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Original Articles

Molecular structural characteristics governing biocatalytic chlorination of PAHs by Chloroperoxidase from Caldariomyces fumago

Pages 159-167 | Received 24 Oct 2003, Accepted 28 Feb 2004, Published online: 01 Feb 2007

References

  • Chen , JW , Peijnenburg , WJGM , Quan , X and Yang , FL . 2000 . Quantitative structure-property relationships for direct photolysis quantum yields of selected polycyclic aromatic hydrocarbons . Sci. Total Environ. , 246 : 11 – 20 .
  • Chen , JW , Peijnenburg , WJGM , Quan , X , Chen , S , Martens , D , Schramm , K-W and Kettrup , A . 2001 . Is it possible to develop a QSPR model for direct photolysis half-lives of PAHs under irradiation of sunlight? . Environ. Pollut. , 114 : 137 – 143 .
  • Chen , JW , Quan , X , Yan , Y , Yang , FL and Peijnenburg , WJGM . 2001 . Quantitative structure-property relationship studies on direct photolysis of selected polycyclic aromatic hydrocarbons in atmospheric aerosol . Chemosphere , 42 : 263 – 270 .
  • Niu , JF , Chen , JW , Martens , D , Quan , X , Yang , FL , Kettrup , A and Schramm , K-W . 2003 . Photolysis of polycyclic aromatic hydrocarbons adsorbed on spruce (Picea abies . Environ. Pollut. , 123 : 39 – 45 .
  • Grimmer G 1983 Environmental Carcinogens: Polycyclic Aromatic Hydrocarbons, Chemistry, Occurrence, Biochemistry, Carcinogenicity CRC Press, Inc. New York
  • Fouillet , B , Chambon , P , Casegnaro , M and Weill , N . 1991 . Effects of ozonation on mutagenic activity of polycyclic aromatic hydrocarbons . Bull. Environ. Contam. Toxicol. , 47 : 1 – 7 .
  • Jocob , J . 1996 . The significance of polycyclic aromatic hydrocarbons as environmental carcinogens . Pure Appl. Chem. , 68 : 301 – 308 .
  • Colmsjo , A , Rannug , A and Rannug , U . 1984 . Some chloro derivatives of polycyclic aromatic hydrocarbons are potent mutagens in Salmonella typhimurium . Mutat. Res. , 135 : 21 – 29 .
  • Beach , AC and Harmon , HJ . 1992 . Additive effects and potential inhibitory mechanism of some common aromatic pollutants on in vitro . J. Biochem. Toxicol. , 7 : 155 – 161 .
  • Gustafsson , E , Brunstrom , B and Nilsson , U . 1994 . Lethality and EROD-inducing potency of chlorinated chrysene in chick embryos . Chemosphere , 29 : 2301 – 2308 .
  • Vollenbroek , EG , Simons , LH , van Schijndel , JW , Barnett , P , Balzar , M , Dekker , H , van der Linden , C and Wever , R . 1995 . Vanadium chloroperoxidases occur widely in nature . Biochem. Soc. Trans. , 23 : 267 – 271 .
  • van Pee , KH , Keller , S , Wage , T , Wynands , I , Schnerr , H and Zehner , S . 2000 . Enzymatic halogenation catalyzed via a catalytic triad and by oxidoreductases . Biol. Chem. , 381 : 1 – 5 .
  • Neidleman , SL . 1975 . Microbial halogenation . CRC Crit. Rev. Microbiol. , 3 : 333 – 358 .
  • Miller , JW and Uden , PC . 1983 . Characterization of non-volatile aqueous chlorination products of humic substances . Environ. Sci. Technol. , 17 : 150 – 157 .
  • Christman , RF , Norwood , DL , Millington , DS , Johnson , JD and Stevens , AA . 1983 . Identity and yields of major halogenated products of aquatic fulvic acid chlorination . Environ. Sci. Technol. , 17 : 625 – 628 .
  • Svenson , A , Kjeller , L-O and Rappe , C . 1989 . Enzyme-mediated formation of 2,3,7,8-tetrasubstituted chlorinated dibenzodioxins and dibenzofurans . Environ. Sci. Technol. , 23 : 900 – 902 .
  • Silk , PJ , Longergan , GC , Arsenault , TL and Boyle , CD . 1997 . Evidence of natural organochlorine formation in peat bogs . Chemosphere , 35 : 2865 – 2880 .
  • Vázquez-Duhalt , R , Ayala , M and Márquez-Rocha , FJ . 2001 . Biocatalytic chlorination of aromatic hydrocarbons by chloroperoxidase of Caldariomyces fumago . Phytochemistry , 58 : 929 – 933 .
  • Sundaramoorthy , M , Terner , J and Poulos , TL . 1995 . The crystal structure of chloroperoxidase: a heme peroxidase-cytochrome P450 functional hybrid . Structure , 3 : 1367 – 1377 .
  • Hammel , KE , Kalyanaraman , B and Kirk , TK . 1986 . Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]dioxins by Phanerochaete chrysosporium . J. Biol. Chem. , 261 : 16948 – 16952 .
