Benzene oxygenation and oxidation by the peroxygenase of Agrocybe aegerita

AMB Express

Volumn 3, Issue , 2013, Pages 1-8

  Karich, Alexander ^a   Kluge, Martin ^a   Ullrich, René ^a   Hofrichter, Martin ^a  

^a International Graduate School Zittau   (Germany)

Author keywords

Epoxide; Oxepin; Oxygen transfer; P450; Peroxidase

Indexed keywords

1, 2, 4 BENZENETRIOL; 1, 4 BENZOQUINONE; ASCORBIC ACID; BENZENE; BENZOQUINONE; CATECHOL; HYDROQUINONE; OXYGEN; OXYGENASE; PEROXYGENASE; UNCLASSIFIED DRUG;

AGROCYBE AEGERITA; ANALYTIC METHOD; ANIMAL CELL; ARTICLE; ENZYME ISOLATION; ENZYME KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; NONHUMAN; OXIDATION; OXYGENATION; PH; POLYMERIZATION;

EID: 84875065797     PISSN: None     EISSN: 21910855     Source Type: Journal    
DOI: 10.1186/2191-0855-3-5     Document Type: Article

References (38)

1. Albarran G, Boggess W, Rassolov V, Schuler RH: Absorption spectrum, mass spectrometric properties, and electronic structure of 1, 2-benzoquinone. J Phys Chem A 2010, 114(28): 7470-7478.
2. Aranda E, Kinne M, Kluge M, Ullrich R, Hofrichter M: Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases. Appl Microbiol Biotechnol 2009, 82(6): 1057-1066.
3. Bagnéris C, Cammack R, Mason JR: Subtle difference between benzene and toluene dioxygenases of Pseudomonas putida. Appl Environ Microbiol 2005, 71(3): 1570-1580.
4. Barková K, Kinne M, Ullrich R, Hennig L, Fuchs A, Hofrichter M: Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase. Tetrahedron 2011, 67(26): 4874-4878.
5. Bathelt CM, Mulholland AJ, Harvey JN: QM/MM modeling of benzene hydroxylation in human cytochrome P450 2C9†. J Phys Chem A 2008, 112(50): 13149-13156.
6. Colby J, Stirling DI, Dalton H: The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. Biochem J 1977, 165(2): 395-402.
7. de Visser SP, Shaik S: A proton-shuttle mechanism mediated by the porphyrin in benzene hydroxylation by cytochrome P450 enzymes. J Am Chem Soc 2003, 125(24): 7413-7424.
8. Fesenko VV, Gragerov IP: Dokl Akad Nauk SSSR. 1955, 101: 695.
9. Froland WA, Andersson KK, Lee SK, Liu Y, Lipscomb JD: Methane monooxygenase component B and reductase alter the regioselectivity of the hydroxylase component-catalyzed reactions. A novel role for protein-protein interactions in an oxygenase mechanism. J Biol Chem 1992, 267(25): 17588-17597.
10. Fruscella W: Benzene Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc; 2000.
11. Gillard JR, Newlands MJ, Bridson JN, Burnell DJ: π-Facial stereoselectivity in the Diels-Alder reactions of benzene oxides. Can J Chem 1991, 69(9): 1337-1343.
12. Green J, Dalton H: Substrate specificity of soluble methane monooxygenase. Mechanistic implications. J Biol Chem 1989, 264(30): 17698-17703.
13. Hanioka N, Yamamoto M, Tanaka-Kagawa T, Jinno H, Narimatsu S: Functional characterization of human cytochrome P450 2E1 allelic variants: in vitro metabolism of benzene and toluene by recombinant enzymes expressed in yeast cells. Arch Toxicol 2010, 84(5): 363-371.
14. Hernández A, Ruiz MT: An EXCEL template for calculation of enzyme kinetic parameters by non-linear regression. Bioinformatics 1998, 14(2): 227-228.
15. Hofrichter M, Günther T, Fritsche W: Metabolism of phenol, chloro- and nitrophenols by the Penicillium strain Bi 7/2 isolated from a contaminated soil. Biodegradation 1992, 3(4): 415-421.
16. Hofrichter M, Ullrich R, Pecyna M, Liers C, Lundell T: New and classic families of secreted fungal heme peroxidases. Appl Microbiol Biotechnol 2010, 87(3): 871-897.
17. Jindrová E, Chocová M, Demnerová K, Brenner V: Bacterial aerobic degradation of benzene, toluene, ethylbenzene and xylene. Folia Microbiol (Praha) 2002, 47(2): 83-93.
18. Kinne M, Poraj-Kobielska M, Aranda E, Ullrich R, Hammel KE, Scheibner K, Hofrichter M: Regioselective preparation of 5-hydroxypropranolol and 4′-hydroxydiclofenac with a fungal peroxygenase. Bioorg Med Chem Lett 2009, 19(11): 3085-3087.
