The Telltale Structures of Epoxide Hydrolases

References

• Arand M., Oesch F. Mammalian xenobiotic epoxide hydrolases. Enzyme Systems that Metabolise Drugs and Other Xenobiotics, C. Ioannides. John Wiley & Sons Ltd. 2002; pp. 459–483
   Google Scholar
• Arand M., Knehr M., Thomas H., Zeller H.-D., Oesch F. An impaired peroxisomal targeting sequence leading to an unusual bicompartmental distribution of cytosolic epoxide hydrolase. FEBS Lett. 1991; 294: 19–22
   PubMed Web of Science ®Google Scholar
• Arand M., Grant D. F., Beetham J. K., Friedberg T., Oesch F., Hammock B. D. Sequence similarity of mammalian epoxide hydrolases to the bacterial haloalkane dehalogenase and other related proteins. Implication for the potential catalytic mechanism of enzymatic epoxide hydrolysis. FEBS Lett. 1994; 338: 251–256
   PubMed Web of Science ®Google Scholar
• Arand M., Wagner H., Oesch F. Asp333, Asp495, and His523 form the catalytic triad of rat soluble epoxide hydrolase. J. Biol. Chem. 1996; 271: 4223–4229
   PubMed Web of Science ®Google Scholar
• Arand M., Hemmer H., Dürk H., Baratti J., Archelas A., Furstoss R., Oesch F. Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase. Biochem. J. 1999a; 344: 273–280
   PubMed Web of Science ®Google Scholar
• Arand M., Müller F., Mecky A., Hinz W., Urban P., Pompon D., Kellner R., Oesch F. Catalytic triad of microsomal epoxide hydrolase: replacement of Glu404 with Asp leads to a strongly increased turnover rate. Biochem. J. 1999b; 337: 37–43
   PubMed Web of Science ®Google Scholar
• Arand M., Hallberg B. M., Zou J., Bergfors T., Oesch F., van der Werf M. J., De Bont J. A., Jones T. A., Mowbray S. L. Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site. EMBO J. 2003a; 22: 2583–2592
   PubMed Web of Science ®Google Scholar
• Arand M., Herrero Plana M. E., Hengstler J. G., Lohmann M., Cronin A., Oesch F. Detoxification strategy of epoxide hydrolase—the basis for a threshold in chemical carcinogenesis. EXCLI J. 2003b; 2: 22–30
   Google Scholar
• Argiriadi M. A., Morisseau C., Hammock B. D., Christianson D. W. Detoxification of environmental mutagens and carcinogens: structure, mechanism, and evolution of liver epoxide hydrolase. Proc. Natl. Acad. Sci. USA 1999; 96: 10637–10642
   PubMed Web of Science ®Google Scholar
• Argiriadi M. A., Morisseau C., Goodrow M. H., Dowdy D. L., Hammock B. D., Christianson D. W. Binding of alkylurea inhibitors to epoxide hydrolase implicates active site tyrosines in substrate activation. J. Biol. Chem. 2000; 275: 15265–15270
   PubMed Web of Science ®Google Scholar
• Armstrong R. N., Cassidy C. S. New structural and chemical insight into the catalytic mechanism of epoxide hydrolases. Drug Metab. Rev. 2000; 32: 327–338
   PubMed Web of Science ®Google Scholar
• Barbirato F., Verdoes J. C., de Bont J. A., van der Werf M. J. The Rhodococcus erythropolis DCL14 limonene-1,2-epoxide hydrolase gene encodes an enzyme belonging to a novel class of epoxide hydrolases. FEBS Lett. 1998; 438: 293–296
   PubMed Web of Science ®Google Scholar
• Beetham J. K., Tian T., Hammock B. D. cDNA cloning and expression of a soluble epoxide hydrolase from human liver. Arch. Biochem. Biophys. 1993; 305: 197–201
   PubMed Web of Science ®Google Scholar
• Beetham J. K., Grant D., Arand M., Garbarino J., Kiyosue T., Pinot F., Oesch F., Belknap W. R., Shinozaki K., Hammock B. D. Gene evolution of epoxide hydrolases and recommended nomenclature. DNA Cell Biol. 1995; 14: 61–71