  • Vázquez-Duhalt , R , Westlake , DWS and Fedorak , PM . 1994 . Lignin peroxidase oxidation of aromatic compounds in systems containing organic solvents . Appl. Environ. Microbiol. , 60 : 459 – 466 .
  • Bogan , BW and Lamar , RT . 1995 . One-electron oxidation in the degradation of creosote polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium . Appl. Environ. Microbiol. , 61 : 2631 – 2635 .
  • Ayala , M , Robledo , NR , Lopez-Munguia , A and Vázquez-Duhalt , R . 2000 . Substrate specificity and ionization potential in chloroperoxidase-catalyzed oxidation of diesel fuel . Environ. Sci. Technol. , 34 : 2804 – 2809 .
  • Liang , C and Gallagher , DA . 1998 . QSPR prediction of vapor pressure from solely theoretically-derived descriptors . J. Chem. Inf. Comput. Sci. , 38 : 321 – 324 .
  • McClelland , HE and Jurs , PC . 2000 . Quantitative structure-property relationships for the prediction of vapor pressures of organic compounds from molecular structures . J. Chem. Inf. Comput. Sci. , 40 : 967 – 975 .
  • Yaffe , D and Cohen , Y . 2001 . Neural networks based temperature-dependent quantitative structure property relations (QSPRs) for predicting vapor pressure of hydrocarbons . J. Chem. Inf. Comput. Sci. , 41 : 463 – 477 .
  • Chen , JW , Kong , LR , Zhu , CM , Huang , QG and Wang , LS . 1996 . Correlation between photolysis rate constants of polycyclic aromatic hydrocarbons and frontier molecular orbital energy . Chemosphere , 33 : 1143 – 1150 .
  • Chen , JW , Peijnenburg , WJGM , Quan , X , Zhao , YZ , Xue , DM and Yang , FL . 1998 . The application of quantum chemical and statistical technique in developing quantitative structure-property relationships for the photohydrolysis quantum yields of substituted aromatic halides . Chemosphere , 37 : 1169 – 1186 .
  • Wold , S , Sjöström , M and Eriksson , L . 2001 . PLS-regression: a basic tool of chemometrics . Chemom. Intell. Lab. Syst. , 58 : 109 – 130 .
  • Chen , JW , Yang , P , Chen , S , Quan , X , Yuan , X , Schramm , K-W and Kettrup , A . 2003 . Quantitative structure-property relationships for vapor pressures of polybrominated diphenyl ethers . SAR QSAR Environ. Res. , 14 : 97 – 111 .
  • Seward , JR , Cronin , MTD and Schultz , TW . 2002 . The effect of precision of molecular orbital descriptors on toxicity modeling of selected pyridines . SAR QSAR Environ. Res. , 13 : 325 – 340 .
  • Stewart , JJP . 1989 . Optimization of parameters for semiempirical methods I. Method . J. Comput. Chem. , 10 : 209 – 220 .
  • Stewart , JJP . 1989 . Optimization of parameters for semiempirical methods II. Applications . J. Comput. Chem. , 10 : 221 – 264 .
  • Baker , J . 1986 . An algorithm for the location of transition states . J. Comput. Chem. , 7 : 385 – 395 .
  • Pearson , PG . 1986 . Absolute electronegativity and hardness correlated with molecular orbital theory . Proc. Natl Acad. Sci. , 83 : 8440 – 8441 .
  • Faucon , JC , Bureau , R , Faisant , J , Briens , F and Rault , S . 1999 . Predicting of the fish acute toxicity from heterogeneous data coming from notification files . Chemosphere , 38 : 3261 – 3276 .
  • Veith , GD , Mekenyan , OG , Ankley , GT and Call , DJ . 1995 . A QSAR analysis of substitutent effects on the photoinduced acute toxicity of PAHs . Chemosphere , 30 : 2129 – 2142 .
  • Boese , BL , Lamberson , JO , Swartz , RC , Ozretich , R and Cole , F . 1998 . Photoinduced toxicity of PAHs and alkylated PAHs to a marine infaunal amphipod (Rhepoxynius abronius . Arch. Environ. Contam. Toxicol. , 34 : 235 – 240 .
  • Mekenyan , OG , Ankley , GT , Veith , GD and Call , DJ . 1995 . QSARs for photoinduced toxicity of aromatic compounds . SAR QSAR Environ. Res. , 4 : 139 – 145 .
  • Zhao , HM , Chen , JW , Quan , X , Yang , FL and Peijnenburg , WJGM . 2001 . Quantitative structure-property relationship study on reductive dehalogenation of selected halogenated aliphatic hydrocarbons in sediment slurries . Chemosphere , 44 : 1557 – 1563 .

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