monooxygenase system coupled with enzymatic cofactor regeneration. Appl. Microbiol. Biotechnol., 2006, 72(3), 514-520.
106. Yun, C.H.; Kim, K.H.; Kim, D.H.; Jung, H.C.; Pan, J.G. The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol., 2007, 25(7), 289-298.
107. Peters, M.W.; Meinhold, P.; Glieder, A.; Arnold, F.H. Regio-and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3. J. Am. Chem. Soc., 2003, 125(44), 13442-13450.
108. Dietrich, J.A.; Yoshikuni, Y.; Fisher, K.J.; Woolard, F.X.; Ockey, D.; McPhee, D.J.; Renninger, N.S.; Chang, M.C.; Baker, D.; Keasling, J.D. A novel semi-biosynthetic route for artemisinin production using engineered substrate-promiscuous P450(BM3). ACS Chem Biol, 2009, 4(4), 261-267.
109. Reetz, M.T. Laboratory evolution of stereoselective enzymes as a means to expand the toolbox of organic chemists. Tetrahedron, 2012, 68, 7530-7548.
110. Zilly, F.E.; Acevedo, J.P.; Augustyniak, W.; Deege, A.; Häusig, U.W.; Reetz, M.T. Tuning a P450 Enzyme for Methane Oxidation. Angew. Chem., 2011, 123(12), 2772-2776.
111. Li, Z.; Chang, D. Recent advances in regio-and stereoselective biohydroxylation of non-activated carbon atoms. Curr. Org. Chem., 2004, 8(17), 1647-1658.
112. Van Beilen, J.B.; Funhoff, E.G.; Van Loon, A.; Just, A.; Kaysser, L.; Bouza, M.; Holtackers, R.; Röthlisberger, M.; Li, Z.; Witholt, B. Cytochrome P450 alkane hydroxylases of the CYP153 family are common in alkane-degrading eubacteria lacking integral membrane alkane hydroxylases. Appl. Environ. Microbiol., 2006, 72(1), 59-65.
113. Li, Z.; Feiten, H.J.; van Beilen, J.B.; Duetz, W.; Witholt, B. Preparation of optically active N-benzyl-3-hydroxypyrrolidine by enzymatic hydroxylation. Tetrahedron: Asymmetry, 1999, 10(7), 1323-1333.
114. Chang, D.; Witholt, B.; Li, Z. Preparation of (S)-N-Substituted 4-Hydroxy-pyrrolidin-2-ones by Regio-and Stereoselective Hydroxylation with Sphingomonas sp. HXN-200. Org. Lett., 2000, 2(24), 3949-3952.
115. Li, Z.; Feiten, H.J.; Chang, D.; Duetz, W.A.; van Beilen, J.B.; Witholt, B. Preparation of (R)-and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio-and stereoselective, and easy to handle biocatalyst. J. Org. Chem., 2001, 66(25), 8424-8430.
116. Chang, D.; Feiten, H.J.; Engesser, K.H.; van Beilen, J.B.; Witholt, B.; Li, Z. Practical syntheses of N-substituted 3-hydroxyazetidines and 4-hydroxypiperidines by hydroxylation with Sphingomonas sp. HXN-200. Org. Lett., 2002, 4(11), 1859-1862.
117. Chang, D.; Heringa, M.F.; Witholt, B.; Li, Z. Enantioselective Trans Dihydroxylation of Nonactivated CC Double Bonds of Aliphatic Heterocycles with Sphingomonas sp. HXN-200. J. Org. Chem., 2003, 68(22), 8599-8606.
118. Funhoff, E.G.; Salzmann, J.; Bauer, U.; Witholt, B.; van Beilen, J.B. Hydroxylation and epoxidation reactions catalyzed by CYP153 enzymes. Enzyme Microb. Technol., 2007, 40(4), 806-812.
119. Funhoff, E.G.; Bauer, U.; García-Rubio, I.; Witholt, B.; Van Beilen, J.B. CYP153A6, a soluble P450 oxygenase catalyzing terminal-alkane hydroxylation. J. Bacteriol., 2006, 188(14), 5220-5227.
120. Zhu, D.; Seo, M.J.; Ikeda, H.; Cane, D.E. Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone. J. Am. Chem. Soc., 2011, 133(7), 2128-2131.
121. Prior, J.E.; Shokati, T.; Christians, U.; Gill, R.T. Identification and characterization of a bacterial cytochrome P450 for the metabolism of diclofenac. Appl. Microbiol. Biotechnol., 2010, 85(3), 625-633.
122. Kim, D.; Yukl, E.T.; Moenne-Loccoz, P.; Montellano, P.R. Fungal heme oxygenases: Functional expression and characterization of Hmx1 from Saccharomyces cerevisiae and CaHmx1 from Candida albicans. Biochemistry, 2006, 45(49), 14772-14780.
123. Schallmey, A.; den Besten, G.; Teune, I.G.; Kembaren, R.F.; Janssen, D.B. Characterization of cytochrome P450 monooxygenase CYP154H1 from the thermophilic soil bacterium Thermobifida fusca. Appl. Microbiol. Biotechnol., 2011, 89(5), 1475-1485.
124. Scheps, D.; Malca, S.H.; Hoffmann, H.; Nestl, B.M.; Hauer, B. Regioselective omega-hydroxylation of medium-chain n-alkanes and primary alcohols by CYP153 enzymes from Mycobacterium marinum and Polaromonas sp. strain JS666. Org Biomol Chem, 2011, 9(19), 6727-6733.
125. Girhard, M.; Machida, K.; Itoh, M.; Schmid, R.D.; Arisawa, A.; Urlacher, V.B. Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system. Microbial cell factories, 2009, 8, 36.
126. Chun, Y.J.; Shimada, T.; Waterman, M.R.; Guengerich, F.P. Understanding electron transport systems of Streptomyces cytochrome P450. Biochem. Soc. Trans., 2006, 34(Pt 6), 1183-1185.
127. Ewen, K.M.; Ringle, M.; Bernhardt, R. Adrenodoxin-A versatile ferredoxin. IUBMB Life, 2012, 64(6), 506-512.
128. Jenkins, C.M.; Waterman, M.R. Flavodoxin and NADPHflavodoxin reductase from Escherichia coli support bovine cytochrome P450c17 hydroxylase activities. J. Biol. Chem., 1994, 269(44), 27401-27408.
129. Girhard, M.; Tieves, F.; Weber, E.; Smit, M.; Urlacher, V. Cytochrome P450 reductase from Candida apicola: versatile redox partner for bacterial P450s. Appl. Microbiol. Biotechnol., 2012, 1-11.
