Microbial P450 enzymes in biotechnology

Applied Microbiology and Biotechnology

Volumn 64, Issue 3, 2004, Pages 317-325

  Urlacher, V B ^a   Lutz Wahl, S ^b   Schmid, R D ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; CYTOCHROME P450; HEME; UNSPECIFIC MONOOXYGENASE; XENOBIOTIC AGENT;

BIOTECHNOLOGY;

BIOCATALYST; BIOTECHNOLOGY; CATALYSIS; CATALYST; DETOXIFICATION; ELECTRON TRANSPORT; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME ENGINEERING; ENZYME IMMOBILIZATION; ENZYME MECHANISM; ENZYME PURIFICATION; ENZYME STABILITY; ENZYME STRUCTURE; ENZYME SYNTHESIS; FERMENTATION TECHNIQUE; GENE SEQUENCE; HUMAN; HYDROPHOBICITY; NONHUMAN; OXIDATION; PROTEIN ENGINEERING; REGULATORY MECHANISM; SHORT SURVEY;

BACTERIA; BIOTECHNOLOGY; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME STABILITY; ENZYMES, IMMOBILIZED; NADP; OXIDATION-REDUCTION; PROTEIN ENGINEERING;

ALGAE; ANIMALIA; BACTERIA (MICROORGANISMS); FUNGI;

EID: 2442472003     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-003-1514-1     Document Type: Short Survey

References (97)

