Molecular evolution of a steroid hydroxylating cytochrome P450 using a versatile steroid detection system for screening

Lipids

Volumn 43, Issue 12, 2008, Pages 1133-1141

  Virus, Cornelia ^a   Bernhardt, Rita ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Bacterial cytochrome P450; Biotransformation; CYP106A2; Directed evolution; Steroid; Whole cell biocatalysis

Indexed keywords

ADRENODOXIN; CORTODOXONE; CYTOCHROME P450; CYTOCHROME P450 CYP106A2; PROGESTERONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ENZYME MECHANISM; ENZYME STRUCTURE; HYDROXYLATION; MOLECULAR EVOLUTION; MUTAGENESIS; MUTATION; NONHUMAN; SCREENING;

ADRENODOXIN; BACILLUS MEGATERIUM; BACTERIAL PROTEINS; BIOLOGICAL ASSAY; CORTODOXONE; CYTOCHROME P-450 ENZYME SYSTEM; DIRECTED MOLECULAR EVOLUTION; FERREDOXIN-NADP REDUCTASE; MODELS, MOLECULAR; MUTAGENESIS; PROTEIN STRUCTURE, TERTIARY; STEROIDS;

BACILLUS MEGATERIUM; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 57149131662     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-008-3236-8     Document Type: Article

References (41)

