Fungal unspecific peroxygenases: Heme-thiolate proteins that combine peroxidase and cytochrome P450 properties

Advances in Experimental Medicine and Biology

Volumn 851, Issue , 2015, Pages 341-368

  Hofrichter, Martin ^a   Kellner, Harald ^a   Pecyna, Marek J ^a   Ullrich, René ^a  

^a International Graduate School Zittau   (Germany)

Author keywords

Compound I; Dealkylation; Epoxidation; Heme thiolate; Hydroxylation; P450 monooxygenase; Peroxidase

Indexed keywords

CHLORIDE PEROXIDASE; CYTOCHROME P450; FUNGAL ENZYME; FUNGAL PROTEIN; HEME THIOLATE PROTEIN; MYELOPEROXIDASE; PEROXIDASE; UNCLASSIFIED DRUG; UNSPECIFIC PEROXYGENASE;

AROMATIZATION; ARTICLE; BASIDIOMYCETES; DEALKYLATION; DECHLORINATION; EPOXIDATION; FAST PROTEIN LIQUID CHROMATOGRAPHY; FUNGAL STRAIN; FUNGUS GROWTH; GLYCOSYLATION; HYDROXYLATION; MOLECULAR PHYLOGENY; NONHUMAN; OOMYCETES; OXYGENATION; PHAGOSOME; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN FUNCTION; PROTEIN PURIFICATION; PROTEIN SYNTHESIS; SULFOXIDATION; CATALYSIS; CHEMISTRY; CLASSIFICATION; ENZYMOLOGY; GENETICS; HUMAN; MARASMIUS; METABOLISM;

AGROCYBE AEGERITA; BASIDIOMYCOTA; COPRINELLUS; FUNGI; MARASMIUS; OOMYCETES; STRAMENOPILES;

CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; FUNGAL PROTEINS; HUMANS; MARASMIUS; PEROXIDASE;

EID: 84930221936     PISSN: 00652598     EISSN: 22148019     Source Type: Book Series    
DOI: 10.1007/978-3-319-16009-2_13     Document Type: Article

References (124)