   PubMed Web of Science ®Google Scholar
• Cronin A., Mowbray S., Dürk H., Homburg S., Fleming I., Fisslthaler B., Oesch F., Arand M. The N-terminal domain of mammalian soluble epoxide hydrolase is a phosphatase. Proc. Natl. Acad. Sci. USA 2003; 100: 1552–1557
   PubMed Web of Science ®Google Scholar
• Dimmeler S., Fleming I., Fisslthaler B., Hermann C., Busse R., Zeiher A. M. Activation of nitric oxide synthase in endothelial cells by Akt-dependent phosphorylation. Nature 1999; 399: 601–605
   PubMed Web of Science ®Google Scholar
• Fang X., Kaduce T. L., Weintraub N. L., Harmon S., Teesch L. M., Morisseau C., Thompson D. A., Hammock B. D., Spector A. A. Pathways of epoxyeicosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition. J. Biol. Chem. 2001; 276: 14867–14874
   PubMed Web of Science ®Google Scholar
• Franken S. M., Rozeboom H. J., Kalk K. H., Dijkstra B. W. Crystal structure of haloalkane dehalogenase: an enzyme to detoxify halogenated alkanes. EMBO J. 1991; 10: 1297–1302
   PubMed Web of Science ®Google Scholar
• Fretland A. J., Omiecinski C. J. Epoxide hydrolases: biochemistry and molecular biology. Chem. Biol. Interact. 2000; 129: 41–59
   PubMed Web of Science ®Google Scholar
• Funk C. D., Radmark O., Fu J. Y., Matsumoto T., Jornvall H., Shimizu T., Samuelsson B. Molecular cloning and amino acid sequence of leukotriene A4 hydrolase. Proc. Natl. Acad. Sci. USA 1987; 84: 6677–6681
   PubMed Web of Science ®Google Scholar
• Grant D. F., Storms D. H., Hammock B. D. Molecular cloning and expression of murine liver soluble epoxide hydrolase. J. Biol. Chem. 1993; 268: 17628–17633
   PubMed Web of Science ®Google Scholar
• Hammock B. D., Pinot F., Beetham J. K., Grant D. F., Arand M. E., Oesch F. Isolation of a putative hydroxyacyl enzyme intermediate of an epoxide hydrolase. Biochem. Biophys. Res. Commun. 1994; 198: 850–856
   PubMed Web of Science ®Google Scholar
• Hammock B., Storms D., Grant D. Epoxide hydrolases. Comprehensive Toxicology, F. Guengerich. Pergamon Press, Oxford 1997; pp. 283–305
   Google Scholar
• Heinemann F. S., Ozols J. The covalent structure of microsomal epoxide hydrolase. II. The complete amino acid sequence. J. Biol. Chem. 1984; 259: 797–804
   PubMed Web of Science ®Google Scholar
• Janssen D. B., Fries F., van der Ploeg J., Kazemier B., Terpstra P., Witholt B. Cloning of 1,2-dichloroethane degradation genes of Xanthobacter autotrophicus GJ10 and expression and sequencing of the dhlA gene. J. Bacteriol. 1989; 171: 6791–6799
   PubMed Web of Science ®Google Scholar
• Knehr M., Thomas H., Arand M., Gebel T., Zeller H. D., Oesch F. Isolation and characterization of a cDNA encoding rat liver cytosolic epoxide hydrolase and its functional expression in. Escherichia coli. J. Biol. Chem. 1993; 268: 17623–17627
   PubMed Web of Science ®Google Scholar
• Koonin E. V., Tatusov R. L. Computer analysis of bacterial haloacid dehalogenases defines a large superfamily of hydrolases with diverse specificity—application of an iterative approach to database search. J. Mol. Biol. 1994; 244: 125–132
   PubMed Web of Science ®Google Scholar
• Lacourciere G. M., Armstrong R. N. The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate. J. Am. Chem. Soc. 1993; 115: 10466–10467
   Web of Science ®Google Scholar