1. R Bernhardt 2006 Cytochromes P450 as versatile biocatalysts J Biotechnol 124 128 145
2. EM Isin FP Guengerich 2007 Complex reactions catalyzed by cytochrome P450 enzymes Biochim Biophys Acta 1770 314 329
3. F Hannemann A Bichet KM Ewen R Bernhardt 2007 Cytochrome P450 systems-biological variations of electron transport chains Biochim Biophys Acta 1770 330 344
4. P Fernandes A Cruz B Angelova HM Pinheiro JMS Cabral 2003 Microbial conversion of steroid compounds: recent developments Enzyme Microb Technol 32 688 705
5. A Chefson K Auclair 2006 Progress towards the easier use of P450 enzymes Mol Biosyst 2 462 469
6. SB Mahato S Garai 1997 Advances in microbial steroid biotransformation Steroids 62 332 345
7. A Jekkel É Ilkóy G Horváth I Pallagi J Süto G Ambrus 1998 Microbial hydroxylation of 13β-ethyl-4-gonene-3, 17-dione J Mol Catal B Enzym 5 385 387
8. MC Orencia JS Yoon JE Ness WP Stemmer RC Stevens 2001 Predicting the emergence of antibiotic resistance by directed evolution and structural analysis Nat Struct Biol 8 238 242
9. DJ Hart F Tarendeau 2006 Combinatorial library approaches for improving soluble protein expression in Escherichia coli Acta Crystallogr D Biol Crystallogr 62 19 26
10. D Appel RD Schmid CA Dragan M Bureik VB Urlacher 2005 A fluorimetric assay for cortisol Anal Bioanal Chem 383 182 186
11. F Hannemann C Virus R Bernhardt 2006 Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases J. Biotechnol 124 172 181
12. A Berg JA Gustafsson M Ingelman-Sundberg 1976 Characterization of a cytochrome P-450-dependent steroid hydroxylase system present in Bacillus megaterium J Biol Chem 251 2831 2838
13. M Lisurek MJ Kang RW Hartmann R Bernhardt 2004 Identification of monohydroxy progesterones produced by CYP106A2 using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry Biochem Biophys Res Commun 319 677 682
14. C Virus M Lisurek B Simgen F Hannemann R Bernhardt 2006 Function and engineering of the 15beta-hydroxylase CYP106A2 Biochem Soc Trans 34 1215 1218
15. A Berg M Ingelman-Sundberg JA Gustafsson 1979 Purification and characterization of cytochrome P-450meg J Biol Chem 254 5264 5271
16. B Simgen J Contzen R Schwarzer R Bernhardt C Jung 2000 Substrate binding to 15beta-hydroxylase (CYP106A2) probed by FT infrared spectroscopic studies of the iron ligand CO stretch vibration Biochem Biophys Res Commun 269 737 742
17. Y Sagara A Wada Y Takata MR Waterman K Sekimizu T Horiuchi 1993 Direct expression of adrenodoxin reductase in Escherichia coli and the functional characterization Biol Pharm Bull 16 627 630
18. H Uhlmann V Beckert D Schwarz R Bernhardt 1992 Expression of bovine adrenodoxin in E. coli and site-directed mutagenesis of/2 Fe-2S/cluster ligands Biochem Biophys Res Commun 188 1131 1138
19. M Lisurek B Simgen I Antes R Bernhardt 2008 Theoretical and experimental evaluation of a CYP106A2 low homology model and production of mutants with changed activity and selectivity of hydroxylation Chembiochem 9 1439 1449
20. N Guex MC Peitsch 1997 SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18 2714 2723
21. P Volin 1995 High-performance liquid chromatographic analysis of corticosteroids J Chromatogr B 671 319 340
22. K Shimada K Mitamura T Higashi 2001 Gas chromatography and high-performance liquid chromatography of natural steroids J Chromatogr A 935 141 172
23. JG Lewis L Manley JC Whitlow PA Elder 1992 Production of a monoclonal antibody to cortisol: application to a direct enzyme-linked immunosorbent assay of plasma Steroids 57 82 85
24. M Mirasoli SK Deo JC Lewis A Roda S Daunert 2002 Bioluminescence immunoassay for cortisol using recombinant aequorin as a label Anal Biochem 306 204 211
25. JW Goldzieher JM Bodenchuk P Nolan 1954 Fluorescence reactions of steroids Anal Chem 26 853 856
26. AR Dunn IJ Dmochowski AM Bilwes HB Gray BR Crane 2001 Probing the open state of cytochrome P450cam with ruthenium-linker substrates Proc Natl Acad Sci USA 98 12420 12425
27. SY Park K Yamane S Adachi Y Shiro KE Weiss SA Maves SG Sligar 2002 Thermophilic cytochrome P450 (CYP119) from Sulfolobus solfataricus: high resolution structure and functional properties J Inorg Biochem 91 491 501
28. LM Geren P O'Brien J Stonehuerner F Millett 1984 Identification of specific carboxylate groups on adrenodoxin that are involved in the interaction with adrenodoxin reductase J Biol Chem 259 2155 2160
29. L Geren J Tuls P O'Brien F Millett JA Peterson 1986 The involvement of carboxylate groups of putidaredoxin in the reaction with putidaredoxin reductase J Biol Chem 261 15491 15495
30. R Bernhardt A Makower G-R Jänig K Ruckpaul 1984 Selective chemical modification of a functionally linked lysine in cytochrome P-450LM2 Biochim Biophys Acta 785 186 190
31. R Bernhardt K Pommerening K Ruckpaul 1987 Modification of carboxyl groups on NADPH-cytochrome P-450 reductase involved in binding of cytochromes c and P-450LM2 Biochem Int 14 823 832
32. VM Coghlan LE Vickery 1991 Site-specific mutations in human ferredoxin that affect binding to ferredoxin reductase and cytochrome P450scc J Biol Chem 266 18606 18612
33. PS Stayton SG Sligar 1990 The cytochrome P-450cam binding surface as defined by site-directed mutagenesis and electrostatic modeling Biochemistry 29 7381 7386
34. A Wada MR Waterman 1992 Identification by site-directed mutagenesis of two lysine residues in cholesterol side chain cleavage cytochrome P450 that are essential for adrenodoxin binding J Biol Chem 267 22877 22882
35. TC Pochapsky TA Lyons S Kazanis T Arakaki G Ratnaswamy 1996 A structure-based model for cytochrome P450cam-putidaredoxin interactions Biochimie 78 723 733
36. H Koga Y Sagara T Yaoi M Tsujimura K Nakamura K Sekimizu R Makino H Shimada Y Ishimura K Yura 1993 Essential role of the Arg112 residue of cytochrome P450cam for electron transfer from reduced putidaredoxin FEBS Lett 331 109 113
37. K Nakamura T Horiuchi T Yasukochi K Sekimizu T Hara Y Sagara 1994 Significant contribution of arginine-112 and its positive charge of Pseudomonas putida cytochrome P-450cam in the electron transport from putidaredoxin Biochim Biophys Acta 20 40 48
38. M Unno H Shimada Y Toba R Makino Y Ishimura 1996 Role of Arg112 of cytochrome p450cam in the electron transfer from reduced putidaredoxin. Analyses with site-directed mutants J Biol Chem 271 17869 17874
39. A Roitberg M Holden M Mayhew IV Kurnikov DN Beratan V Vilker 1998 Binding and electron transfer between putidaredoxin and cytochrome P450cam. Theory and experiments J Am Chem Soc 120 8927 8932
40. PS Stayton TL Poulos SG Sligar 1989 Putidaredoxin competitively inhibits cytochrome b5-cytochrome P-450cam association: a proposed molecular model for a cytochrome P-450cam electron-transfer complex Biochemistry 28 8201 8205
41. A Bichet F Hannemann M Rekowski R Bernhardt 2007 A new application of the yeast two-hybrid system in protein engineering Protein Eng Des Sel 20 117 123