1. Aitio A (1978) A simple and sensitive assay of 7-ethoxycoumarin deethylation. Anal Biochem 85(2):488-491
2. Appel D, Lutz-Wahl S, Fischer P, Schwaneberg U, Schmid RD (2001) A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J Biotechnol 88(2):167-171
3. Atkins WM, Sligar SG (1988a) Deuterium isotope effects in norcamphor metabolism by cytochrome P-450cam: kinetic evidence for the two-electron reduction of a high-valent iron-oxo intermediate. Biochemistry 27(5):1610-1616
4. Atkins WM, Sligar SG (1988b) The roles of active site hydrogen bonding in cytochrome P-450cam as revealed by site-directed mutagenesis. J Biol Chem 263(35):11842-11849
5. Atkins WM, Sligar SG (1990) Tyrosine-96 as a natural spectroscopic probe of the cytochrome P-450cam active site. Biochemistry 29(5):1271-1275
6. Azari MR, Wiseman A (1980) Solubilization of cytochrome P450 in a high yield from Saccharomyces cerivisiae microsomal membrane: stabilization effect. Biochem Soc Trans 8:713-714
7. Bathelt C, Schmid RD, Pleiss J (2002) Regioselectivity of CYP2B6: homology modeling, molecular dynamics simulation, docking. J Mol Model 8:327-335
8. Bell SG, Harford-Cross CF, Wong LL (2001) Engineering the CYP101 system for in vivo oxidation of unnatural substrates. Protein Eng 14(10):797-802
9. Bell SG, Stevenson JA, Boyd HD, Campbell S, Riddle AD, Orton EL, Wong LL (2002) Butane and propane oxidation by engineered cytochrome P450cam. Chem Commun (Camb) 5:490-491
10. Bell SG, Chen X, Xu F, Rao Z, Wong LL (2003a) Engineering substrate recognition in catalysis by cytochrome P450cam. Biochem Soc Trans 31(3):558-562
11. Bell SG, Chen X, Sowden RJ, Xu F, Williams JN, Wong LL, Rao Z (2003b) Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam. J Am Chem Soc 125(3):705-714
12. Bezalel L, Hadar Y, Fu PP, Freeman JP, Cerniglia CE (1996) Metabolism of phenanthrene by the white rot fungus Pleurotus ostreatus. Appl Environ Microbiol 62(7):2247-2253
13. Black SD, Linger MH, Freck LC, Kazemi S, Galbraith JA (1994) Affinity isolation and characterization of cytochrome P450 102 (BM-3) from barbiturate-induced Bacillus megaterium. Arch Biochem Biophys 310(1):126-133
14. Boddupalli SS, Estabrook RW, Peterson JA (1990) Fatty acid monooxygenation by cytochrome P-450BM-3. J Biol Chem 265(8):4233-4239
15. Capdevila JH, Wei S, Helvig C, Falck JR, Belosludtsev Y, Truan G, Graham-Lorence SE, Peterson JA (1996) The highly stereoselective oxidation of polyunsaturated fatty acids by cytochrome P450BM-3. J Biol Chem 271(37):22663-22671
16. Carmichael AB, Wong LL (2001) Protein engineering of Bacillus megaterium CYP102. The oxidation of polycyclic aromatic hydrocarbons. Eur J Biochem 268(10):3117-3125
17. Cirino PC, Arnold FH (2002) Regioselectivity and activity of cytochrome P450 BM-3 and mutant F87A in reactions driven by hydrogen peroxide. Adv Synth Catal 344:932-937
18. Cirino PC, Arnold FH (2003) A self-sufficient peroxide-driven hydroxylation biocatalyst. Angew Chem Int Ed Engl 42(28):3299-3301
19. Coon MJ, Vaz AD, Bestervelt LL (1996) Cytochrome P450 2: peroxidative reactions of diversozymes. FASEB J 10(4):428-434
20. Cowart LA, Falck JR, Capdevila JH (2001) Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3. Arch Biochem Biophys 387(1):117-124
21. Cupp-Vickery JR, Poulos TL (1995) Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Nat Struct Biol 2(2):144-153
22. Dai R, Pincus MR, Friedman FK (1998) Molecular modeling of cytochrome P450 2B1: mode of membrane insertion and substrate specificity. J Protein Chem 17:121-129
23. Delcarte J, Fauconnier ML, Jacques P, Matsui K, Thonart P, Marlier M (2003) Optimisation of expression and immobilized metal ion affinity chromatographic purification of recombinant (His) (6)-tagged cytochrome P450 hydroperoxide lyase in Escherichia coli. J Chromatogr B Analyt Technol Biomed Life Sci 786:229-236
24. DeLuca JG, Dysart GR, Rasnick D, Bradley MO (1988) A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarin analog. Biochem Pharmacol 37(9):1731-1739
25. Dingler C, Ladner W, Krei G, Cooper B, Hauer B (1996) Preparation of (R)-2-(4-hydroxyphenoxypropionic acid by biotransformation. Pestic Sci 46:33-35
26. Duport C, Spagnoli R, Degryse E, Pompon D (1998) Self-sufficient biosynthesis of pregnenolone and progesterone in engineered yeast. Nat Biotechnol 16(2):186-189
