Biến đổi các hydrocarbon thơm đa vòng, methyl naphthalenes và dibenzofuran bởi hai peroxygenase nấm

Altarawneh M, Kennedy EM, Dlugogorski BZ, Mackie JC (2008) Computational study of the oxidation and decomposition of dibenzofuran under atmospheric conditions 3. J Phys Chem A 112:6960–6967. doi:10.1021/jp800093j 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. doi:10.1128/AEM.00026-07 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. doi:10.1007/s00253-008-1778-6 Ayala M, Robledo NR, Lopez-Munguia A, Vazquez-Duhalt R (2000) Substrate specificity and ionization potential in chloroperoxidase-catalyzed oxidation of diesel fuel. Environ Sci Technol 34:2804–2809. doi:10.1021/es991270o Baek SO, Field RA, Goldstone ME, Kirk PW, Lester JN, Perry R (1991) A review of atmospheric polycyclic aromatic hydrocarbons: sources, fate and behavior. Water Air Soil Poll 60:279–300. doi:10.1007/BF00282628 Bogan BW, Lamar RT, Hammel KE (1996) Fluorene oxidation in vivo by Phanerochaete chrysosporium and in vitro during manganese peroxidase-dependent lipid peroxidation. Appl Environ Microbiol 62:1788–1792 Brown CM, Reisfeld B, Mayeno AN (2008) Cytochromes P450: a structure-based summary of biotransformations using representative substrates. Drug Metab Rev 40:1–100. doi:10.1080/03602530802309742 Cerniglia CE, Yang SK (1984) Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans. Appl Environ Microbiol 47:119–124 Cerniglia CE, Morgan JC, Gibson DT (1979) Bacterial and fungal oxidation of dibenzofuran. Biochem J 180:175–185 Cerniglia CE, Lambert KJ, Miller DW, Freeman JP (1984) Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans. Appl Environ Microbiol 47:111–118 Cerniglia CE, White GL, Heflich RH (1985) Fungal metabolism and detoxification of polycyclic aromatic hydrocarbons. Arch Microbiol 143:105–110. doi:10.1007/BF00411031 Cerniglia CE, Kelly DW, Freeman JP, Miller DW (1986) Microbial metabolism of pyrene. Chem Biol Interact 57:203–216 Chupungarsa K, Thaniyavarnb S, Rerngsamranb P (2009) Polycyclic aromatic hydrocarbons degradation by Agrocybe sp. CU-43 and its fluorene transformation. Int Biodet Biodegr 63:93–99. doi:10.1016/j.ibiod.2008.06.006 Collins PJ, Kotterman M, Field JA, Dobson A (1996) Oxidation of anthracene and benzo[a]pyrene by laccases from Trametes versicolor. Appl Environ Microbiol 62:4563–4567 Eibes G, Cajthaml T, Moreira MT, Feijoo G, Lema JM (2006) Enzymatic degradation of anthracene, dibenzothiophene and pyrene by manganese peroxidase in media containing acetone. Chemosphere 64:408–414. doi:10.1016/j.chemosphere.2005.11.075 Garon D, Krivobok S, Seigle-Murandi F (2000) Fungal degradation of fluorene. Chemosphere 40:91–97. doi:10.1016/S0045-6535(99)00250-7 Gesell M, Hammer E, Mikolasch A, Schauer F (2004) Oxidation and ring cleavage of dibenzofuran by the filamentous fungus Paecilomyces lilacinus. Arch Microbiol 182:51–59. doi:10.1007/s00203-004-0695-z Guengerich FP (1991) Reactions and significance of cytochrome P-450 enzymes. J Biol Chem 266:10019–10022 Hammel KE (1995) Mechanisms for polycyclic aromatic hydrocarbon degradation by ligninolytic fungi. Environ Health Perspect 103(Suppl 5):41–43 Hammel KE, Green B, Gai WZ (1991) Ring fission of anthracene by a eukaryote. Proc Natl Acad Sci USA 88:10605–10608 Hammel