130. Girhard, M.; Klaus, T.; Khatri, Y.; Bernhardt, R.; Urlacher, V. Characterization of the versatile monooxygenase CYP109B1 from Bacillus subtilis. Appl. Microbiol. Biotechnol., 2010, 87(2), 595-607.
131. Furuya, T.; Arai, Y.; Kino, K. Biotechnological Production of Caffeic Acid by Bacterial Cytochrome P450 CYP199A2. Appl. Environ. Microbiol., 2012, 78 (17), 6087-6094
132. Kitazume, T.; Tanaka, A.; Takaya, N.; Nakamura, A.; Matsuyama, S.; Suzuki, T.; Shoun, H. Kinetic analysis of hydroxylation of saturated fatty acids by recombinant P450foxy produced by an Escherichia coli expression system. Eur. J. Biochem., 2002, 269(8), 2075-2082.
133. Warman, A.J.; Robinson, J.W.; Luciakova, D.; Lawrence, A.D.; Marshall, K.R.; Warren, M.J.; Cheesman, M.R.; Rigby, S.E.J.; Munro, A.W.; McLean, K.J. Characterization of Cupriavidus metallidurans CYP116B1-A thiocarbamate herbicide oxygenating P450-phthalate dioxygenase reductase fusion protein. FEBS J., 2012, 279(9), 1675-1693.
134. Ichinose, H.; Wariishi, H. Heterologous expression and mechanistic investigation of a fungal cytochrome P450 (CYP5150A2): involvement of alternative redox partners. Arch. Biochem. Biophys., 2012, 518(1), 8-15.
135. Yu, F.; Okamoto, S.; Harada, H.; Yamasaki, K.; Misawa, N.; Utsumi, R. Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis. Cell. Mol. Life Sci., 2011, 68(6), 1033-1040.
136. Takamatsu, S.; Xu, L.H.; Fushinobu, S.; Shoun, H.; Komatsu, M.; Cane, D.E.; Ikeda, H. Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV-7469) of Streptomyces avermitilis. J. Antibiot. 2011, 64(1), 65-71.
137. Niraula, N.P.; Kanth, B.K.; Sohng, J.K.; Oh, T.J. Hydrogen peroxide-mediated dealkylation of 7-ethoxycoumarin by cytochrome P450 (CYP107AJ1) from Streptomyces peucetius ATCC27952. Enzyme Microb. Technol., 2011, 48(2), 181-186.
138. Choi, K.Y.; Jung, E.; Jung, D.H.; Pandey, B.P.; Yun, H.; Park, H.Y.; Kazlauskas, R.J.; Kim, B.G. Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. FEBS J., 2011, 279(1650-62).
139. Bell, S.G.; Yang, W.; Yorke, J.A.; Zhou, W.; Wang, H.; Harmer, J.; Copley, R.; Zhang, A.; Zhou, R.; Bartlam, M. Structure and function of CYP108D1 from Novosphingobium aromaticivorans DSM12444: an aromatic hydrocarbon-binding P450 enzyme. Acta Crystallogr. Sect. D. Biol. Crystallogr., 2012, 68(3), 277-291.
140. Morrone, D.; Chen, X.; Coates, R.M.; Peters, R.J. Characterization of the kaurene oxidase CYP701A3, a multifunctional cytochrome P450 from gibberellin biosynthesis. The Biochemical journal, 2010, 431(3), 337-344.
141. Zhou, Y.; Minami, T.; Honda, K.; Omasa, T.; Ohtake, H. Enhancement of recombinant enzyme activity in cpxA-deficient mutant of Escherichia coli. J. Biosci. Bioeng., 2010, 110(4), 403-407.
142. Sakaki, T.; Sugimoto, H.; Hayashi, K.; Yasuda, K.; Munetsuna, E.; Kamakura, M.; Ikushiro, S.; Shiro, Y. Bioconversion of vitamin D to its active form by bacterial or mammalian cytochrome P450. Biochim. Biophys. Acta Prot. s Proteom., 2011, 1814(1), 249-256.
143. Kudo, F.; Motegi, A.; Mizoue, K.; Eguchi, T. Cloning and Characterization of the Biosynthetic Gene Cluster of 16-Membered Macrolide Antibiotic FD-891: Involvement of a Dual Functional Cytochrome P450 Monooxygenase Catalyzing Epoxidation and Hydroxylation. ChemBioChem, 2010, 11(11), 1574-1582.
144. Kharel, M.K.; Nybo, S.E.; Shepherd, M.D.; Rohr, J. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters. ChemBioChem, 2010, 11(4), 523-532.
145. Kabumoto, H.; Miyazaki, K.; Arisawa, A. Directed Evolution of the Actinomycete Cytochrome P450 MoxA (CYP105) for Enhanced Activity. Biosci. Biotechnol. Biochem., 2009, 73(9), 1922-1927.
146. Anzai, Y.; Tsukada, S.; Sakai, A.; Masuda, R.; Harada, C.; Domeki, A.; Li, S.; Kinoshita, K.; Sherman, D.H.; Kato, F. Function of Cytochrome P450 Enzymes MycCI and MycG in Micromonospora griseorubida, a Producer of the Macrolide Antibiotic Mycinamicin. Antimicrob. Agents Chemother., 2012, 56(7), 3648-3656.
147. Osorio-Lozada, A.; Surapaneni, S.; Skiles, G.L.; Subramanian, R. Biosynthesis of drug metabolites using microbes in hollow fiber cartridge reactors: case study of diclofenac metabolism by Actinoplanes species. Drug Metab. Disposition, 2008, 36(2), 234-240.
148. Lisowska, K.; Szemraj, J.; Różalska, S.; Dłügoski, J. The expression of cytochrome P-450 and cytochrome P-450 reductase genes in the simultaneous transformation of corticosteroids and phenanthrene by Cunninghamella elegans. FEMS Microbiol. Lett., 2006, 261(2), 175-180.
149. Wang, R.F.; Cao, W.W.; Khan, A.A.; Cerniglia, C.E. Cloning, sequencing, and expression in Escherichia coli of a cytochrome P450 gene from Cunninghamella elegans. FEMS Microbiol. Lett., 2000, 188(1), 55-61.
150. Yadav, J.S.; Loper, J.C. Cloning and characterization of the cytochrome P450 oxidoreductase gene from the zygomycete fungus Cunninghamella. Biochem. Biophys. Res. Commun., 2000, 268(2), 345-353.