1. Ishimaru A, Yamazaki I (1977) Hydroperoxidedependent hydroxylation involving "H2O2-reducible hemoprotein" in microsomes of pea seeds. A new type enzyme acting on hydroperoxide and a physiological role of seed lipoxygenase. J Biol Chem 252: 6118-6124.
2. Hanano A, Burcklen M, Flenet M, Ivancich A, Louwagie M, Garin J, Blee E (2006) Plant seed peroxygenase is an original heme-oxygenase with an EF-hand calcium binding motif. J Biol Chem 281: 33140-33151.
3. Lequeu J, Fauconnier ML, Chammai A, Bronner R, Blee E (2003) Formation of plant cuticle: evidence for the occurrence of the peroxygenase pathway. Plant J 36: 155-164.
4. Salazar O, Cirino PC, Arnold FH (2003) Thermostabilization of a cytochrome P450 peroxygenase. ChemBioChem 4: 891-893.
5. Estabrook RW, Martin-Wixtrom C, Saeki Y, Renneberg R, Hildebrandt A, Werringloer J (1984) The peroxidatic function of liver microsomal cytochrome P-450: comparison of hydrogen peroxide and NADPH-catalysed N-demethylation reactions. Xenobiotica 14: 87-104.
6. McCallum GP, Weedon AC, Krug P, Bend JR (1996) Microsomal cytochrome P450 peroxygenase metabolism of arachidonic acid in guinea pig liver. J Pharm Exp Ther 278: 1188-1194.
7. Coon MJ, Vaz AD, Bestervelt LL (1996) Cytochrome P450 2: peroxidative reactions of diversozymes. FASEB J 10: 428-434.
8. Prasad S, Mitra S (2004) Substrate modulates compound I formation in peroxide shunt pathway of Pseudomonas putida cytochrome P450(cam). Biochem Biophys Res Commun 314: 610-614.
9. Nordblom GD, White RE, Coon MJ (1976) Studies on hydroperoxide-dependent substrate hydroxylation by purified liver microsomal cytochrome P-450. Arch Biochem Biophys 175: 524-533.
10. Sakaki T (2012) Practical application of cytochrome P450. Biol Pharm Bull 35: 844-849.
11. Zenser TV, Lakshmi VM, Hsu FF, Davis BB (1999) Peroxygenase metabolism of N-acetylbenzidine by prostaglandin H synthase. Formation of an Nhydroxylamine. J Biol Chem 274: 14850-14856.
12. Kuo HH, Mauk AG (2012) Indole peroxygenase activity of indoleamine 2, 3-dioxygenase. Proc Natl Acad Sci U S A 109: 13966-13971.
13. Yamazaki S, Morioka C, Itoh S (2004) Kinetic evaluation of catalase and peroxygenase activities of tyrosinase. Biochemistry 43: 11546-11553.
14. Matsunaga I, Yamada M, Kusunose E, Miki T, Ichihara K (1998) Further characterization of hydrogen peroxide-dependent fatty acid α-hydroxylase from Sphingomonas paucimobilis. J Biochem 124: 105-110.
15. Lee DS, Yamada A, Sugimoto H, Matsunaga I, Ogura H, Ichihara K, Adachi S, Park SY, Shiro Y (2003) Substrate recognition and molecular mechanism of fatty acid hydroxylation by cytochrome P450 from Bacillus subtilis. Crystallographic, spectroscopic, and mutational studies. J Biol Chem 278: 9761-9767.
16. Matsunaga I, Sumimoto T, Ueda A, Kusunose E, Ichihara K (2000) Fatty acid-specific, regiospecific, and stereospecific hydroxylation by cytochrome P450 (CYP152B1) from Sphingomonas paucimobilis: substrate structure required for α-hydroxylation. Lipids 35: 365-371.
17. Shoji O, Wiese C, Fujishiro T, Shirataki C, Wunsch B, Watanabe Y (2010) Aromatic C-H bond hydroxylation by P450 peroxygenases: a facile colorimetric assay for monooxygenation activities of enzymes based on Russig's blue formation. J Biol Inorg Chem 15: 1109-1115.
18. Fujishiro T, Shoji O, Kawakami N, Watanabe T, Sugimoto H, Shiro Y, Watanabe Y (2012) Chiralsubstrate-assisted stereoselective epoxidation catalyzed by H2O2-dependent cytochrome P450SPα. Chem Asian J 7: 2286-2293.
19. Shoji O, Kunimatsu T, Kawakami N, Watanabe Y (2013) Highly selective hydroxylation of benzene to phenol by wild-type cytochrome P450BM3 assisted by decoy molecules. Angew Chem Int Ed 52: 6606-6610.
20. Gaut JP, Yeh GC, Tran HD, Byun J, Henderson JP, Richter GM, Brennan ML, Lusis AJ, Belaaouaj A, Hotchkiss RS, Heinecke JW (2001) Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis. Proc Natl Acad Sci U S A 98: 11961-11966.
