Characterization of diverse natural variants of CYP102A1 found within a species of bacillus megaterium

AMB Express

Volumn 1, Issue 1, 2011, Pages 1-12

  Kang, Ji Yeon ^a   Kim, So Young ^a   Kim, Dooil ^a   Kim, Dong Hyun ^a   Shin, Sun Mi ^a   Park, Sun Ha ^a   Kim, Keon Hee ^a   Jung, Heung Chae ^b   Pan, Jae Gu ^b   Joung, Young Hee ^a   Chi, Youn Tae ^a   Chae, Ho Zoon ^a   Ahn, Taeho ^a   Yun, Chul Ho ^a  

^a Chonnam National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 BM3; LAURIC ACID; MYRISTIC ACID; PALMITIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; BACILLUS MEGATERIUM; BACTERIAL STRAIN; BINDING AFFINITY; ENZYME ACTIVITY; GENE MUTATION; GENETIC VARIABILITY; HYDROXYLATION; MICROBIAL DIVERSITY; MUTATION RATE; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PHYLOGENY; POLYMERASE CHAIN REACTION; PROTEIN EXPRESSION; PROTEIN PURIFICATION; SEQUENCE ANALYSIS; THERMOSTABILITY;

EID: 84855959860     PISSN: None     EISSN: 21910855     Source Type: Journal    
DOI: 10.1186/2191-0855-1-1     Document Type: Article

References (46)