151. Pedrini, N.; Zhang, S.; Juárez, M.P.; Keyhani, N.O. Molecular characterization and expression analysis of a suite of cytochrome P450 enzymes implicated in insect hydrocarbon degradation in the entomopathogenic fungus Beauveria bassiana. Microbiology, 2010, 156(8), 2549-2557.
152. Xu, Y.; Orozco, R.; Kithsiri Wijeratne, E.M.; Espinosa-Artiles, P.; Leslie Gunatilaka, A.A.; Patricia Stock, S.; Molnár, I. Biosynthesis of the cyclooligomer depsipeptide bassianolide, an insecticidal virulence factor of Beauveria bassiana. Fungal Genet. Biol., 2009, 46(5), 353-364.
153. Petrič, Š.; Hakki, T.; Bernhardt, R.; Žigon, D.; Črešnar, B. Discovery of a steroid 11α-hydroxylase from Rhizopus oryzae and its biotechnological application. J. Biotechnol., 2010, 150(3), 428-437.
154. O'Callaghan, J.; Stapleton, P.C.; Dobson, A.D.W. Ochratoxin A biosynthetic genes in Aspergillus ochraceus are differentially regulated by pH and nutritional stimuli. Fungal Genet. Biol., 2006, 43(4), 213-221.
155. Kelly, D.E.; Krasevec, N.; Mullins, J.; Nelson, D.R. The CYPome (cytochrome P450 complement) of Aspergillus nidulans. Fungal Genet. Biol., 2009, 46(1), S53-S61.
156. Chen, K.; Tong, W.-Y.; Wei, D.-Z.; Jiang, W. The 11β-hydroxylation of 16,17β-epoxyprogesterone and the purification of the 11β-hydroxylase from Absidia coerulea IBL02. Enzyme Microb. Technol., 2007, 41(1-2), 71-79.
157. Park, H.-G.; Lim, Y.-R.; Eun, C.-Y.; Han, S.; Han, J.-S.; Cho, K.S.; Chun, Y.-J.; Kim, D. Candida albicans NADPH-P450 reductase: Expression, purification, and characterization of recombinant protein. Biochem. Biophys. Res. Commun., 2010, 396(2), 534-538.
158. Syed, K.; Yadav, J.S. P450 monooxygenases (P450ome) of the model white rot fungus Phanerochaete chrysosporium. Crit. Rev. Microbiol., 2012(38), 4, 339-363.
159. Lah, L.; Kraevec, N.; Trontelj, P.; Komel, R. High diversity and complex evolution of fungal cytochrome P450 reductase: Cytochrome P450 systems. Fungal Genet. Biol., 2008, 45(4), 446-458.
160. Makovec, T.; Breskvar, K. Catalytic and immunochemical properties of NADPH-cytochrome P450 reductase from fungus Rhizopus nigricans. J. Steroid Biochem. Mol. Biol., 2002, 82(1), 89-96.
161. Degregorio, D.; Sadeghi, S.J.; Di Nardo, G.; Gilardi, G.; Solinas, S.P. Understanding uncoupling in the multiredox centre P450 3A4-BMR model system. J. Biol. Inorg. Chem., 2011, 1-8.
162. Kadkhodayan, S.; Coulter, E.D.; Maryniak, D.M.; Bryson, T.A.; Dawson, J.H. Uncoupling oxygen transfer and electron transfer in the oxygenation of camphor analogues by cytochrome P450-CAM. J. Biol. Chem., 1995, 270(47), 28042-28048.
163. Carver, T.E.; Brantley Jr, R.E.; Singleton, E.; Arduini, R.; Quillin, M.L.; Phillips Jr, G.N.; Olson, J. A novel site-directed mutant of myoglobin with an unusually high O2 affinity and low autooxidation rate. J. Biol. Chem., 1992, 267(20), 14443-14450.
164. Reed, J.R.; Backes, W.L. Formation of P450• P450 Complexes and Their Effect on P450 Function. Pharmacol. Ther., 2011, 133 (3), 299-310
165. Chen, M.M.Y.; Snow, C.D.; Vizcarra, C.L.; Mayo, S.L.; Arnold, F.H. Comparison of random mutagenesis and semi-rational designed libraries for improved cytochrome P450 BM3-catalyzed hydroxylation of small alkanes. Protein Eng. Des. Sel., 2012, 25 (4), 171-178
166. Seifert, A.; Pleiss, J. Identification of Selectivity Determinants in CYP Monooxygenases by Modelling and Systematic Analysis of Sequence and Structure. Curr. Drug Metab., 2012, 13(2), 197-202.
167. Migita, C.T.; Matera, K.M.; Ikeda-Saito, M.; Olson, J.S.; Fujii, H.; Yoshimura, T.; Zhou, H.; Yoshida, T. The oxygen and carbon monoxide reactions of heme oxygenase. J. Biol. Chem., 1998, 273(2), 945-949.
168. Kenaan, C.; Zhang, H.; Shea, E.V.; Hollenberg, P.F. Uncovering the Role of Hydrophobic Residues in Cytochrome P450-Cytochrome P450 Reductase Interactions. Biochemistry, 2011, 50 (19), 3957-3967
169. Salazar, O.; Cirino, P.C.; Arnold, F.H. Thermostabilization of a cytochrome p450 peroxygenase. ChemBioChem, 2003, 4(9), 891-893.
170. Cirino, P.C.; Arnold, F.H. Regioselectivity and activity of cytochrome P450 BM-3 and mutant F87A in reactions driven by hydrogen peroxide. Adv. Synth. Catal., 2002, 344(9), 932-937.
171. Geng, M.; Duan, Z. Prediction of oxygen solubility in pure water and brines up to high temperatures and pressures. Geochim. Cosmochim. Acta, 2010, 74(19), 5631-5640.
172. Fritzsche, C. Degradation of pyrene at low defined oxygen concentrations by a Mycobacterium sp. Appl. Environ. Microbiol., 1994, 60(5), 1687-1689.
173. Özbek, B.; Gayik, S. The studies on the oxygen mass transfer coefficient in a bioreactor. Process Biochem., 2001, 36(8-9), 729-741.
174. Quijano, G.; Revah, S.; Gutiérrez-Rojas, M.; Flores-Cotera, L.B.; Thalasso, F. Oxygen transfer in three-phase airlift and stirred tank reactors using silicone oil as transfer vector. Process Biochem., 2009, 44(6), 619-624.