21. Tuynman A, Spelberg JL, Kooter IM, Schoemaker HE, Wever R (2000) Enantioselective epoxidation and carbon-carbon bond cleavage catalyzed by Coprinus cinereus peroxidase and myeloperoxidase. J Biol Chem 275: 3025-3030.
22. Geigert J, Lee TD, Dalietos DJ, Hirano DS, Neidleman SL (1986) Epoxidation of alkenes by chloroperoxidase catalysis. Biochem Biophys Res Commun 136: 778-782.
23. Miller VP, Tschirretguth RA, Ortiz de Montellano P (1995) Chloroperoxidase-catalyzed benzylic hydroxylation. Arch Biochem Biophys 319: 333-340.
24. Colonna S, Gaggero N, Casella L, Carrea G, Pasta P (1992) Chloroperoxidase and hydrogen peroxide: an efficient system for enzymatic enantioselective sulfoxidations. Tetrahedron Asymmetry 3: 95-106.
25. Manoj KM, Hager LP (2001) Utilization of peroxide and its relevance in oxygen insertion reactions catalyzed by chloroperoxidase. Biochim Biophys Acta 1547: 408-417.
26. Zhang R, He Q, Chatfield D, Wang X (2013) Paramagnetic nuclear magnetic resonance relaxation and molecular mechanics studies of the chloroperoxidase-indole complex: insights into the mechanism of chloroperoxidase-catalyzed regioselective oxidation of indole. Biochemistry 52: 3688-3701.
27. Hofrichter M, Ullrich R (2006) Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance. Appl Microbiol Biotechnol 71: 276-288.
28. Stamets P, Chilton JS (1983) The mushroom cultivator: a practical guide to growing mushrooms at home. Agarikon Press, Olympia.
29. IndexFungorum (2013) www. indexfungorum. org.
30. Manzi P, Marconi S, Aguzzi A, Pizzoferrato L (2004) Commercial mushrooms: nutritional quality and effect of cooking. Food Chem 84: 201-206.
31. Ullrich R, Nüske J, Scheibner K, Spantzel J, Hofrichter M (2004) Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes. Appl Environ Microbiol 70: 4575-4581.
32. Ullrich R, Hofrichter M (2005) The haloperoxidase of the agaric fungus Agrocybe aegerita hydroxylates toluene and naphthalene. FEBS Lett 579: 6247-6250.
33. Kluge MG, Ullrich R, Scheibner K, Hofrichter M (2007) Spectrophotometric assay for detection of aromatic hydroxylation catalyzed by fungal haloperoxidase-peroxygenase. Appl Microbiol Biotechnol 75: 1473-1478.
34. Kluge M, Ullrich R, Dolge C, Scheibner K, Hofrichter M (2009) Hydroxylation of naphthalene by aromatic peroxygenase from Agrocybe aegerita proceeds via oxygen transfer from H2O2 and intermediary epoxidation. Appl Microbiol Biotechnol 81: 1071-1076.
35. Ullrich R, Hofrichter M (2007) Enzymatic hydroxylation of aromatic compounds. Cell Mol Life Sci 64: 271-293.
36. Hofrichter M, Ullrich R (2010) New trends in fungal biooxidation. In: Hofrichter M (ed) Industrial applications, 2nd edn. Springer-Verlag, Berlin, pp 425-449.
37. Ullrich R, Dolge C, Kluge M, Hofrichter M (2008) Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita. FEBS Lett 582: 4100-4106.
38. Peter S, Kinne M, Ullrich R, Kayser G, Hofrichter M (2013) Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase. Enzyme Microb Technol 52: 370-376.
39. Ruiz-Dueñas FJ, Martínez AT (2010) Structural and functional features of peroxidases with a potential as industrial biocatalysts. In: Torres E, Ayala M (eds) Biocatalysis based on heme peroxidases as potential industrial biocatalysts, 1st edn. Springer-Verlag, Berlin, pp 37-59.
40. Hofrichter M, Ullrich R, Pecyna MJ, Liers C, Lundell T (2010) New and classic families of secreted fungal heme peroxidases. Appl Microbiol Biotechnol 87: 871-897.
41. Gutiérrez A, Babot ED, Ullrich R, Hofrichter M, Martínez AT, del Río JC (2011) Regioselective oxygenation of fatty acids, fatty alcohols and other aliphatic compounds by a basidiomycete heme-thiolate peroxidase. Arch Biochem Biophys 514: 33-43.