KE, Gai WZ, Green B, Moen MA (1992) Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium. Appl Environ Microbiol 58:1832–1838 Hammer E, Krowas D, Schafer A, Specht M, Francke W, Schauer F (1998) Isolation and characterization of a dibenzofuran-degrading yeast: identification of oxidation and ring cleavage products. Appl Environ Microbiol 64:2215–2219 Harford-Cross CF, Carmichael AB, Allan FK, England PA, Rouch DA, Wong LL (2000) Protein engineering of cytochrome P-450(cam) (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Protein Eng 13:121–128 Harvey RG (1991) Polycyclic aromatic hydrocarbons: chemistry and carcinogenicity. Cambridge Monographs on Cancer Research. Cambridge Hofrichter M, Ullrich R (2006) Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance. Appl Microbiol Biotechnol 71:276–288. doi:10.1007/s00253-006-0417-3 Isin EM, Guengerich FP (2008) Substrate binding to cytochromes P450. Anal Bioanal Chem 392:1019–1030. doi:10.1007/s00216-008-2244-0 Johannes C, Majcherczyk A, Huttermann A (1996) Degradation of anthracene by laccase of Trametes versicolor in the presence of different mediator compounds. Appl Microbiol Biotechnol 46:313–317. doi:10.1007/s002530050823 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. doi:10.1007/s00253-007-0942-8 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. doi:10.1007/s00253-008-1704-y Kotterman MJJ, Heessels E, Jong E, Field JA (1994) The physiology of anthracene biodegradation by the white-rot fungus Bjerkandera sp. strain BOS55. Appl Microbiol Biotechnol 42:179–186. doi:10.1007/BF00170243 Lambert M, Kremer S, Sterner O, Anke H (1994) Metabolism of pyrene by the basidiomycete Crinipellis stipitaria and identification of pyrenequinones and their hydroxylated precursors in strain JK375. Appl Environ Microbiol 60:3597–3601 Liu JZ, Wang M (2007) Improvement of activity and stability of chloroperoxidase by chemical modification. BMC Biotechnol 18:7–23. doi:10.1186/1472-6750-7-23 Manoj KM, Hager LP (2008) Chloroperoxidase, a janus enzyme. Biochemistry 47:2997–3003. doi:10.1021/bi7022656 Manoj KM, Yi X, Rai GP, Hager LP (1999) A kinetic epoxidation assay for chloroperoxidase. Biochem Biophys Res Commun 266:301–303. doi:10.1006/bbrc.1999.1810 Marques HL (2007) Insights into porphyrin chemistry provided by the microperoxidases, the haempeptides derived from cytochrome c. Dalton Trans 39:4371–4385 Miura R, Honmaru S, Nakazaki M (1968) The absolute configurations of the metabolites of naphthalene and phenanthrene in mammalian systems. Tetrahedron Lett 50:5271–5274 Murata Y, Denda A, Maruyama H, Konishi Y (1993) Chronic toxicity and carcinogenicity studies of 1-methylnaphthalene in B6C3F1 mice. Fundam Appl Toxicol 21:44–51. doi:10.1006/faat.1993.1070 Nassar MN, Nesarikar VN, Lozano R, Parker WL, Huang Y, Palaniswamy V, Xu W, Khaselev N (2004) Influence of formaldehyde impurity in polysorbate 80 and PEG-300 on the stability of a parenteral formulation of BMS-204352: identification and control of the degradation product. Pharm Dev Technol 9:189–195. doi:10.1081/PDT-120030249 Neujahr HY, Gaal A (1973) Phenol hydroxylase from yeast. Purification and properties of the enzyme from Trichosporon cutaneum. Eur J Biochem 35:386–400. doi:10.1111/j.1432-1033.1973.tb02851.x Omura T (1999) Forty years of cytochrome P450. Biochem Biophys Res Commun 266:690–698. doi:10.1006/bbrc.1999.1887 Omura T (2005) Heme-thiolate proteins. Biochem Biophys Res Commun 338:404–409. doi:10.1016/j.bbrc.2005.08.267 Osman AM, Koerts J, Boersma MG, Boeren S, Veeger C, Rietjens IM (1996) Microperoxidase/H2O2-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism. Eur J Biochem 240:232–238. doi:10.1111/j.1432-1033.1996.0232h.x Park JB, Clark DS (2006) New reaction system for hydrocarbon oxidation by chloroperoxidase. Biotechnol Bioeng 94:189–192. doi:10.1002/bit.20769 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. doi:10.1007/s00253-009-2000-1 Pothuluri JV, Freeman JP, Evans FE, Cerniglia CE (1993) Biotransformation of fluorene by the fungus Cunninghamella elegans. Appl Environ Microbiol 59:1977–1980 Sack U, Heinze TM, Deck J, Cerniglia CE, Martens R, Zadrazil F, Fritsche W (1997a) Comparison of phenanthrene and pyrene degradation by different wood-decaying fungi. Appl Environ Microbiol 63:3919–3925 Sack U, Hofrichter M, Fritsche W (1997b) Degradation of polycyclic aromatic hydrocarbons by manganese peroxidase of Nematoloma frowardii. FEMS Microbiol Lett 152:227–234. doi:10.1002/jobm.3620370408 Shimada T (2006) Xenobiotic-metabolizing enzymes involved in activation and detoxification of carcinogenic polycyclic aromatic hydrocarbons. Drug Metab Pharmacokinet 21:257–276. doi:10.2133/dmpk.21.257 Sohl CD, Isin EM, Eoff RL, Marsch GA, Stec DF, Guengerich FP (2008) Cooperativity in oxidation reactions catalyzed by cytochrome P450 1A2: highly cooperative pyrene hydroxylation and multiphasic kinetics of ligand binding. J Biol Chem 283:7293–7308. doi:10.1074/jbc.M709783200 Steffen KT, Hatakka A, Hofrichter M (2002) Removal and mineralization of polycyclic aromatic hydrocarbons by litter-decomposing basidiomycetous fungi. Appl Microbiol Biotechnol 60:212–217. doi:10.1007/s00253-002-1105-6 Sutherland JB, Selby AL, Freeman JP, Evans FE, Cerniglia CE (1991) Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl Environ Microbiol 57:3310–3316 Torres E, Bustos-Jaimes I, Le Borgne S (2003) Potential use of oxidative enzymes for the detoxification of organic pollutants. Appl Catal B Environ 46:1–15. doi:10.1016/S0926-3373(03)00228-5 Ullrich R, Hofrichter M (2005) The haloperoxidase of the agaric fungus Agrocybe aegerita hydroxylates toluene and naphthalene. FEBS Lett 579:6247–6250. doi:10.1016/j.febslet.2005.10.014 Ullrich R, Hofrichter M (2007) Enzymatic hydroxylation of aromatic compounds. Cell Mol Life Sci 64:271–293. doi:10.1007/s00018-007-6362-1 Ullrich R, Nuske 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. doi:10.1128/AEM.70.8.4575-4581.2004 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. doi:10.1016/j.febslet.2008.11.006 Vaillancourt FH, Bolin JT, Eltis LD (2006) The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol 41:241–267. doi:10.1080/10409230600817422 Yang SK (1988) Stereoselectivity of cytochrome P-450 isozymes and epoxide hydrolase in the metabolism of polycyclic aromatic hydrocarbons. Biochem Pharmacol 37:61–70. doi:10.1016/0006-2952(88)90755-1 Zhang D, Yang Y, Leakey JE, Cerniglia CE (1996) Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Microbiol Lett 138:221–226. doi:10.1111/j.1574-6968.1996.tb08161.x