175. Jianlong, W. Enhancement of citric acid production by Aspergillus niger using n-dodecane as an oxygen-vector. Process Biochem., 2000, 35(10), 1079-1083.
176. Bae, J.-W.; Doo, E.-H.; Shin, S.-H.; Lee, S.-G.; Jeong, Y.-J.; Park, J.-B.; Park, S. Development of a recombinant Escherichia colibased biocatalyst to enable high styrene epoxidation activity with high product yield on energy source. Process Biochem., 2010, 45(2), 147-152.
177. Zhao, J.; Auclair, K. The activity of human CYP2D6 in low water organic solvents. Biotechnol. Bioeng., 2009, 102(4), 1268-1272.
178. Chefson, A.; Auclair, K. CYP3A4 Activity in the Presence of Organic Cosolvents, Ionic Liquids, or Water-Immiscible Organic Solvents. ChemBioChem, 2007, 8(10), 1189-1197.
179. Wong, T.S.; Arnold, F.H.; Schwaneberg, U. Laboratory evolution of cytochrome p450 BM-3 monooxygenase for organic cosolvents. Biotechnol. Bioeng., 2004, 85(3), 351-358.
180. Chauret, N.; Gauthier, A.; Nicoll-Griffith, D.A. Effect of Common Organic Solvents on in VitroCytochrome P450-Mediated Metabolic Activities in Human Liver Microsomes. Drug Metab. Disposition, 1998, 26(1), 1-4.
181. Hickman, D.; Wang, J.P.; Wang, Y.; Unadkat, J.D. Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab. Disposition, 1998, 26(3), 207-215.
182. Busby Jr, W.F.; Ackermann, J.M.; Crespi, C.L. Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. Drug Metab. Disposition, 1999, 27(2), 246-249.
183. Baldwin, C.V.F.; Wohlgemuth, R.; Woodley, J.M. The first 200-L scale asymmetric Baeyer Villiger oxidation using a whole-cell biocatalyst. Org. Process Res. Dev., 2008, 12(4), 660-665.
184. Ishikawa, M.; Yoshii, H.; Furuta, T. Interaction of modified cyclodextrins with cytochrome P-450. Biosci. Biotechnol. Biochem., 2005, 69(1), 246-248.
185. Hara, M.; Iazvovskaia, S.; Ohkawa, H.; Asada, Y.; Miyake, J. Immobilization of P450 monooxygenase and chloroplast for use in light-driven bioreactors. J. Biosci. Bioeng., 1999, 87(6), 793-797.
186. Fernandez-Salguero, P.; Gutierrez-Merino, C.; Bunch, A. Effect of immobilization on the activity of rat hepatic microsomal cytochrome P450 enzymes. Enzyme Microb. Technol., 1993, 15(2), 100-104.
187. Tanvir, S.; Pantigny, J.; Boulnois, P.; Pulvin, S. Covalent immobilization of recombinant human cytochrome CYP2E1 and glucose-6-phosphate dehydrogenase in alumina membrane for drug screening applications. J. Membr. Sci., 2009, 329(1), 85-90.
188. Tanvir, S.; Pantigny, J.; Morandat, S.; Pulvin, S. Development of immobilization technique for liver microsomes. Colloids Surf. B. Biointerfaces, 2009, 68(2), 178-183.
189. Maurer, S.C.; Schulze, H.; Schmid, R.D.; Urlacher, V. Immobilisation of P450 BM-3 and an NADP+ Cofactor Recycling System: Towards a Technical Application of Heme-Containing Monooxygenases in Fine Chemical Synthesis. Adv. Synth. Catal., 2003, 345(6-7), 802-810.
190. Waibel, M.; Schulze, H.; Huber, N.; Bachmann, T.T. Screenprinted bienzymatic sensor based on sol-gel immobilized Nippostrongylus brasiliensis acetylcholinesterase and a cytochrome P450 BM-3 (CYP102-A1) mutant. Biosens. Bioelectron., 2006, 21(7), 1132-1140.
191. Lu, Y.; Mei, L. Production of Indigo by Immobilization of E. coli BL21 (DE3) Cells in Calcium-Alginate Gel Capsules. Chin. J. Chem. Eng., 2007, 15(3), 387-390.
192. Weber, E.; Sirim, D.; Schreiber, T.; Thomas, B.; Pleiss, J.; Hunger, M.; Gläser, R.; Urlacher, V.B. Immobilization of P450 BM-3 monooxygenase on mesoporous molecular sieves with different pore diameters. J. Mol. Catal. B: Enzym., 2010, 64(1), 29-37.
193. Holtmann, D.; Mangold, K.-M.; Schrader, J. Entrapment of cytochrome P450 BM-3 in polypyrrole for electrochemically-driven biocatalysis. Biotechnol. Lett, 2009, 31(5), 765-770.
194. Matsumura, H.; Wiwatchaiwong, S.; Nakamura, N.; Yohda, M.; Ohno, H. A novel method for direct electrochemistry of a thermoacidophilic cytochrome P450. Electrochem. Commun., 2006, 8(8), 1245-1249.
195. Nicoli, R.; Bartolini, M.; Rudaz, S.; Andrisano, V.; Veuthey, J.L. Development of immobilized enzyme reactors based on human recombinant cytochrome P450 enzymes for phase I drug metabolism studies. J. Chromatogr. A, 2008, 1206(1), 2-10.
196. Zhao, L.; Güven, G.; Li, Y.; Schwaneberg, U. First steps towards a Zn/Co (III) sep-driven P450 BM3 reactor. Appl. Microbiol. Biotechnol., 2011, 1-11.
197. Hirakawa, H.; Nagamune, T. Molecular Assembly of P450 with Ferredoxin and Ferredoxin Reductase by Fusion to PCNA. ChemBioChem, 2010, 11(11), 1517-1520.
198. Oeda, K.; Sakaki, T.; Ohkawa, H. Expression of rat liver cytochrome P-450MC cDNA in Saccharomyces cerevisiae. DNA, 1985, 4(3), 203-210.
199. Pompon, D.; Louerat, B.; Bronine, A.; Urban, P. [6] Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol., 1996, 272, 51-64.
200. Dietrich, M.; Grundmann, L.; Kurr, K.; Valinotto, L.; Saussele, T.; Schmid, R.D.; Lange, S. Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. ChemBioChem, 2005, 6(11), 2014-2022.
201. Braun, A.; Geier, M.; Buehler, B.; Schmid, A.; Mauersberger, S.; Glieder, A. Steroid biotransformations in biphasic systems with Yarrowia lipolytica expressing human liver cytochrome P450 genes. Microbial cell factories, 2012, 11(1), 106.