42. Moncalvo J-M, Vilgalys R, Redhead SA, Johnson JE, James TY, Catherine Aime M, Hofstetter V, Verduin SJW, Larsson E, Baroni TJ, Greg Thorn R et al (2002) One hundred and seventeen clades of euagarics. Mol Phyl Evol 23: 357-400.
43. Anh DH, Ullrich R, Benndorf D, Svatos A, Muck A, Hofrichter M (2007) The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation. Appl Environ Microbiol 73: 5477-5485.
44. Aranda E, Kinne M, Kluge M, Ullrich R, Hofrichter M (2009) Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases. Appl Microbiol Biotechnol 82: 1057-1066.
45. Aranda E, Ullrich R, Hofrichter M (2009) Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases. Biodegradation 21: 267-281.
46. Gröbe G, Ullrich R, Pecyna MJ, Kapturska D, Friedrich S, Hofrichter M, Scheibner K (2011) Highyield production of aromatic peroxygenase by the agaric fungus Marasmius rotula. AMB Express 1: 31.
47. Poraj-Kobielska M (2013) Conversion of pharmaceuticals and other drugs by fungal peroxygenases. Ph. D. Thesis, TU Dresden; http://www. ihi-zittau. de/de/dnl/diss_poraj-kobielska_qucosa. 4268. pdf.
48. Poraj-Kobielska M, Kinne M, Ullrich R, Scheibner K, Kayser G, Hammel KE, Hofrichter M (2011) Preparation of human drug metabolites using fungal peroxygenases. Biochem Pharmacol 82: 789-796.
49. Babot ED, del Río JC, Kalum L, Martínez AT, Gutiérrez A (2013) Oxyfunctionalization of aliphatic compounds by a recombinant peroxygenase from Coprinopsis cinerea. Biotechnol Bioeng 110: 2323-2332.
50. Pecyna MJ, Ullrich R, Bittner B, Clemens A, Scheibner K, Schubert R, Hofrichter M (2009) Molecular characterization of aromatic peroxygenase from Agrocybe aegerita. Appl Microbiol Biotechnol 84: 885-897.
51. Nuell MJ, Fang GH, Axley MJ, Kenigsberg P, Hager LP (1988) Isolation and nucleotide sequence of the chloroperoxidase gene from Caldariomyces fumago. J Bacteriol 170: 1007-1011.
52. Richards TA, Soanes DM, Jones MD, Vasieva O, Leonard G, Paszkiewicz K, Foster PG, Hall N, Talbot NJ (2011) Horizontal gene transfer facilitated the evolution of plant parasitic mechanisms in the oomycetes. Proc Natl Acad Sci U S A 108: 15258-15263.
53. Kellner H, Luis P, Pecyna MJ, Barbi F, Kapturska D, Krüger D, Zak DR, Marmeisse R, Vandenbol M, Hofrichter M (2014) Widespread occurrence of expressed fungal secretory peroxidases in forest soils. PLoS One 9(4): e95557. doi: 10. 1371/journal. pone. 0095557.
54. Morin E, Kohler A, Baker AR, Foulongne-Oriol M, Lombard V, Nagy LG, Ohm RA, Patyshakuliyeva A, Brun A, Aerts AL, Bailey AM et al (2012) Genome sequence of the button mushroom Agaricus bisporus reveals mechanisms governing adaptation to a humic-rich ecological niche. Proc Natl Acad Sci U S A 109: 17501-17506.
55. Ullrich R, Liers C, Schimpke S, Hofrichter M (2009) Purification of homogeneous forms of fungal peroxygenase. Biotechnol J 4: 1619-1626.
56. Kinne M, Poraj-Kobielska M, Ullrich R, Nousiainen P, Sipilä J, Scheibner K, Hammel KE, Hofrichter M (2011) Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase. Holzforschung 65: 673-679.
57. Hatakka A, Lundell T, Hofrichter M, Maijala P (2003) Manganese peroxidase and its role in the degradation of wood lignin. In: Mansfield SD, Saddler JN (eds) Applications of enzymes to lignocellulosics, ACS Symposium series, 855th edn. American Chemical Society, Washington DC, pp 230-243.
58. Liers C, Arnstadt T, Ullrich R, Hofrichter M (2011) Patterns of lignin degradation and oxidative enzyme secretion by different wood-and litter-colonizing basidiomycetes and ascomycetes grown on beechwood. FEMS Microbiol Ecol 78: 91-102.
59. Piontek K, Strittmatter E, Ullrich R, Gröbe G, Pecyna MJ, Kluge M, Scheibner K, Hofrichter M, Plattner DA (2013) Structural basis of substrate conversion in a new aromatic peroxygenase: cytochrome P450 functionality with benefits. J Biol Chem 288: 34767-34776.
