Sequence analysis and heterologous expression of a new cytochrome P450 monooxygenase from Rhodococcus sp. for asymmetric sulfoxidation

Applied Microbiology and Biotechnology

Volumn 85, Issue 3, 2010, Pages 615-624

  Zhang, Jian Dong ^a   Li, Ai Tao ^a   Yang, Yi ^a   Xu, Jian He ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric sulfoxidation; Cloning; Cytochrome P450 monooxygenase; Expression; Rhodococcus sp

Indexed keywords

ASYMMETRIC SULFOXIDATION; CYTOCHROME P450; MONOOXYGENASES; RHODOCOCCUS SP; SULFOXIDATION;

AMIDES; AMINO ACIDS; CLONING; ENZYMES; ESCHERICHIA COLI; ORGANIC ACIDS; PURIFICATION; SYNTHESIS (CHEMICAL);

ENZYME ACTIVITY;

AMINO ACID; ANISOLE DERIVATIVE; CYTOCHROME P450 OXYGENASE; DNA FRAGMENT; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

AMINO ACID; BACTERIUM; CATALYST; CYTOCHROME; DNA; ENZYME ACTIVITY; GENE EXPRESSION; MICROBIAL ACTIVITY; OXIDATION; PROTEIN; SULFIDE;

ARTICLE; BACTERIAL GENE; BIOCATALYST; BIOTRANSFORMATION; CONTROLLED STUDY; DNA SEQUENCE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME PURIFICATION; ESCHERICHIA COLI; GENE EXPRESSION; MOLECULAR CLONING; NONHUMAN; OXIDATION; PH; PROTEIN EXPRESSION; RHODOCOCCUS; SEQUENCE ANALYSIS; STEREOCHEMISTRY; SULFOXIDATION;

BACTERIAL PROTEINS; CLONING, MOLECULAR; COENZYMES; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME STABILITY; ESCHERICHIA COLI; GENE EXPRESSION; HYDROGEN-ION CONCENTRATION; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; NADP; OXIDATION-REDUCTION; RHODOCOCCUS; SEQUENCE ANALYSIS, DNA; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFIDES; SULFOXIDES; TEMPERATURE;

ESCHERICHIA COLI; RHODOCOCCUS; RHODOCOCCUS SP.; RHODOCOCCUS SP. NCIMB 9784;

EID: 74149089418     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2118-1     Document Type: Article

References (41)