• Lacourciere G. M., Armstrong R. N. Microsomal and soluble epoxide hydrolases are members of the same family of C–X bond hydrolase enzymes. Chem. Res. Toxicol. 1994; 7: 121–124
   PubMed Web of Science ®Google Scholar
• Laughlin L. T., Tzeng H. F., Lin S., Armstrong R. N. Mechanism of microsomal epoxide hydrolase. Semifunctional site-specific mutants affecting the alkylation half-reaction. Biochemistry 1998; 37: 2897–2904
   PubMed Web of Science ®Google Scholar
• Moghaddam M. F., Grant D. F., Cheek J. M., Greene J. F., Williamson K. C., Hammock B. D. Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase. Nat. Med. 1997; 3: 562–566
   PubMed Web of Science ®Google Scholar
• Morisseau C., Archelas A., Guitton C., Faucher D., Furstoss R., Baratti J. C. Purification and characterization of a highly enantioselective epoxide hydrolase from. Aspergillus niger. Eur. J. Biochem. 1999; 263: 386–395
   PubMedGoogle Scholar
• Müller F., Arand M., Frank H., Seidel A., Hinz W., Winkler L., Hänel K., Blee E., Beetham J. K., Hammock B. D., Oesch F. Visualization of a covalent intermediate between microsomal epoxide hydrolase, but not cholesterol epoxide hydrolase, and their substrates. Eur. J. Biochem. 1997; 245: 490–496
   PubMedGoogle Scholar
• Nardini M., Ridder I. S., Rozeboom H. J., Kalk K. H., Rink R., Janssen D. B., Dijkstra B. W. The x-ray structure of epoxide hydrolase from Agrobacterium radiobacter AD1. An enzyme to detoxify harmful epoxides. J. Biol. Chem. 1999; 274: 14579–14586
   PubMed Web of Science ®Google Scholar
• Newman J. W., Morisseau C., Harris T. R., Hammock B. D. The soluble epoxide hydrolase encoded by EPXH2 is a bifunctional enzyme with novel lipid phosphate phosphatase activity. Proc. Natl. Acad. Sci. USA 2003; 100: 1558–1563
   PubMed Web of Science ®Google Scholar
• Oesch F. Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 1973; 3: 305–340
   PubMed Web of Science ®Google Scholar
• Ollis D. L., Cheah E., Cygler M., Dijkstra B., Frolow F., Franken S. M., Harel M., Remington S. J., Silman I., Schrag J., Sussman J. L., Verschueren K. H. G., Goldman A. The α/β hydrolase fold. Protein Eng. 1992; 5: 197–211
   PubMedGoogle Scholar
• Pinot F., Grant D. F., Beetham J. K., Parker A. G., Borhan B., Landt S., Jones A. D., Hammock B. D. Molecular and biochemical evidence for the involvement of the Asp-333-His-523 pair in the catalytic mechanism of soluble epoxide hydrolase. J. Biol. Chem. 1995; 270: 7968–7974
   PubMed Web of Science ®Google Scholar
• Pries F., Kingma J., Pentenga M., Vanpouderoyen G., Jeronimusstratingh C. M., Bruins A. P., Janssen D. B. Site-directed mutagenesis and oxygen isotope incorporation studies of the nucleophilic aspartate of haloalkane dehalogenase. Biochemistry 1994; 33: 1242–1247
   PubMed Web of Science ®Google Scholar
• Ridder I. S., Rozeboom H. J., Kalk K. H., Janssen D. B., Dijkstra B. W. Three-dimensional structure of l-2-haloacid dehalogenase from Xanthobacter autotrophicus GJ10 complexed with the substrate-analogue formate. J. Biol. Chem. 1997; 272: 33015–33022
   PubMed Web of Science ®Google Scholar
• Rink R., Janssen D. B. Kinetic mechanism of the enantioselective conversion of styrene oxide by epoxide hydrolase from Agrobacterium radiobacter AD1. Biochemistry 1998; 37: 18119–18127
   PubMed Web of Science ®Google Scholar