60. Anh DH (2008) Novel extracellular haloperoxidaseperoxygenases from the coprophilous fungi Coprinus radians and Coprinus verticillatus: production, purification and biochemical characterization. Ph. D. Thesis, International Graduate School of Zittau.
61. Omura T (2005) Heme-thiolate proteins. Biochem Biophys Res Commun 338: 404-409.
62. Piontek K, Ullrich R, Liers C, Diederichs K, Plattner DA, Hofrichter M (2010) Crystallization of a 45 kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron. Acta Crystallogr Sect F: Struct Biol Cryst Commun 66: 693-698.
63. Ullrich V, Kremers P (1977) Multiple forms of cytochrome P450. Arch Toxicol 39: 41-50.
64. Guengerich FP (1993) Metabolic reactions: types of reactions of cytochrome P450 enzymes. In: Schenkman J, Greim H (eds) Cytochrome P450, 1st edn. Springer, Berlin, pp 89-103.
65. Meunier B, de Visser SP, Shaik S (2004) Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes. Chem Rev 104: 3947-3980.
66. Wang X, Peter S, Kinne M, Hofrichter M, Groves JT (2012) Detection and kinetic characterization of a highly reactive heme-thiolate peroxygenase compound I. J Am Chem Soc 134: 12897-12900.
67. Wang X, Peter S, Ullrich R, Hofrichter M, Groves JT (2013) Driving force for oxygen-atom transfer by heme-thiolate enzymes. Angew Chem Int Ed 52: 9238-9241.
68. Peter S, Kinne M, Wang X, Ullrich R, Kayser G, Groves JT, Hofrichter M (2011) Selective hydroxylation of alkanes by an extracellular fungal peroxygenase. FEBS J 278: 3667-3675.
69. Dunford HB (1999) Heme peroxidases. Wiley, New York.
70. Ortiz de Montellano PR, De Voss JJ (2005) Substrate oxidation by cytochrome P450 enzymes. In: Ortiz De Montellano PR (ed) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer Academic/Plenum Publishers, New York, pp 183-245.
71. Manoj KM, Hager LP (2008) Chloroperoxidase, a janus enzyme. Biochemistry 47: 2997-3003.
72. Stone KL, Hoffart LM, Behan RK, Krebs C, Green MT (2006) Evidence for two ferryl species in chloroperoxidase compound II. J Am Chem Soc 128: 6147-6153.
73. Kühnel K, Derat E, Terner J, Shaik S, Schlichting I (2007) Structure and quantum chemical characterization of chloroperoxidase compound 0, a common reaction intermediate of diverse heme enzymes. Proc Natl Acad Sci U S A 104: 99-104.
74. Hersleth HP, Ryde U, Rydberg P, Görbitz CH, Andersson KK (2006) Structures of the high-valent metal-ion haem-oxygen intermediates in peroxidases, oxygenases and catalases. J Inorg Biochem 100: 460-476.
75. Guengerich FP (2007) Mechanisms of cytochrome P450 substrate oxidation: MiniReview. J Biochem Mol Toxicol 21: 163-168.
76. Ortiz de Montellano PR (2010) Catalytic mechanisms of heme peroxidases. In: Torres E, Ayala M (eds) Biocatalysis based on heme peroxidases-peroxidases as potential industrial biocatalysts, 1st edn. Springer-Verlag, Berlin, pp 80-107.
77. Krest CM, Onderko EL, Yosca TH, Calixto JC, Karp RF, Livada J, Rittle J, Green MT (2013) Reactive intermediates in cytochrome P450 catalysis. J Biol Chem 288: 17074-17081.
78. Lewis DFV (2001) Guide to cytochromes P450: structure and function, 2nd edn. Informa Healthcare, London.
79. Kinne M (2010) The extracellular peroxygenase of the agaric fungus Agrocybe aegerita: catalytic properties and physiological background with particular emphasis on ether cleavage. Ph. D. Thesis, International Graduate School of Zittau; http://www. qucosa. de/fileadmin/data/qucosa/documents/6207/Diss_Kinne_final. pdf.
80. Isin EM, Guengerich FP (2008) Substrate binding to cytochromes P450. Anal Bioanal Chem 392: 1019-1030.
81. Peter S (2013) Oxyfunctionalization of alkanes, alkenes and alkynes by unspecific peroxygenase (EC 1. 11. 2. 1). Ph. D. Thesis, TU Dresden; http://www. ihi-zittau. de/de/dnl/dissertation_sebastian_peter. 4267. pdf.
82. de Visser SP, Ogliaro F, Harris N, Shaik S (2001) Multi-state epoxidation of ethene by cytochrome P450: a quantum chemical study. J Am Chem Soc 123: 3037-3047.