1. KS Bell JC Philp DW Aw N Christofi 1998 The genus Rhodococcus J Appl Microbiol 85 195 210 10.1046/j.1365-2672.1998.00525.x 1:CAS:528: DyaK1cXmtFWkt7s%3D (Pubitemid 28396796)
2. S Chauvaux F Chevalier C Le Dantec F Fayolle I Miras F Kunst P Beguin 2001 Cloning of a genetically unstable cytochrome P-450 gene cluster involved in degradation of the pollutant ethyl tert-butyl ether by Rhodococcus ruber J Bacteriol 183 6551 6557 10.1128/JB.183.22.6551-6557.2001 1:CAS:528: DC%2BD3MXotFWnu7o%3D (Pubitemid 33026745)
3. U Dehmel KH Engesser KN Timmis DF Dwyer 1995 Cloning, nucleotide sequence, and expression of the gene encoding a novel dioxygenase involved in metabolism of carboxydiphenyl ethers in Pseudomonas pseudoalcaligenes POB310 Arch Microbiol 163 35 41 10.1007/BF00262201 1:CAS:528:DyaK2MXkvVOhsL8%3D
4. DR Boyd ND Sharma SA Haughey MA Kennedy BT McMurray GN Sheldrake CCR Allen H Dalton K Sproule 1998 Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides J Chem Soc, Perkin Trans 1 12 1929 1934 10.1039/a801515e
5. J Fruetel YT Chang J Collins G Loew PR Ortiz de Montellano 1994 Thioanisole sulfoxidation by cytochrome P450cam (CYP101): experimental and calculated absolute stereochemistries J Am Chem Soc 116 11643 11648 10.1021/ja00105a003 1:CAS:528:DyaK2MXitlWgu7s%3D
6. Y Furusawa V Nagarajan M Tanokura E Masai M Fukuda T Senda 2004 Crystal structure of the terminal oxygenase component of biphenyl dioxygenase derived from Rhodococcus sp. strain RHA1 J Mol Biol 342 1041 1052 10.1016/j.jmb.2004.07. 062 1:CAS:528:DC%2BD2cXntlOgsLc%3D (Pubitemid 39165666)
7. H Guo J Xiong 2006 A specific and versatile genome walking technique Gene 381 18 23 10.1016/j.gene.2006.06.002 1:CAS:528:DC%2BD28XhtVWks7nN (Pubitemid 44436764)
8. MABD Hamman SA Haehner-Daniels AE Wrighton SD Rettie Hall 2000 Stereoselective sulfoxidation of sulindac sulfide by flavin-containing monooxygenases. Comparison of human liver and kidney microsomes and mammalian enzymes Biochem Pharmacol 60 7 17 10.1016/S0006-2952(00)00301-4 1:CAS:528:DC%2BD3cXjtVCitr0%3D (Pubitemid 30243080)
9. D Harshavardhan C Ranajit SY Jagjit 2005 Genome-wide structural and evolutionary analysis of the P450 monooxygenase genes (P450ome) in the white rot fungus Phanerochaete chrysosporium: evidence for gene duplications and extensive gene clustering BMC Genomics 6 92 10.1186/1471-2164-6-92 (Pubitemid 41372183)
10. HL Holland 1988 Chiral sulfoxidation by biotransformation of organic sulfides Chem Rev 88 473 485 10.1021/cr00085a002 1:CAS:528:DyaL1cXhvVaqtrw%3D
11. Holland HL (1992) Organic synthesis with oxidative enzymes. VCH, New York, p 255
12. HL Holland 2001 Biotransformation of organic sulfides Nat Prod Rep 18 171 181 10.1039/b002681f 1:CAS:528:DC%2BD3MXitFylsLg%3D (Pubitemid 32324688)
13. HL Holland FM Brown A Kerridge P Penkos J Arensdor 2003 Biotransformation of sulfides by Rhodococcus erythropolis J Mol Catal B: Enzymatic 22 219 223 10.1016/S1381-1177(03)00040-7 1:CAS:528:DC%2BD3sXjvFagtL8%3D (Pubitemid 36578987)
14. F Inmaculada K Noureddine 2003 Recent developments in the synthesis and utilization of chiral sulfoxides Chem Rev 103 3651 3705 10.1021/cr990372u
15. RG Jackson EL Rylott D Fournier J Hawari NC Bruce 2007 Exploring the biochemical properties and remediation applications of the unusual explosive-degrading P450 system XplA/B Proc Natl Acad Sci USA 104 16822 16826 10.1073/pnas.0705110104 1:CAS:528:DC%2BD2sXht1KgtLvJ (Pubitemid 350210949)
16. U Karlson DF Dwyer SW Hooper ER Moore KN Timmis LD Eltis 1993 Two independently regulated cytochromes P-450 in a Rhodococcus rhodochrous strain that degrades 2-ethoxyphenol and 4-methoxybenzoate J Bacteriol 175 1467 1474 1:CAS:528:DyaK3sXktVCltLk%3D
17. JD Lambeth DW Seybert JR Lancaster JC Salerno H Kamin 1982 Steroidogenic electron transport in adrenal cortex mitochondria Mol Cell Biochem 45 13 31 10.1007/BF01283159 1:CAS:528:DyaL38Xks1Oru7o%3D (Pubitemid 13227611)
18. MJ Larkin R De Mot LA Kulakov I Nagy 1998 Applied aspects of Rhodococcus genetics Antonie Van Leeuwenhoek 74 133 153 10.1023/A:1001776500413 1:CAS:528:DyaK1MXhvVSht7Y%3D (Pubitemid 29078193)
19. MJ Larkin LA Kulakov CCR Allen 2005 Biodegradation and Rhodococcus-masters of catabolic versatility Curr Opin Biotechnol 16 282 290 10.1016/j.copbio.2005.04.007 1:CAS:528:DC%2BD2MXlt1Wis74%3D (Pubitemid 40806465)
20. AT Li JD Zhang JH Xu WY Lu GQ Lin 2009 Isolation of Rhodococcus sp. ECU0066: a new sulfide monooxygenase producing strain for asymmetric sulfoxidation Appl Environ Microbiol 75 551 556 10.1128/AEM.01527-08 1:CAS:528:DC%2BD1MXktlejtrc%3D
21. L Liu RD Schmid VB Urlacher 2006 Cloning, expression, and characterization of a self-sufficient cytochrome P450 monooxygenase from Rhodococcus ruber DSM 44319 Appl Microbiol Biotechnol 72 876 882 10.1007/s00253-006-0355-0 1:CAS:528:DC%2BD28XhtVWhsrvK (Pubitemid 44477363)