1. Aharoni A, Gaidukov L, Khersonsky O, McQGould S, Roodveldt C, Tawfik DS (2005) The 'evolvability' of promiscuous protein functions. Nat Genet 37:73-76.
2. Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215:403-410.
3. Atrakchi AH (2009) Interpretation and considerations on the safety evaluation of human drug metabolites. Chem Res Toxicol 22:1217-1220.
4. Bernhardt R (2006) Cytochromes P450 as versatile biocatalysts. J Biotechnol 124:128-145.
5. Boddupalli SS, Estabrook RW, Peterson JA (1990) Fatty acid monooxygenation by cytochrome P-450BM-3. J Biol Chem 265:4233-4239.
6. Eiben S, Bartelmas H, Urlacher VB (2007) Construction of a thermostable cytochrome P450 chimera derived from self-sufficient mesophilic parents. Appl Microbiol Biotechnol 75:1055-1061.
7. 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.
8. Girvan HM, Levy CW, Williams P, Fisher K, Cheesman MR, Rigby SE, Leys D, Munro AW (2010) Glutamate-haem ester bond formation is disfavoured in flavocytochrome P450. BM3: characterization of glutamate substitution mutants at the haem site of P450. BM3. Biochem J 427:455-466.
9. Guengerich FP (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 14:611-650.
10. Guengerich FP (2003) Cytochromes P450, drugs, and diseases. Mol Interv 3:194-204.
11. Guengerich FP (2005) Human Cytochrome P450. Enzymes. In: Ortiz de Montellano PR (ed) Cytochrome P450: Structure, Mechanism, and Biochemistry. Kluwer Academic/Plenum Publishers, New York pp 377-530.
12. Gürtler V (1999) The role of recombination and mutation in 16S-23S rDNA spacer rearrangements. Gene 238:241-252.
13. Gustafsson MC, Roitel O, Marshall KR, Noble MA, Chapman SK, Pessegueiro A, Fulco AJ, Cheesman MR, von Wachenfeldt C, Munro AW (2004) Expression, purification, and characterization of Bacillus subtilis cytochromes P450. CYP102A2 and CYP102A3: flavocytochrome homologues of P450. BM3 from Bacillus megaterium. Biochemistry 43:5474-5487.
14. Huang N, Agrawal V, Giacomini KM, Miller WL (2008) Genetics of P450 oxidoreductase: sequence variation in 842 individuals of four ethnicities and activities of 15 missense mutations. Proc Natl Acad Sci USA 105:1733-1738.
15. Johnson MD, Zuo H, Lee KH, Trebley JP, Rae JM, Weatherman RV, Desta Z, Flockhart DA, Skaar TC (2004) Pharmacological characterization of 4-hydroxy- N-desmethyl tamoxifen, a novel active metabolite of tamoxifen. Breast Cancer Res Treat 85:151-159.
16. Kelly SL, Kelly DE, Jackson CJ, Warrilow AG, Lamb DC (2005) The Diversity and Importance of Microbial Cytochrome P450. in: P.R. Ortiz de Montellano (ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry. Kluwer Academic/Plenum Publishers, New York pp 585-617.
17. Khersonsky O, Roodveldt C, Tawfik DS (2006) Enzyme promiscuity: evolutionary and mechanistic aspects. Curr Opin Biotechnol 10:498-508.
18. Kim DH, Ahn T, Jung HC, Pan JG, Yun CH (2009) Generation of the human metabolite piceatannol from the anticancer-preventive agent resveratrol by bacterial cytochrome P450. BM3. Drug Metab Dispos 37:932-936.
19. Kim DH, Kim KH, Isin EM, Guengerich FP, Chae HZ, Ahn T, Yun CH (2008a) Heterologous expression and characterization of wild-type human cytochrome P450 1A2 without conventional N-terminal modification in Escherichia coli. Protein Expr Purif 57:188-200.
20. Kim DH, Kim KH, Kim DH, Liu KH, Jung HC, Pan JG, Yun CH (2008b) Generation of human metabolites of 7-ethoxycoumarin by bacterial cytochrome P450. BM3. Drug Metab Dispos 36:2166-2170.
21. Kim DH, Kim KH, Kim D, Jung HC, Pan JG, Chi YT, Ahn T, Yun CH (2010) Oxidation of human cytochrome P450 1A2 substrates by Bacillus megaterium cytochrome P450. BM3. J Mol Catal B: Enzym 63:179-187.
22. Kim KH, Kang JY, Kim DH, Park SH, Park SH, Kim D, Park KD, Lee YJ, Jung HC, Pan JG, Ahn T, Yun CH (2011) Generation of human chiral metabolites of simvastatin and lovastatin by bacterial CYP102A1 mutants. Drug Metab Dispos 39:140-150.
23. Kitazume T, Haines DC, Estabrook RW, Chen B, Peterson JA (2007) Obligatory intermolecular electron-transfer from FAD to FMN in dimeric P450BM-3. Biochemistry 46:11892-11901.
24. Leclercq L, Cuyckens F, Mannens GS, de Vries R, Timmerman P, Evans DC (2009) Which human metabolites have we MIST? Retrospective analysis, practical aspects, and perspectives for metabolite identification and quantification in pharmaceutical development. Chem Res Toxicol 22:280-293.
25. Lentz O, Li QS, Schwaneberg U, Lutz-Wahl S, Fischer P, Schmid RD (2001) Modification of the fatty acid specificity of cytochrome P450. BM-3 from Bacillus megaterium by directed evolution: a validated assay. J Mol Catal B: Enzym 15:123-133.
26. Lewis DF, Watson E, Lake BG (1998) Evolution of the cytochrome P450 superfamily: sequence alignments and pharmacogenetics. Mutat Res 410:245-270.
27. 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 4:140-146.
28. Ni Y, Wan D, He K (2008) 16S rDNA and 16S-23S internal transcribed spacer sequence analyses reveal inter- and intraspecific Acidithiobacillus phylogeny. Microbiology 154:2397-2407.
29. Noble MA, Miles CS, Chapman SK, Lysek DA, MacKay AC, Reid GA, Hanzlik RP, Munro AW (1999) Roles of key active-site residues in flavocytochrome P450. BM3. Biochem J 339:371-379.
30. Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2379-2385.
31. Park SH, Kim DH, Kim D, Kim DH, Jung HC, Pan JG, Ahn T, Kim D, Yun CH (2010) Engineering bacterial cytochrome P450. BM3 into a prototype with human P450 enzyme activity using indigo formation. Drug Metab Dispos 38:732-739.
32. Peters MW, Meinhold P, Glieder A, Arnold FH (2003) Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450. BM-3. J Am Chem Soc 125:13442-13450.
33. Porwal S, Lal S, Cheema S, Kalia VC (2009) Phylogeny in aid of the present and novel microbial lineages: Diversity in Bacillus. PLoS One 4:e4438.
34. Ravichandran KG, Boddupalli SS, Hasermann CA, Peterson JA, Deisenhofer J (1993) Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's. Science 261:731-736.
35. Ruettinger RT, Wen LP, Fulco AJ (1989) Coding nucleotide, 5' regulatory, and deduced amino acid sequences of P-450BM-3, a single peptide cytochrome P-450:NADPH-P-450 reductase from Bacillus megaterium. J Biol Chem 264:10987-10995.
36. Sawayama AM, Chen MK, Kulanthaivel P, Kuo MS, Hemmerle H, Arnold FH (2009) A panel of cytochrome P450. BM3 variants to produce drug metabolites and diversify lead compounds. Chemistry 15:11723-11729.
37. Seifert A, Vomund S, Grohmann K, Kriening S, Urlacher VB, Laschat S, Pleiss J (2009) Rational design of a minimal and highly enriched CYP102A1 mutant library with improved regio-, stereo- and chemoselectivity. Chembiochem 10:853-861.
38. Stjernschantz E, van Vugt-Lussenburg BM, Bonifacio A, de Beer SB, van der Zwan G, Gooijer C, Commandeur JN, Vermeulen NP, Oostenbrink C (2008) Structural rationalization of novel drug metabolizing mutants of cytochrome P450. BM3. Proteins 71:336-352.
39. Thompson JD, Gibson TJ, Plewniak F, Jeanmougin F, Higgins DG (1997) The CLUSTAL_X windows interface: flexible strategies for multiple sequence alignment aided by quality analysis tools. Nucleic Acids Res 25:4876-4882
40. van Vugt-Lussenburg BM, Stjernschantz E, Lastdrager J, Oostenbrink C, Vermeulen NP, Commandeur JN (2007) Identification of critical residues in novel drug metabolizing mutants of cytochrome P450. BM3 using random mutagenesis. J Med Chem 50:455-461.
41. Whitehouse CJ, Bell SG, Tufton HG, Kenny RJ, Ogilvie LC, Wong LL (2008) Evolved CYP102A1 (P450BM3) variants oxidise a range of non-natural substrates and offer new selectivity options. Chem Commun (Camb) 28:966-968.
42. Whitehouse CJ, Bell SG, Yang W, Yorke JA, Blanford CF, Strong AJ, Morse EJ, Bartlam M, Rao Z, Wong LL (2009) A highly active single-mutation variant of P450BM3 (CYP102A1). Chembiochem 10:1654-1656.
43. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE (2004) Drug-drug interactions for UDPglucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201-1208.
44. Woese CR, Kandler O, Wheelis ML (1990) Towards a natural system of organisms: proposal for the domains Archaea, Bacteria, and Eucarya. Proc Natl Acad Sci USA 87:4576-4579.
45. Yun CH, Kim KH, Kim DH, Jung HC, Pan JG (2007) The bacterial P450. BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol 25:289-298.
46. Yun CH, Yim SK, Kim DH, Ahn T (2006) Functional expression of human cytochrome P450 enzymes in Escherichia coli. Curr Drug Metab 7:411-429