27. England PA, Harford-Cross CF, Stevenson JA, Rouch DA, Wong LL (1998) The oxidation of naphthalene and pyrene by cytochrome P450cam. FEBS Lett 424(3):271-274
28. Estabrook RW, Shet MS, Faulkner KM, Fisher CW (1996a) The use of electrochemistry for the synthesis of 17 alpha-hydroxyprogesterone by a fusion protein containing P450c17. Endocr Res 22:665-671
29. Estabrook RW, Shet MS, Fisher CW, Jenkins CM, Waterman MR (1996b) The interaction of NADPH-P450 reductase with P450: an electrochemical study of the role of the flavin mononucleotide-binding domain. Arch Biochem Biophys 333:308-315
30. Estabrook RW, Faulkner KM, Shet MS, Fisher CW (1996c) Applications of electrochemistry for P450-catalyzed reactions. Methods Enzymol 272:44-51
31. Fang X, Halpert RJ (1996) Dithionite-supported hydroxylation of palmitic acid by cytochrome P450 BM-3. Drug Metab Dispos 24:1282-1285.
32. Farinas ET, Schwaneberg U, Glieder A, Arnold FH (2001) Directed evolution of a cytochrome P450 monooxygenase for alkane oxidation. Adv Synth Catal 343:601-606
33. Fernandez-Salguero P, Gutierrez-Merino C, Bunch AW (1993) Effect of immobilization on the activity of rat hepatic microsomal cytochrome P450 enzymes. Enzyme Microb Technol 15(2):100-104
34. Gilardi G, Meharenna YT, Tsotsou GE, Sadeghi SJ, Fairhead M, Giannini S (2002) Molecular Lego: design of molecular assemblies of P450 enzymes for nanobiotechnology. Biosens Bioelectron 17(1-2):133-145
35. Gill I (2001) Bio-doped nanocomposite polymers: sol-gel bioencapsulates. Chem Mater 13:3404-3421
36. Glieder A, Farinas ET, Arnold FH (2002) Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase. Nat Biotechnol 20(11):1135-1139
37. Graham SE, Peterson JA (1999) How similar are P450s and what can their differences teach us. Arch Biophys Biochem 369:24-29
38. Graham-Lorence S, Truan G, Peterson JA, Falck JR, Wei S, Helvig C, Capdevila JH (1997) An active site substitution, F87 V, converts cytochrome P450 BM-3 into a regio- and stereoselective (14S,15R)-arachidonic acid epoxygenase. J Biol Chem 272(2):1127-1135
39. Harford-Cross CF, Carmichael AB, Allan FK, England PA, Rouch DA, Wong L-L (2000) Protein engineering of cytochrome P450cam (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Prot Eng 13(2):121-128
40. Hasemann CA, Ravichandran KG, Peterson JA, Deisenhofer J (1994) Crystal structure and refinement of cytochrome P450terp at 2.3 A resolution. J Mol Biol 236(4):1169-1185
41. Hata M, Hirano Y, Hoshino T, Tsuda M (2001) Monooxygenation mechanism by cytochrome p-450. J Am Chem Soc 123(26):6410-6416
42. 2O)]2+: a versatile tool for efficient and non-enzymatic regeneration of nicotinamide and flavin coenzymes. J Mol Cat B Enzym 791:1-10
43. Hummel W, Kula M-R (1989) Dehydrogenases for the synthesis of chiral compounds. Eur J Biochem 184:1-13
44. Joo H, Lin Z, Arnold FH (1999) Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature 399:670-673
45. Kazlauskaite J, Westlake ACG, Wong L-L, Hill HAO (1996) Direct electrochemistry of of cytochrome P450cam. Chem Commun 18:2189-2190
46. King DL, Azari MR, Wiseman A (1988) Immobilization of cytochrome P-450 enzyme from Saccharomyces cerevisiae. Methods Enzymol 137:675-686
47. Kitazume T, Takaya N, Nakayama N, Shoun H (2000) Fusarium oxysporum fatty-acid subterminal hydroxylase (CYP505) is a membrane-bound eukaryotic counterpart of Bacillus megaterium cytochrome P450BM3. J Biol Chem 275(50):39734-39740
48. Klotz AV, Stegeman JJ, Walsh C (1984) An alternative 7-ethoxyresorufin O-deethylase activity assay: a continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity. Anal Biochem 140(1):138-145
49. Koebe HG, Pahemik S, Eyer P, Schildberg FW (1994a) Collagen gel immobilization: a useful cell culture technique for long-term metabolic studies on human hepatocytes. Xenobiotica 24(2):95-107
50. Koebe HG, Wick M, Cramer U, Lange V, Schildberg FW (1994b) Collagen gel immobilisation provides a suitable cell matrix for long term human hepatocyte cultures in hybrid reactors. Int J Artif Organs 17(2):95-106
51. Ladner W, Staudenmaier HR, Hauer B, Müller U, Pressler U, Meyer J, Siegel H (1999). Process for the hydroxylation of aromatic acids using strains of the fungus Beauveria. US Patent, 5,928,912, 27 July 1999
52. Lee TR, Hsu HP, Shaw GC (2001) Transcriptional regulation of the Bacillus subtilis bscR-CYP102A3 operon by the BscR repressor and differential induction of cytochrome CYP102A3 expression by oleic acid and palmitate. J Biochem (Tokyo) 130(4):569-574