22. ZA Malik CC Allen L Gakhar DA Lipscomb MJ Larkin S Ramaswamy 2002 Crystallization and preliminary X-ray diffraction analysis of naphthalene dioxygenase from Rhodococcus sp. strain NCIMB 12038 Acta Crystallogr D Biol Crystallogr 58 2173 2174 10.1107/S0907444902016803 (Pubitemid 35450854)
23. EG Mata 1996 Recent advances in the synthesis of sulfoxides from sulfides Phosphorus 117 231 286 10.1080/10426509608038790 1:CAS:528:DyaK2sXjs1Cjs7w%3D
24. M Maurice L Pichard M Daujat I Fabre H Joyeux J Domergue P Maurel 1992 Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture FASEB J 6 752 758 1:CAS:528:DyaK38Xhs1Grs74%3D
25. MP McLeod RL Warren WWL Hsiao N Araki M Myhre C Fernandes D Miyazawa W Wong AL Lillquist D Wang M Dosanjh H Hara A Petrescu RD Morin G Yang JM Stott JE Schein H Shin D Smailus AS Siddiqui MA Marra SJM Jones R Holt FSL Brinkman K Miyauchi M Fukuda JE Davies WW Mohn LD Eltis 2006 The complete genome of Rhodococcus sp. RHA1 provides insights into a catabolic powerhouse Proc Natl Acad Sci U S A 103 15582 15587 10.1073/pnas.0607048103 (Pubitemid 44625635)
26. Mikolajczyk M, Drabowicz J, Kielbasinski P (1997) Chiral sulfur reagents: applications in asymmetric and stereoselective synthesis. CRC, Boca Raton
27. AW Munro JG Lindsay JR Coggins SM Kelly NC Price 1996 Analysis of the structural stability of the multidomain enzyme flavocytochrome P-450 BM3 Biochim Biophys Acta 1296 127 137
28. I Nagy G Schoofs F Compernolle P Proost J Vanderleyden R de Mot 1995 Degradation of the thiocarbamate herbicide EPTC (S-ethyl dipropylcarbamothioate) and biosafening by Rhodococcus sp. strain NI86/21 involve an inducible cytochrome P-450 system and aldehyde dehydrogenase J Bacteriol 177 676 687 1:CAS:528:DyaK2MXjtlegsrg%3D
29. N Nakayama A Takemae H Shoun 1996 Cytochrome P450foxy, a catalytically self-sufficient fatty acid hydroxylase of the fungus Fusarium oxysporum J Biochem (Tokyo) 119 435 440 1:CAS:528:DyaK28Xjt1agtL8%3D
30. MK Nanne JJO Arjen WF Marco BJ Dick 2003 Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase Appl Environ Microbiol 69 419 426 10.1128/AEM.69.1.419-426.2003 (Pubitemid 36077503)
31. T Omura R Sato 1964 The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J Biol Chem 239 2370 2378 1:CAS:528:DyaF2cXktF2gur4%3D
32. RC Prince MJ Grossman 2003 Substrate preferences in biodesulfurization of diesel range fuels by Rhodococcus sp. strain ECRD-1 Appl Environ Microbiol 69 5833 5838 10.1128/AEM.69.10.5833-5838.2003 1:CAS:528:DC%2BD3sXotlGqtbc%3D (Pubitemid 37280301)
33. GA Roberts G Grogan A Greter SL Flitsch NJ Turner 2002 Identification of a new class of cytochrome P450 from a Rhodococcus sp J Bacteriol 184 3898 3908 10.1128/JB.184.14.3898-3908.2002 1:CAS:528:DC%2BD38XltVyktLk%3D (Pubitemid 34705447)
34. GA Roberts A Celik DJ Hunter TW Ost JH White SK Chapman NJ Turner SL Flitsch 2003 A self-sufficient cytochrome P450 with a primary structural organization that includes a flavin domain and a [2Fe-2S] redox center J Biol Chem 278 48914 48920 10.1074/jbc.M309630200 1:CAS:528:DC%2BD3sXptlGku74%3D
35. Sambrook J, Russell DW (2001) Molecular cloning: a laboratory manual, 3rd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor
36. HM Seth-Smith SJ Rosser A Basran ER Travis ER Dabbs S Nicklin NC Bruce 2002 Cloning, sequencing, and characterization of the RDX hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine degradation gene cluster from Rhodococcus rhodochrous 11Y Appl Environ Microbiol 68 4764 4771 10.1128/AEM.68.10.4764-4771. 2002 1:CAS:528:DC%2BD38XnvFClt7g%3D (Pubitemid 35154779)
37. Y Tanaka T Matsui J Konishi K Maruhashi R Kurane 2002 Biodesulfurization of benzothiophene and dibenzothiophene by a newly isolated Rhodococcus strain Appl Microbiol Biotechnol 59 325 328 10.1007/s00253-002-0985-9 1:CAS:528:DC%2BD38XlvV2rsro%3D (Pubitemid 34756978)
38. A Verras A Alian PR Ortiz de Montellano 2006 Cytochrome P450 active site plasticity: attenuation of imidazole binding in cytochrome P450cam by an L244A mutation Protein Eng Design Selection 19 491 496 10.1093/protein/gzl035 1:CAS:528:DC%2BD28XhtFeisb%2FL (Pubitemid 44627321)
39. AM Warhurst CA Fewson 1994 Biotransformations catalyzed by the genus Rhodococcus Crit Rev Biotechnol 14 29 73 10.3109/07388559409079833 1:CAS:528:DyaK2cXlt12nsLs%3D
40. D Werck-Reichhart R Feyereisen 2000 Cytochromes P450: a success story Genome Biol 1 3003.1 3003.9 10.1186/gb-2000-1-6-reviews3003
41. WJ Zhang R Yamini 2002 Inhibition of cytochromes P450 by antifungal imidazole derivatives Drug Metab Disp 30 314 318 10.1124/dmd.30.3.314 1:CAS:528:DC%2BD38Xhtl2qt7k%3D (Pubitemid 34175023)