202. Gonzalez, F.J.; Korzekwa, K.R. Cytochromes P450 expression systems. Annu. Rev. Pharmacool. Toxicol., 1995, 35(1), 369-390.
203. Peter Guengerich, F.; Brian, W.R.; Sari, M.A.; Ross, J.T. [14] Expression of mammalian cytochrome P450 enzymes using yeastbased vectors. Methods Enzymol., 1991, 206, 130-145.
204. Duan, H.; Schuler, M.A. Heterologous expression and strategies for encapsulation of membrane-localized plant P450s. Phytochem. Rev., 2006, 5(2), 507-523.
205. Bligh, H.F.; Wolf, C.R.; Smith, G.; Beggs, J.D. Production of cytochrome P450 reductase yeast-rat hybrid proteins in Saccharomyces cerevisiae. Gene, 1992, 110(1), 33-39.
206. Urban, P.; Mignotte, C.; Kazmaier, M.; Delorme, F.; Pompon, D. Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5. J. Biol. Chem., 1997, 272(31), 19176.
207. Hehn, A.; Morant, M.; Werck-Reichhart, D. Partial recoding of P450 and P450 reductase cDNAs for improved expression in yeast and plants. Methods Enzymol., 2002, 357, 343-351.
208. Dragan, C.A.; Zearo, S.; Hannemann, F.; Bernhardt, R.; Bureik, M. Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. FEMS Yeast Res., 2005, 5(6-7), 621-625.
209. Gregan, J.; Rabitsch, P.K.; Rumpf, C.; Novatchkova, M.; Schleiffer, A.; Nasmyth, K. High-throughput knockout screen in fission yeast. Nat Protoc, 2006, 1(5), 2457-2464.
210. Dahl Andersen, M.; Lindberg Møller, B. Use of methylotropic yeast Pichia, pastoris for expression of cytochromes P450. Methods Enzymol., 2002, 357, 333-342.
211. Geier, M.; Braun, A.; Emmerstorfer, A.; Pichler, H.; Glieder, A. Production of human cytochrome P450 2D6 drug metabolites with recombinant microbes-a comparative study. Biotechnology journal, 2012, 7 (11), 1346-1358
212. Shiningavamwe, A.; Obiero, G.; Albertyn, J.; Nicaud, J.M.; Smit, M. Heterologous expression of the benzoate para-hydroxylase encoding gene (CYP53B1) from Rhodotorula minuta by Yarrowia lipolytica. Appl. Microbiol. Biotechnol., 2006, 72(2), 323-329.
213. Nthangeni, M.; Urban, P.; Pompon, D.; Smit, M.; Nicaud, J.M. The use of Yarrowia lipolytica for the expression of human cytochrome P450 CYP1A1. Yeast, 2004, 21(7), 583-592.
214. Barnes, H.J. Maximizing expression of eukaryotic cytochrome P450s in Escherichia coli. Methods Enzymol., 1996, 272, 3-14.
215. Stark, K.; Dostalek, M.; Guengerich, F. Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide. FEBS J., 2008, 275(14), 3706-3717.
216. Wu, Z.L.; Bartleson, C.J.; Ham, A.J.; Guengerich, F.P. Heterologous expression, purification, and properties of human cytochrome P450 27C1. Arch. Biochem. Biophys., 2006, 445(1), 138-146.
217. Wu, Z.L.; Sohl, C.D.; Shimada, T.; Guengerich, F.P. Recombinant enzymes overexpressed in bacteria show broad catalytic specificity of human cytochrome P450 2W1 and limited activity of human cytochrome P450 2S1. Mol. Pharmacol., 2006, 69(6), 2007-2014.
218. Gillam, E.M.; Baba, T.; Kim, B.R.; Ohmori, S.; Guengerich, F.P. Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch. Biochem. Biophys., 1993, 305(1), 123-131.
219. Fisher, C.W.; Caudle, D.L.; Martin-Wixtrom, C.; Quattrochi, L.C.; Tukey, R.H.; Waterman, M.R.; Estabrook, R.W. High-level expression of functional human cytochrome P450 1A2 in Escherichia coli. FASEB J., 1992, 6(2), 759-764.
220. Tang, Z.; Salamanca-Pinzon, S.G.; Wu, Z.L.; Xiao, Y.; Guengerich, F.P. Human cytochrome P450 4F11: heterologous expression in bacteria, purification, and characterization of catalytic function. Arch. Biochem. Biophys., 2010, 494(1), 86-93.
221. Halkier, B.A.; Nielsen, H.L.; Koch, B.; Moller, B.L. Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli. Arch. Biochem. Biophys., 1995, 322(2), 369-377.
222. Kagawa, N.; Cao, Q.; Kusano, K. Expression of human aromatase (CYP19) in Escherichia coli by N-terminal replacement and induction of cold stress response. Steroids, 2003, 68(2), 205-209.
223. von Wachenfeldt, C.; Richardson, T.H.; Cosme, J.; Johnson, E.F. Microsomal P450 2C3 Is Expressed as a Soluble Dimer inEscherichia coliFollowing Modifications of Its N-terminus. Arch. Biochem. Biophys., 1997, 339(1), 107-114.
224. Cosme, J.; Johnson, E.F. Engineering microsomal cytochrome P450 2C5 to be a soluble, monomeric enzyme. J. Biol. Chem., 2000, 275(4), 2545.
225. Rawal, S.; Yip, S.S.; Coulombe, R.A. Jr., Cloning, expression and functional characterization of cytochrome P450 3A37 from turkey liver with high aflatoxin B1 epoxidation activity. Chem. Res. Toxicol., 2010, 23(8), 1322-1329.
226. Wu, Z.L.; Sohl, C.D.; Shimada, T.; Guengerich, F.P. Recombinant enzymes overexpressed in bacteria show broad catalytic specificity of human cytochrome P450 2W1 and limited activity of human cytochrome P450 2S1. Mol. Pharmacol., 2006, 69(6), 2007-2014.
227. Larson, J.R.; Coon, M.J.; Porter, T.D. Alcohol-inducible cytochrome P-450IIE1 lacking the hydrophobic NH2-terminal segment retains catalytic activity and is membrane-bound when expressed in Escherichia coli. J. Biol. Chem., 1991, 266(12), 7321-7324.
228. Li, Y.C.; Chiang, J.Y. The expression of a catalytically active cholesterol 7 alpha-hydroxylase cytochrome P450 in Escherichia coli. J. Biol. Chem., 1991, 266(29), 19186-19191.