53. Lei C, Wollenberger U, Jung C, Scheller FW (2000) Clay-bridged electron transfer between cytochrome p450(cam) and electrode. Biochem Biophys Res Commun 268(3):740-744
54. Lentz O, Li Q-S, Schwaneberg U, Lutz-Wahl S, Fischer P, Schmid RD (2001) Modification of the fatty acid specificity of cytochrome P450BM-3 from Bacillus megaterium by directed evolution: a validated assay. J Mol Cat B Enzym 15:123-133
55. Li H, Poulos TL (1997) The structure of the cytochrome p450BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nat Struct Biol 4(2):140-146
56. Li H, Poulos TL (1999) Fatty acid metabolism, conformational change, and electron transfer in cytochrome P-450(BM-3). Biochim Biophys Acta 1441(2-3):141-149
57. Li QS, Ogawa J, Schmid RD, Shimizu S (2001a) Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons. Appl Environ Microbiol 67(12):5735-5739
58. Li QS, Ogawa J, Schmid RD, Shimizu S (2001b) Residue size at position 87 of cytochrome P450 BM-3 determines its stereoselectivity in propylbenzene and 3-chlorostyrene oxidation. FEBS Lett 508(2):249-252
59. Maurer SC, Schulze H, Schmid RD, Urlacher V (2003) Immobilisation of P450BM-3 and an NADP(+) cofactor recycling system: Towards a technical application of heme-containing monooxygenases in fine chemical synthesis. Adv Synth Catal 345:802-810
60. McLean KJ, Cheesman MR, Rivers SL, Richmond A, Leys D, Chapman SK, Reid GA, Price NC, Kelly SM, Clarkson J, Smith WE, Munro AW (2002) Expression, purification and spectroscopic characterization of the cytochrome P450 CYP121 from Mycobacterium tuberculosis. J Inorg Biochem 91(4):527-541
61. Miles JS, Munro AW, Rospendowski BN, Smith WE, McKnight J, Thomson AJ (1992) Domains of the catalytically self-sufficient cytochrome P-450 BM-3. Genetic construction, overexpression, purification and spectroscopic characterization. Biochem J 288 (2):503-509
62. Miura Y, Fulco AJ (1975) Omega-1, omega-2 and omega-3 hydroxylation of long-chain fatty acids, amides and alcohols by a soluble enzyme system from Bacillus megaterium. Biochim Biophys Acta 388(3):305-317
63. Munro AW, Daff S, Coggins JR, Lindsay JG, Chapman SK (1996) Probing electron transfer in flavocytochrome P-450 BM3 and its component domains. Eur J Biochem 239(2):403-409
64. Nakahara K, Shoun H, Adachi S, Iizuka T, Shiro Y (1994) Crystallization and preliminary X-ray diffraction studies of nitric oxide reductase cytochrome P450nor from Fusarium oxysporum. J Mol Biol 239(1):158-159
65. Naqui A, Chance B, Cadenas E (1986) Reactive oxygen intermediates in biochemistry. Ann Rev Biochem 55:137-166
66. Nickerson DP, Harford-Cross CF, Fulcher SR, Wong LL (1997) The catalytic activity of cytochrome P450cam towards styrene oxidation is increased by site-specific mutagenesis. FEBS Lett 405(2):153-156
67. Oliver CF, Modi S, Sutcliffe MJ, Primrose WU, Lian LY, Roberts GC (1997) A single mutation in cytochrome P450 BM3 changes substrate orientation in a catalytic intermediate and the regiospecificity of hydroxylation. Biochemistry 36(7):1567-1572
68. Oster T, Boddupalli SS, Peterson JA (1991) Expression, purification, and properties of the flavoprotein domain of cytochrome P-450BM-3. Evidence for the importance of the amino-terminal region for FMN binding. J Biol Chem 266(33):22718-22725
69. Park SY, Yamane K, Adachi S, Shiro Y, Weiss KE, Sligar SG (2000) Crystallization and preliminary X-ray diffraction analysis of a cytochrome P450 (CYP119) from Sulfolobus solfataricus. Acta Crystallogr D Biol Crystallogr 56(9):1173-1175
70. Peters MW, Meinhold P, Glieder A, Arnold FH (2003) Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3. J Am Chem Soc 125(44):13442-13450
71. Peterson JA, Graham SE (1998) A close family resemblance: the importance of structure in understanding cytochromes P450. Structure 6(9):1079-1085
72. Petzoldt K, Annen K, Laurent H, Wiechert R (1982). Process for the preparation of 11-beta-hydroxy steroids. US Patent, 4,353,985, 12 October 1982
73. Picataggio S, Rohrer T, Deanda K, Lanning D, Reynolds R, Mielenz J, Eirich LD (1992) Metabolic engineering of Candida tropicalis for the production of long-chain dicarboxylic acids. Biotechnology (N Y) 10(8):894-898