83. de Visser SP, Ogliaro F, Shaik S (2001) Stereospecific oxidation by compound I of cytochrome P450 does not proceed in a concerted synchronous manner. Chem Commun 22: 2322-2323.
84. Piontek K, Smith AT, Blodig W (2001) Lignin peroxidase structure and function. Biochem Soc Trans 29: 111-116.
85. Ruiz-Dueñas FJ, Morales M, Garcia E, Miki Y, Martínez MJ, Martínez AT (2009) Substrate oxidation sites in versatile peroxidase and other basidiomycete peroxidases. J Exp Bot 60: 441-452.
86. Kinne M, Poraj-Kobielska M, Ralph SA, Ullrich R, Hofrichter M, Hammel KE (2009) Oxidative cleavage of diverse ethers by an extracellular fungal peroxygenase. J Biol Chem 284: 29343-29349.
87. Poraj-Kobielska M, Kinne M, Ullrich R, Scheibner K, Hofrichter M (2012) A spectrophotometric assay for the detection of fungal peroxygenases. Anal Biochem 421: 327-329.
88. Karich A, Kluge M, Ullrich R, Hofrichter M (2013) Benzene oxygenation and oxidation by the peroxygenase of Agrocybe aegerita. AMB Express 3: 5.
89. Kluge M, Ullrich R, Scheibner K, Hofrichter M (2012) Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita. Green Chem 14: 440-446.
90. Peter S, Karich A, Ullrich R, Gröbe G, Scheibner K, Hofrichter M (2013) Enzymatic one-pot conversion of cyclohexane into cyclohexanone: comparison of four fungal peroxygenases. J Mol Catal B Enz. doi: 10. 1016/j. molcatb. 2013. 1009. 1016.
91. Auclair K, Hu Z, Little DM, Ortiz De Montellano PR, Groves JT (2002) Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2, 5]octane. J Am Chem Soc 124: 6020-6027.
92. Kinne M, Zeisig C, Ullrich R, Kayser G, Hammel KE, Hofrichter M (2010) Stepwise oxygenations of toluene and 4-nitrotoluene by a fungal peroxygenase. Biochem Biophys Res Commun 397: 18-21.
93. Churakova E, Kluge M, Ullrich R, Arends I, Hofrichter M, Hollmann F (2011) Specific photobiocatalytic oxyfunctionalization reactions. Angew Chem Int Ed 50: 10716-10719.
94. Barková K, Kinne M, Ullrich R, Hennig L, Fuchs A, Hofrichter M (2011) Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase. Tetrahedron 67: 4874-4878.
95. Kinne M, Ullrich R, Hammel KE, Scheibner K, Hofrichter M (2008) Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase. Tetrahedron Lett 49: 5950-5953.
96. Poraj-Kobielska M, Atzrodt J, Holla W, Sandvoss M, Gröbe G, Scheibner K, Hofrichter M (2013) Preparation of labeled human drug metabolites and drug-drug interaction-probes with fungal peroxygenases. J Label Comp Radiopharm 56: 513-519.
97. Tien M, Kirk TK (1984) Lignin-degrading enzyme from Phanerochaete chrysosporium: purification, characterization, and catalytic properties of a unique H2O2-requiring oxygenase. Proc Natl Acad Sci U S A 81: 2280-2284.
98. Samuel D, Silver BL (1965) Oxygen isotope exchange reactions of organic compounds. In: Gold V (ed) Advances in physical organic chemistry. Academic Press, New York, pp 123-186.
99. Maurer HH, Kraemer T, Springer D, Staack RF (2004) Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther Drug Monit 26: 127-131.
100. Langtry HD, Markham A (1999) Sildenafil. Drugs 57: 967-989.
101. Horn A (2009) The use of a novel peroxidase from the basidiomycete Agrocybe aegerita as an example of enatioselective sulfoxidation (Der Einsatz einer neuartigen Peroxidase des Basidiomyceten Agrocybe aegerita am Beispiel der enatioselektiven Sulfoxidation). Ph. D. Thesis, University of Rostock, Germany.
102. Kluge M, Ullrich R, Scheibner K, Hofrichter M (2013) Formation of naphthalene hydrates in the enzymatic conversion of 1, 2-dihydronaphthalene by two fungal peroxygenases and subsequent naphthalene formation. J Mol Catal B Enz. doi: 10. 1016/j. molcatb. 2013. 1008. 1017.