229. Sandhu, P.; Baba, T.; Guengerich, F.P. Expression of modified cytochrome P450 2C10 (2C9) in Escherichia coli, purification, and reconstitution of catalytic activity. Arch. Biochem. Biophys., 1993, 306(2), 443-450.
230. Pritchard, M.P.; Ossetian, R.; Li, D.N.; Henderson, C.J.; Burchell, B.; Wolf, C.R.; Friedberg, T. A general strategy for the expression of recombinant human cytochrome P450s in Escherichia coli using bacterial signal peptides: expression of CYP3A4, CYP2A6, and CYP2E1. Arch. Biochem. Biophys., 1997, 345(2), 342-354.
231. Muller, P.; Warr, E.; Stevenson, B.J.; Pignatelli, P.M.; Morgan, J.C.; Steven, A.; Yawson, A.E.; Mitchell, S.N.; Ranson, H.; Hemingway, J.; Paine, M.J.; Donnelly, M.J. Field-caught permethrinresistant Anopheles gambiae overexpress CYP6P3, a P450 that metabolises pyrethroids. PLoS Genet., 2008, 4(11), e1000286.
232. Kagawa, N.; Cao, Q. Osmotic stress induced by carbohydrates enhances expression of foreign proteins in Escherichia coli. Arch. Biochem. Biophys., 2001, 393(2), 290-296.
233. Kusano, K.; Waterman, M.R.; Sakaguchi, M.; Omura, T.; Kagawa, N. Protein synthesis inhibitors and ethanol selectively enhance heterologous expression of P450s and related proteins in Escherichia coli. Arch. Biochem. Biophys., 1999, 367(1), 129-136.
234. Betiku, E. Molecular chaperones involved in Heterologous protein folding in Escherichia coli. Biotechnol. Rev., 2006, 12, 66-75.
235. Wu, Z.L.; Qiao, J.; Zhang, Z.G.; Guengerich, F.P.; Liu, Y.; Pei, X.Q. Enhanced bacterial expression of several mammalian cytochrome P450s by codon optimization and chaperone coexpression. Biotechnol. Lett, 2009, 31(10), 1589-1593.
236. Mitsuda, M.; Iwasaki, M. Improvement in the expression of CYP2B6 by co-expression with molecular chaperones GroES/EL in Escherichia coli. Protein Expr. Purif., 2006, 46(2), 401-405.
237. Rupasinghe, S.G.; Duan, H.; Frericks Schmidt, H.L.; Berthold, D.A.; Rienstra, C.M.; Schuler, M.A. High-yield expression and purification of isotopically labeled cytochrome P450 monooxygenases for solid-state NMR spectroscopy. Biochim. Biophys. Acta Biomembranes, 2007, 1768(12), 3061-3070.
238. Ahn, T.; Yang, S.; Yun, C.H. High-level expression of human cytochrome P450 1A2 by co-expression with human molecular chaperone HDJ-1 (Hsp40). Protein Expr. Purif., 2004, 36(1), 48-52.
239. Ahn, T.; Yun, C.H. High-level expression of human cytochrome P450 3A4 by co-expression with human molecular chaperone HDJ-1 (Hsp40). Arch. Pharmacal Res., 2004, 27(3), 319-323.
240. Kaewpa, D.; Boonsuepsakul, S.; Rongnoparut, P. Functional expression of mosquito NADPH-cytochrome P450 reductase in Escherichia coli. J. Econ. Entomol., 2007, 100(3), 946-953.
241. Andersen, J.F.; Utermohlen, J.G.; Feyereisen, R. Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in Escherichia coli and reconstitution of an insecticide-metabolizing P450 system. Biochemistry, 1994, 33(8), 2171-2177.
242. Hull, A.K.; Celenza, J.L. Bacterial expression and purification of the Arabidopsis NADPH-cytochrome P450 reductase ATR2. Protein Expr. Purif., 2000, 18(3), 310-315.
243. Gillam, E.M.J.; Baba, T.; Kim, B.; Ohmori, S.; Guengerich, F. Expression of Modified Human Cytochrome P450 3A4 in Escherichia coli and Purification and Reconstitution of the Enzyme. Arch. Biochem. Biophys., 1993, 305(1), 123-131.
244. Hansen, C.H.; Wittstock, U.; Olsen, C.E.; Hick, A.J.; Pickett, J.A.; Halkier, B.A. Cytochrome P450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. J. Biol. Chem., 2001, 276(14), 11078-11085.
245. Hull, A.K.; Vij, R.; Celenza, J.L. Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc. Natl. Acad. Sci. USA., 2000, 97(5), 2379-2384.
246. Wittstock, U.; Halkier, B.A. Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of Lphenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate. J. Biol. Chem., 2000, 275(19), 14659-14666.
247. Reed, J.R. The use of liposomes in the study of drug metabolism: a method to incorporate the enzymes of the cytochrome p450 monooxygenase system into phospholipid, bilayer vesicles. Methods Mol. Biol., 2010, 606, 11-20.
248. Grinkova, Y.V.; Denisov, I.G.; Sligar, S.G. Functional reconstitution of monomeric CYP3A4 with multiple cytochrome P450 reductase molecules in Nanodiscs. Biochem. Biophys. Res. Commun., 2010, 398(2), 194-198.
249. Fisher, C.W.; Shet, M.S.; Estabrook, R.W. [2] Construction of plasmids and expression in Escherichia coli of enzymatically active fusion proteins containing the heme-domain of a P450 linked to NADPH-P450 reductase. Methods Enzymol., 1996, 272, 15-25.
250. Leonard, E.; Yan, Y.; Koffas, M.A. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng., 2006, 8(2), 172-181.
251. Hotze, M.; Schroder, G.; Schroder, J. Cinnamate 4-hydroxylase from Catharanthus roseus, and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli. FEBS Lett., 1995, 374(3), 345-350.
252. Josephy, P.D.; Evans, D.H.; Parikh, A.; Guengerich, F.P. Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli. Chem. Res. Toxicol., 1998, 11(1), 70-74.
253. Iwata, H.; Fujita, K.; Kushida, H.; Suzuki, A.; Konno, Y.; Nakamura, K.; Fujino, A.; Kamataki, T. High catalytic activity of human cytochrome P450 co-expressed with human NADPHcytochrome P450 reductase in Escherichia coli. Biochem. Pharmacol., 1998, 55(8), 1315-1325.