19. Kinne M, Poraj-Kobielska M, Ralph SA, Ullrich R, Hofrichter M, Hammel KE: Oxidative cleavage of diverse ethers by an extracellular fungal peroxygenase. J Biol Chem 2009, 284(43): 29343-29349.
20. Kluge M, Ullrich R, Dolge C, Scheibner K, Hofrichter M: Hydroxylation of naphthalene by aromatic peroxygenase from Agrocybe aegerita proceeds via oxygen transfer from and intermediary epoxidation. Appl Microbiol Biotechnol 2009, 81(6): 1071-1076.
21. Kluge M, Ullrich R, Scheibner K, Hofrichter M: Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita. Green Chem 2012, 14(2): 440-446.
22. Leahy JG, Batchelor PJ, Morcomb SM: Evolution of the soluble diiron monooxygenases. FEMS Microbiol Rev 2003, 27(4): 449-479.
23. Letzel T, Pöschl U, Wissiack R, Rosenberg E, Grasserbauer M, Niessner R: Phenyl-modified reversed-phase liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry: A universal method for the analysis of partially oxidized aromatic hydrocarbons. Anal Chem 2001, 73(7): 1634-1645.
24. Lovern MR, Turner MJ, Meyer M, Kedderis GL, Bechtold WE, Schlosser PM: Identification of benzene oxide as a product of benzene metabolism by mouse, rat, and human liver microsomes. Carcinogenesis 1997, 18(9): 1695-1700.
25. Peter S, Kinne M, Wang X, Ullrich R, Kayser G, Groves JT, Hofrichter M: Selective hydroxylation of alkanes by an extracellular fungal peroxygenase. FEBS J 2011, 278(19): 3667-3675.
26. Piontek K, Ullrich R, Liers C, Diedrichs K, Plattner AD, Hofrichter M: Crystallization of a 45 kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron. Acta Crystallograph Sect F Struct Biol Cryst Commun 2010, 66: 693-698.
27. Platt KL, Oesch F: The preparation of [14C] and [3H] labelled benzene oxide. J Labelled Compd Radiopharm 1977, 13(4): 471-479.
28. Sala-trepat JM, Evans WC: The meta cleavage of catechol by Azotobacter species. Eur J Biochem 1971, 20(3): 400-413.
29. Seaton MJ, Schlosser PM, Bond JA, Medinsky MA: Benzene metabolism by human liver microsomes in relation to cytochrome P450 2E1 activity. Carcinogenesis 1994, 15(9): 1799-1806.
30. Snyder R, Chepiga T, Yang CS, Thomas H, Platt K, Oesch F: Benzene metabolism by reconstituted cytochromes P450 2B1 and 2E1 and its modulation by cytochrome b5, microsomal epoxide hydrolase, and glutathione transferases: evidence for an important role of microsomal epoxide hydrolase in the formation of hydroquinone. Toxicol Appl Pharmacol 1993, 122(2): 172-181.
31. Tamie N, Rui-Sheng W: Induction of cytochrome P450 by toluene. Int J Biochem 1994, 26(12): 1333-1340.
32. Tao Y, Fishman A, Bentley WE, Wood TK: Oxidation of benzene to phenol, catechol, and 1, 2, 3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1. Appl Environ Microbiol 2004, 70(7): 3814-3820.
33. Ullrich R, Dolge C, Kluge M, Hofrichter M: Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita. FEBS Lett 2008, 582(29): 4100-4106.
34. Ullrich R, Hofrichter M: The haloperoxidase of the agaric fungus Agrocybe aegerita hydroxylates toluene and naphthalene. FEBS Lett 2005, 579(27): 6247-6250.
35. Ullrich R, Nüske J, Scheibner K, Spantzel J, Hofrichter M: Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes. Appl Environ Microbiol 2004, 70(8): 4575-4581.
36. van Tamelen EE: The reaction of cyclohexadiene-1, 4 with electrophilic reagents. J Am Chem Soc 1955, 77(6): 1704-1706.
37. Weber M, Weber M, Kleine-Boymann M: Phenol Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co, KGaA; 2000.
38. Zhou N-Y, Jenkins A, Chan Kwo Chion CKN, Leak DJ: The alkene monooxygenase from Xanthobacter strain Py2 is closely related to aromatic monooxygenases and catalyzes aromatic monohydroxylation of benzene, toluene, and phenol. Appl Environ Microbiol 1999, 65(4): 1589-1595.