• Rink R., Fennema M., Smids M., Dehmel U., Janssen D. B. Primary structure and catalytic mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1. J. Biol. Chem. 1997; 272: 14650–14657
   PubMed Web of Science ®Google Scholar
• Rink R., Kingma J., Lutje Spelberg J. H., Janssen D. B. Tyrosine residues serve as proton donor in the catalytic mechanism of epoxide hydrolase from. Agrobacterium radiobacter. Biochemistry 2000; 39: 5600–5613
   PubMed Web of Science ®Google Scholar
• Rudberg P. C., Tholander F., Thunnissen M. M., Samuelsson B., Haeggstrom J. Z. Leukotriene A4 hydrolase: selective abrogation of leukotriene B4 formation by mutation of aspartic acid 375. Proc. Natl. Acad. Sci. USA 2002; 99: 4215–4220
   PubMed Web of Science ®Google Scholar
• Sinal C. J., Miyata M., Tohkin M., Nagata K., Bend J. R., Gonzalez F. J. Targeted disruption of soluble epoxide hydrolase reveals a role in blood pressure regulation. J. Biol. Chem. 2000; 275: 40504–40510
   PubMed Web of Science ®Google Scholar
• Thunnissen M. M., Nordlund P., Haeggstrom J. Z. Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation. Nat. Struct. Biol. 2001; 8: 131–135
   PubMedGoogle Scholar
• Tzeng H.-F., Laughlin L. T., Lin S., Armstrong R. N. The catalytic mechanism of microsomal epoxide hydrolase involves reversible formation and rate-limiting hydrolysis of the alkyl-enzyme intermediate. J. Am. Chem. Soc. 1996; 118: 9436–9437
   Web of Science ®Google Scholar
• Tzeng H.-F., Laughlin L. T., Armstrong R. N. Semifunctional site-specific mutants affecting the hydrolytic half-reaction of microsomal epoxide hydrolase. Biochemistry 1998; 37: 2905–2911
   PubMed Web of Science ®Google Scholar
• van der Werf M. J., Overkamp K. M., de Bont J. A. Limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14 belongs to a novel class of epoxide hydrolases. J. Bacteriol. 1998; 180: 5052–5057
   PubMed Web of Science ®Google Scholar
• van der Werf M. J., Swarts H. J., de Bont J. A. Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. Appl. Environ. Microbiol. 1999; 65: 2092–2102
   PubMed Web of Science ®Google Scholar
• Verschueren K. H. G., Seljée F., Rozeboom H. J., Kalk K. H., Dijkstra B. W. Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase. Nature 1993; 363: 693–698
   PubMed Web of Science ®Google Scholar
• Yamada T., Morisseau C., Maxwell J. E., Argiriadi M. A., Christianson D. W., Hammock B. D. Biochemical evidence for the involvement of tyrosine in epoxide activation during the catalytic cycle of epoxide hydrolase. J. Biol. Chem. 2000; 275: 23082–23088
   PubMed Web of Science ®Google Scholar
• Yu Z., Xu F., Huse L. M., Morisseau C., Draper A. J., Newman J. W., Parker C., Graham L., Engler M. M., Hammock B. D., Zeldin D. C., Kroetz D. L. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res. 2000; 87: 992–998
   PubMed Web of Science ®Google Scholar
• Zheng J., Plopper C. G., Lakritz J., Storms D. H., Hammock B. D. Leukotoxin-diol: a putative toxic mediator involved in acute respiratory distress syndrome. Am. J. Respir. Cell Mol. Biol. 2001; 25: 434–438
   PubMed Web of Science ®Google Scholar
• Zou J., Hallberg B. M., Bergfors T., Oesch F., Arand M., Mowbray S. L., Jones T. A. Structure of Aspergillus niger epoxide hydrolase at 1.8 A resolution: implications for the structure and function of the mammalian microsomal class of epoxide hydrolases. Structure Fold. Des. 2000; 8: 111–122
   Google Scholar