254. Hansen, C.H.; Du, L.; Naur, P.; Olsen, C.E.; Axelsen, K.B.; Hick, A.J.; Pickett, J.A.; Halkier, B.A. CYP83b1 is the oximemetabolizing enzyme in the glucosinolate pathway in Arabidopsis. J. Biol. Chem., 2001, 276(27), 24790-24796.
255. Bak, S.; Kahn, R.A.; Olsen, C.E.; Halkier, B.A. Cloning and expression in Escherichia coli of the obtusifoliol 14α demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α demethylases (CYP51) from fungi and mammals. Plant J., 1997, 11(2), 191-201.
256. Bak, S.; Kahn, R.A.; Nielsen, H.L.; Møller, B.L.; Halkier, B.A. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol. Biol., 1998, 36(3), 393-405.
257. Saribas, A.S.; Gruenke, L.; Waskell, L. Overexpression and purification of the membrane-bound cytochrome P450 2B4. Protein Expr. Purif., 2001, 21(2), 303-309.
258. Davies, M.D.; Qin, L.; Beck, J.L.; Suslick, K.S.; Koga, H.; Horiuchi, T.; Sligar, S.G. Putidaredoxin reduction of cytochrome P-450cam: dependence of electron transfer on the identity of putidaredoxin's C-terminal amino acid. J. Am. Chem. Soc., 1990, 112(20), 7396-7398.
259. Sibbesen, O.; De Voss, J.J.; Montellano, P.R. Putidaredoxin reductase-putidaredoxin-cytochrome p450cam triple fusion protein. Construction of a self-sufficient Escherichia coli catalytic system. J. Biol. Chem., 1996, 271(37), 22462-22469.
260. Schwaneberg, U.; Schmidt-Dannert, C.; Schmitt, J.; Schmid, R.D. A Continuous Spectrophotometric Assay for P450 BM-3, a Fatty Acid Hydroxylating Enzyme, and Its Mutant F87A. Anal. Biochem., 1999, 269(2), 359-366.
261. Carmichael, A.B.; Wong, L.L. Protein engineering of Bacillus megaterium CYP102. Eur. J. Biochem., 2001, 268(10), 3117-3125.
262. Wen, L.P.; Fulco, A.J. Cloning of the gene encoding a catalytically self-sufficient cytochrome P-450 fatty acid monooxygenase induced by barbiturates in Bacillus megaterium and its functional expression and regulation in heterologous (Escherichia coli) and homologous (Bacillus megaterium) hosts. J. Biol. Chem., 1987, 262(14), 6676-6682.
263. Robin, A.; Roberts, G.A.; Kisch, J.; Sabbadin, F.; Grogan, G.; Bruce, N.; Turner, N.J.; Flitsch, S.L. Engineering and improvement of the efficiency of a chimeric [P450cam-RhFRed reductase domain] enzyme. Chem. Commun., 2009(18), 2478-2480.
264. Robin, A.; Köhler, V.; Jones, A.; Ali, A.; Kelly, P.P.; O'Reilly, E.; Turner, N.J.; Flitsch, S.L. Chimeric self-sufficient P450cam-RhFRed biocatalysts with broad substrate scope. Beilstein J. Org. Chem., 2011, 7, 1494-1498.
265. Li, S.; Podust, L.M.; Sherman, D.H. Engineering and analysis of a self-sufficient biosynthetic cytochrome P450 PikC fused to the RhFRED reductase domain. J. Am. Chem. Soc., 2007, 129(43), 12940-12941.
266. Nodate, M.; Kubota, M.; Misawa, N. Functional expression system for cytochrome P450 genes using the reductase domain of selfsufficient P450RhF from Rhodococcus sp. NCIMB 9784. Appl. Microbiol. Biotechnol., 2006, 71(4), 455-462.
267. Chenault, H.K.; Whitesides, G.M. Regeneration of nicotinamide cofactors for use in organic synthesis. Appl. Biochem. Biotechnol., 1987, 14(2), 147-197.
268. Chen, R.R. Permeability issues in whole-cell bioprocesses and cellular membrane engineering. Appl. Microbiol. Biotechnol., 2007, 74(4), 730-738.
269. Helander, I.I.M.; Alakomi, H.L.; Latva-Kala, K.; Koski, P. Polyethyleneimine is an effective permeabilizer of gram-negative bacteria. Microbiology, 1997, 143(10), 3193-3199.
270. Ni, Y.; Chen, R.R. Accelerating whole-cell biocatalysis by reducing outer membrane permeability barrier. Biotechnol. Bioeng., 2004, 87(6), 804-811.
271. Upadhya, R. Cell permeabilization-an approach to increase the biocatalysis in yeasts. Frontiers in Fungal Ecology, Diversity and Metabolites I. K. International Pub. House, 2009, 264-272.
272. Stojkovič, G.; Žnidaršič-Plazl, P. Continuous synthesis of L-malic acid using whole-cell microreactor. Process Biochem., 2012, 47, 1102-1107.
273. Sotirova, A.; Spasova, D.; Galabova, D.; Karpenko, E.; Shulga, A. Rhamnolipid-biosurfactant permeabilizing effects on gram-positive and gram-negative bacterial strains. Curr. Microbiol., 2008, 56(6), 639-644.
274. Stewart, J.D.; Reed, K.W.; Martinez, C.A.; Zhu, J.; Chen, G.; Kayser, M.M. Recombinant baker's yeast as a whole-cell catalyst for asymmetric Baeyer-Villiger oxidations. J. Am. Chem. Soc., 1998, 120(15), 3541-3548.
275. Weckbecker, A.; Gröger, H.; Hummel, W. Regeneration of nicotinamide coenzymes: principles and applications for the synthesis of chiral compounds. Biosystems Eng. I, 2010, 195-242.
276. Schewe, H.; Kaup, B.-A.; Schrader, J. Improvement of P450BM-3; whole-cell biocatalysis by integrating heterologous cofactor regeneration combining glucose facilitator and dehydrogenase in E. coli. Appl. Microbiol. Biotechnol., 2008, 78(1), 55-65.
277. Mouri, T.; Shimizu, T.; Kamiya, N.; Goto, M.; Ichinose, H. Design of a cytochrome P450BM3 reaction system linked by two-step cofactor regeneration catalyzed by a soluble transhydrogenase and glycerol dehydrogenase. Biotechnol. Prog., 2009, 25(5), 1372-1378.