74. Podust LM, Poulos TL, Waterman MR (2001) Crystal structure of cytochrome P450 14alpha -sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Proc Natl Acad Sci U S A 98(6):3068-3073
75. Podust LM, Kim Y, Arase M, Neely BA, Beck BJ, Bach H, Sherman DH, Lamb DC, Kelly SL, Waterman MR (2003) The 1.92-A structure of Streptomyces coelicolor A3(2) CYP154C1. A new monooxygenase that functionalizes macrolide ring systems. J Biol Chem 278(14):12214-12221
76. Poulos TL, Finzel BC, Howard AJ (1986) Crystal structure of substrate-free Pseudomonas putida cytochrome P-450. Biochemistry 25(18):5314-5322
77. Reipa V, Mayhew MP, Vilker VL (1997) A direct electrode-driven P450 cycle for biocatalysis. Proc Natl Acad Sci U S A 94(25):13554-13558
78. Rock D, Jones JP (2001) Inexpensive purification of P450 reductase and other proteins using 2′,5′-adenosine diphosphate agarose affinity columns. Protein Expr Purif 22(1):82-83
79. Schlichting I, Berendzen J, Chu K, Stock AM, Maves SA, Benson DE, Sweet RM, Ringe D, Petsko GA, Sligar SG (2000) The catalytic pathway of cytochrome p450cam at atomic resolution. Science 287(5458):1615-1622
80. Schwaneberg U, Sprauer A, Schmidt-Dannert C, Schmid RD (1999a) P450 monooxygenase in biotechnology. I. Single-step, large-scale purification method for cytochrome P450 BM-3 by anion-exchange chromatography. J Chromatogr A 848(1-2):149-159
81. Schwaneberg U, Schmidt-Dannert C, Schmitt J, Schmid RD (1999b) A continuous spectrophotometric assay for P450 BM-3, a fatty acid hydroxylating enzyme, and its mutant F87A. Anal Biochem 269(2):359-366
82. Schwaneberg U, Appel D, Schmitt J, Schmid RD (2000) P450 in biotechnology: zinc driven omega-hydroxylation of p-nitrophenoxydodecanoic acid using P450 BM-3 F87A as a catalyst. J Biotechnol 84(3):249-257
83. Schwaneberg U, Otey C, Cirino PC, Farinas E, Arnold FH (2001) Cost-effective whole-cell assay for laboratory evolution of hydroxylases in Escherichia coli. J Biomol Screen 6(2):111-117
84. Seelbach K, Riebel B, Hummel W, Kula M-R, Tishkov VI, Egorov AM, Wandrey C, Kragl U (1996) A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Lett 37(9):1377-1380
85. Sone T, Isobe M, Takabatake E, Ozawa N, Watabe T (1989) 7-ethenyloxycoumarin as a new substrate for fluorophotometric assay of hepatic microsomal epoxidizing activities. J Pharmacobiodyn 12(3):149-158
86. Stevenson J-A, Westlake ACG, Whittock C, Wong L-L (1996) The catalytic oxidation of linear and branched alkanes by cytochrome P450cam. J Am Chem Soc 118:12846-12847
87. Taylor M, Lamb DC, Cannell RJ, Dawson MJ, Kelly SL (2000) Cofactor recycling with immobilized heterologous cytochrome P450 105D1 (CYP105D1). Biochem Biophys Res Commun 279(2):708-711
88. Tischer W, Wedekind F (1999) Immobilized enzymes: methods and applications. Top Curr Chem 200:95-126
89. Tishkov VI, Galkin AG, Fedorchuk VV, Savitsky PA, Rojkova AM, Gieren H, Kula MR (1999) Pilot scale production and isolation of recombinant NAD+- and NADP+-specific formate dehydrogenases. Biotechnol Bioeng 64:187-193
90. Tsotsou GE, Cass AE, Gilardi G (2002) High throughput assay for cytochrome P450 BM3 for screening libraries of substrates and combinatorial mutants. Biosens Bioelectron 17(1-2):119-131
91. Urlacher V, Schmid RD (2002) Biotransformations using prokaryotic P450 monooxygenases. Curr Opin Biotechnol 13(6):557-564
92. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE (2000a) Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol Cell 5(1):121-131
93. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE (2000b) Microsomal cytochrome P450 2C5: comparison to microbial P450s and unique features. J Inorg Biochem 81(3):183-190
94. Williams PA, Cosme J, Ward A, Angove HC, Matak Vinkovic D, Jhoti H (2003) Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature 424:464-468
95. Woyski D, Cupp-Vickery JR (2001) Enhanced expression of cytochrome P450s from lac-based plasmids using lactose as the inducer. Arch Biochem Biophys 388(2):276-280
96. Yano JK, Blasco F, Li H, Schmid RD, Henne A, Poulos TL (2003) Preliminary characterization and crystal structure of a thermostable cytochrome P450 from Thermus thermophilus. J Biol Chem 278(1):608-616
97. Zhang Z, Chouchane S, Magliozzo RS, Rusling JF (2002) Direct voltammetry and catalysis with Mycobacterium tuberculosis catalase-peroxidase, peroxidases, and catalase in lipid films. Anal Chem 74(1):163-170