103. Akhtar M, Wright JN, Lee-Robichaud P (2011) A review of mechanistic studies on aromatase (CYP19) and 17α-hydroxylase-17, 20-lyase (CYP17). J Steroid Biochem Mol Biol 125: 2-12.
104. Schomburg D, Schomburg I (2013) Class 1, oxidoreductases, EC 1, vol S8, 2nd edn, Springer handbook of enzymes. Springer, Berlin/New York, pp 504-516.
105. Segel IH (1993) Enzyme kinetics: behavior and analysis of rapid equilibrium and steady-state enzyme systems. Wiley, New York.
106. Ullrich R (2008) Some special reactions of Agrocybe aegerita peroxygenase (AaP). Conference proceedings, Tampere (Finland), p 20.
107. Coon MJ (2005) Cytochrome P450: nature's most versatile biological catalyst. Annu Rev Pharmacol Toxicol 45: 1-25.
108. Pelkonen O, Sotaniemi EA, Ahokas JT (1985) Coumarin 7-hydroxylase activity in human liver microsomes. Properties of the enzyme and interspecies comparisons. Br J Clin Pharmacol 19: 59-66.
109. Johnston JB, Ouellet H, Podust LM, Ortiz de Montellano PR (2011) Structural control of cytochrome P450-catalyzed ω-hydroxylation. Arch Biochem Biophys 507: 86-94.
110. Yoshio O, Tadayoshi H, Fronckowiak M, Nobutaka Y, Yarborough C (1987) Aromatase. J Steroid Biochem 27: 781-789.
111. Yarman A, Peng L, Wu Y, Bandodkar A, Gajovic-Eichelmann N, Wollenberger U, Hofrichter M, Ullrich R, Scheibner K, Scheller F (2011) Can peroxygenase and microperoxidase substitute cytochrome P450 in biosensors. Bioanal Rev 3: 67-94.
112. Peng L, Wollenberger U, Kinne M, Hofrichter M, Ullrich R, Scheibner K, Fischer A, Scheller FW (2010) Peroxygenase based sensor for aromatic compounds. Biosens Bioelectron 26: 1432-1436.
113. Kinne M, Poraj-Kobielska M, Aranda E, Ullrich R, Hammel KE, Scheibner K, Hofrichter M (2009) Regioselective preparation of 5-hydroxypropranolol and 40-hydroxydiclofenac with a fungal peroxygenase. Bioorg Med Chem Lett 19: 3085-3087.
114. Sundaramoorthy M, Terner J, Poulos TL (1995) The crystal structure of chloroperoxidase: a heme peroxidase-cytochrome P450 functional hybrid. Structure 3: 1367-1377.
115. Strittmatter E, Liers C, Ullrich R, Wachter S, Hofrichter M, Plattner DA, Piontek K (2013) First crystal structure of a fungal high-redox potential dye-decolorizing peroxidase: substrate interaction sites and long-range electron transfer. J Biol Chem 288: 4095-4102.
116. Dolge C, Sass A, Kayser G, Ullrich R, Hofrichter M (2011) Exploration of rCciAPO1 from Coprinopsis cinerea: first recombinant aromatic peroxygenase. Conference proceedings, Springer: Karlsruhe, p 132.
117. Morris DR, Hager LP (1966) Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein. J Biol Chem 241: 1763-1768.
118. Farrell RL, Murtagh KE, Tien M, Mozuch MD, Kirk TK (1989) Physical and enzymatic properties of lignin peroxidase isoenzymes from Phanerochaete chrysosporium. Enzyme Microb Technol 11: 322-328.
119. Hollenberg PF, Hager LP (1973) The P-450 nature of the carbon monoxide complex of ferrous chloroperoxidase. J Biol Chem 248: 2630-2633.
120. Palcic MM, Rutter R, Araiso T, Hager LP, Dunford HB (1980) Spectrum of chloroperoxidase compound I. Biochem Biophys Res Commun 94: 1123-1127.
121. Imai Y, Matsunaga I, Kusunose E, Ichihara K (2000) Unique heme environment at the putative distal region of hydrogen peroxide-dependent fatty acid α-hydroxylase from Sphingomonas paucimobilis (Peroxygenase P450SPα). J Biochem 128: 189-194.
122. Koo LS, Tschirret-Guth RA, Straub WE, Moënne-Loccoz P, Loehr TM, Ortiz de Montellano PR (2000) The active site of the thermophilic CYP119 from Sulfolobus solfataricus. J Biol Chem 275: 14112-14123.
123. Sheng X, Horner JH, NewcombM (2008) Spectra and kinetic studies of the compound I derivative of cytochrome P450 119. J AmChem Soc 130: 13310-13320.
124. Baciocchi E, Manduchi L, Lanzalunga O (1999) Prochiral selectivity and deuterium kinetic isotope effect in the oxidation of benzyl alcohol catalyzed by chloroperoxidase. Chem Commun 17: 1715-1716.