278. Fasan, R.; Crook, N.C.; Peters, M.W.; Meinhold, P.; Buelter, T.; Landwehr, M.; Cirino, P.C.; Arnold, F.H. Improved product-perglucose yields in P450-dependent propane biotransformations using engineered Escherichia coli. Biotechnol. Bioeng., 2011, 108(3), 500-510.
279. Estabrook, R.W.; Faulkner, K.M.; Shet, M.S.; Fisher, C.W. [5] Application of electrochemistry for P450-catalyzed reactions. Methods Enzymol., 1996, 272, 44-51.
280. Reipa, V.; Mayhew, M.P.; Vilker, V.L. A direct electrode-driven P450 cycle for biocatalysis. Proc. Natl. Acad. Sci. USA. 1997, 94(25), 13554-13558.
281. Shumyantseva, V.; Bulko, T.; Kuznetsova, G.; Samenkova, N.; Archakov, A. Electrochemistry of cytochromes P450: Analysis of current-voltage characteristics of electrodes with immobilized cytochromes P450 for the screening of substrates and inhibitors. Biochemistry, 2009, 74(4), 438-444.
282. Sadeghi, S.J.; Fantuzzi, A.; Gilardi, G. Breakthrough in P450 bioelectrochemistry and future perspectives. Biochim. Biophys. Acta Prot. Proteom., 2011, 1814(1), 237-248.
283. Spolitak, T.; Funhoff, E.G.; Ballou, D.P. Spectroscopic studies of the oxidation of ferric CYP153A6 by peracids: Insights into P450 higher oxidation states. Arch. Biochem. Biophys., 2010, 493(2), 184-191.
284. Shoji, O.; Fujishiro, T.; Nagano, S.; Tanaka, S.; Hirose, T.; Shiro, Y.; Watanabe, Y. Understanding substrate misrecognition of hydrogen peroxide dependent cytochrome P450 from Bacillus subtilis. J. Biol. Inorg. Chem., 2010, 15(8), 1331-1339.
285. Shoji, O.; Fujishiro, T.; Nakajima, H.; Kim, M.; Nagano, S.; Shiro, Y.; Watanabe, Y. Hydrogen Peroxide Dependent Monooxygenations by Tricking the Substrate Recognition of Cytochrome P450BSβ. Angew. Chem. Int. Ed., 2007, 46(20), 3656-3659.
286. Woodley, J.M.; Bisschops, M.; Straathof, A.J.J.; Ottens, M. Future directions for in situ product removal (ISPR). J. Chem. Technol. Biotechnol., 2008, 83(2), 121-123.
287. Lye, G.J.; Woodley, J.M. Application of in situ product-removal techniques to biocatalytic processes. Trends Biotechnol., 1999, 17(10), 395-402.
288. Stark, D.; Von Stockar, U. In situ product removal (ISPR) in whole cell biotechnology during the last twenty years. Adv. Biochem. Eng. Biotechnol., 2003, 80, 149-175.
289. Vicenzi, J.T.; Zmijewski, M.J.; Reinhard, M.R.; Landen, B.E.; Muth, W.L.; Marler, P.G. Large-scale stereoselective enzymatic ketone reduction with in situ product removal via polymeric adsorbent resins. Enzyme Microb. Technol., 1997, 20(7), 494-499.
290. Buque-Taboada, E.M.; Straathof, A.J.J.; Heijnen, J.J.; Van der Wielen, L.A.M. In situ product removal using a crystallization loop in asymmetric reduction of 4-oxoisophorone by Saccharomyces cerevisiae. Biotechnol. Bioeng., 2004, 86(7), 795-800.
291. Alphand, V.; Carrea, G.; Wohlgemuth, R.; Furstoss, R.; Woodley, J.M. Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases. Trends Biotechnol., 2003, 21(7), 318-323.
292. Labinger, J.A.; Bercaw, J.E. Understanding and exploiting C-H bond activation. Nature, 2002, 417(6888), 507-514.
293. Wender, P.A.; Hilinski, M.K.; Mayweg, A.V.W. Late-Stage Intermolecular CH Activation for Lead Diversification: A Highly Chemoselective Oxyfunctionalization of the C-9 Position of Potent Bryostatin Analogues. Org. Lett., 2004, 7(1), 79-82.
294. Das, S.; Incarvito, C.D.; Crabtree, R.H.; Brudvig, G.W. Molecular recognition in the selective oxygenation of saturated CH bonds by a dimanganese catalyst. Science, 2006, 312(5782), 1941-1943.
295. Chen, M.S.; White, M.C. A Predictably Selective Aliphatic C-H Oxidation Reaction for Complex Molecule Synthesis. Science, 2007, 318(5851), 783-787.
296. Litvinas, N.D.; Brodsky, B.H.; Du Bois, J. C-H hydroxylation using a heterocyclic catalyst and aqueous H2O2. Angew. Chem. Int. Ed. Engl., 2009, 48(25), 4513-4516.
297. Stang, E.M.; Christina White, M. Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidation. Nat Chem, 2009, 1(7), 547-551.
298. McMurray, L.; O'Hara, F.; Gaunt, M.J. Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation. Chem. Soc. Rev., 2011, 40(4), 1885-1898.
299. Newhouse, T.; Baran, P.S. If C-H Bonds Could Talk: Selective C. H Bond Oxidation. Angew. Chem. Int. Ed., 2011, 50(15), 3362-3374.
300. Nakajima, H.; Osami, S.; Watanabe, Y. Molecular Design of Heme Proteins for Future Application. Catal. Surv. Asia, 2011, 15(2), 134-143.
301. Kiener, A. Enzymatic oxidation of methyl groups on aromatic heterocycles: a versatile method for the preparation of heteroaromatic carboxylic acids. Angew. Chem. Int. Ed. Eng., 1992, 31(6), 774-775.
302. Shibasaki, T.; Mori, H.; Ozaki, A. Enzymatic production of trans-4-hydroxy-L-proline by regio-and stereospecific hydroxylation of L-proline. Biosci. Biotechnol. Biochem., 2000, 64(4), 746-750.
303. Collins, A.M.; Woodley, J.M.; Liddell, J.M. Determination of reactor operation for the microbial hydroxylation of toluene in a two-liquid phase process. J. Ind. Microbiol. Biotechnol., 1995, 14(5), 382-388.
304. Han, G.H.; Bang, S.E.; Babu, B.K.; Chang, M.; Shin, H.-J.; Kim, S.W. Bio-indigo production in two different fermentation systems using recombinant Escherichia coli cells harboring a flavincontaining monooxygenase gene (fmo). Process Biochem., 2011, 46(3), 788-791.