Epoxide hydrolases: Structure, function, mechanism, and assay

Methods in Enzymology

Volumn 400, Issue , 2005, Pages 569-588

  Arand, Michael ^a   Cronin, Annette ^a   Adamska, Magdalena ^a   Oesch, Franz ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE HYDROLASE; FOSX ENZYME; LEUKOTRIENE A4 HYDROLASE; LIMONENE EPOXIDE HYDROLASE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

CATALYSIS; DETOXIFICATION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME STRUCTURE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVIEW;

ANIMALS; BIOLOGICAL ASSAY; EPOXIDE HYDROLASES; HUMANS; METABOLIC DETOXICATION, DRUG; MOLECULAR STRUCTURE; PROTEIN FOLDING; RECOMBINANT PROTEINS; STEARIC ACIDS; XENOBIOTICS;

EID: 30144442042     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(05)00032-7     Document Type: Review

References (67)

1. Arand M., Cronin A., Oesch F., Mowbray S.L., and Jones T.A. The telltale structures of epoxide hydrolases Drug Metab. Rev. 35 2003 365 383
2. Arand M., Grant D.F., Beetham J.K., Friedberg T., Oesch F., and 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. 338 1994 251 256
3. Arand M., Hallberg B.M., Zou J.Y., Bergfors T., Oesch F., van der Werf M.J., de Bont J.A.M., Jones T.A., and Mowbray S.L. Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site EMBO J. 22 2003 2583 2592
4. Arand M., Hemmer H., Dürk H., Baratti J., Archelas A., Furstoss R., and Oesch F. Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase Biochem. J. 344 1999 273 280
5. Arand M., Müller F., Mecky A., Hinz W., Urban P., Pompon D., Kellner R., and Oesch F. Catalytic triad of microsomal epoxide hydrolase: Replacement of Glu(404) with Asp leads to a strongly increased turnover rate Biochem. J. 337 1999 37 43
6. Arand M., Wagner H., and Oesch F. Asp(333), Asp(495), and His(523) form the catalytic triad of rat soluble epoxide hydrolase J. Biol. Chem. 271 1996 4223 4229
7. Archelas A., and Furstoss R. Epoxide hydrolases: New tools for the synthesis of fine organic chemicals Trends Biotechnol. 16 1998 108 116
8. Argiriadi M.A., Morisseau C., Hammock B.D., and Christianson D.W. Detoxification of environmental mutagens and carcinogens: Structure, mechanism, and evolution of liver epoxide hydrolase Proc. Natl. Acad. Sci. USA 96 1999 10637 10642
9. Barbirato F., Verdoes J.C., de Bont J.A.M., and 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. 438 1998 293 296
10. Barth S., Fischer M., Schmid R.D., and Pleiss J. Sequence and structure of epoxide hydrolases: A systematic analysis Proteins 55 2004 846 855
11. Beetham J.K., Tian T.G., and Hammock B.D. cDNA cloning and expression of a soluble epoxide hydrolase from human liver Arch. Biochem. Biophys. 305 1993 197 201
12. Bell P.A., and Kasper C.B. Expression of rat microsomal epoxide hydrolase in Escherichia coli: Identification of a histidyl residue essential for catalysis J. Biol. Chem. 268 1993 14011 14017
13. Bentley W.E., Kebede B., Franey T., and Wang M.Y. Segregated characterization of recombinant epoxide hydrolase synthesis via the baculovirus-insect cell expression system Chem. Eng. Sci. 49 1994 4133 4141
14. Cole S.T., Brosch R., Parkhill J., Garnier T., Churcher C., Harris D., Gordon S.V., Eiglmeier K., Gas S., Barry C.E. 3rd, Tekaia F., Badcock K., Basham D., Brown D., Chillingworth T., Connor R., Davies R., Devlin K., Feltwell T., Gentles S., Hamlin N., Holroyd S., Hornsby T., Jagels K., and Barrell B.G. Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence Nature 393 1998 537 544
15. Cronin A., Mowbray S., Dürk H., Homburg S., Fleming I., Fisslthaler B., Oesch F., and Arand M. The N-terminal domain of mammalian soluble epoxide hydrolase is a phosphatase Proc. Natl. Acad. Sci. USA 100 2003 1552 1557
16. de Vries E.J., and Janssen D.B. Biocatalytic conversion of epoxides Curr. Opin. Biotechnol. 14 2003 414 420
17. Eugster H.P., Sengstag C., Hinnen A., Meyer U.A., and Würgler F.E. Heterologous expression of human microsomal epoxide hydrolase in Saccharomyces cerevisiae: Study of the valpromide carbamazepine epoxide interaction Biochem. Pharmacol. 42 1991 1367 1372
18. Fillgrove K.L., Pakhomova S., Newcomer M.E., and Armstrong R.N. Mechanistic diversity of fosfomycin resistance in pathogenic microorganisms J. Am. Chem. Soc. 125 2003 15730 15731
19. Frantz S.W., van den Eeckhout E., Sinsheimer J.E., Yoshihara M., and Koreeda M. Mutagenicity in Salmonella assays of cyclohexane epoxide derivatives Toxicol. Lett. 25 1985 265 271
20. Friedberg T., Becker R., Oesch F., and Glatt H. Studies on the importance of microsomal epoxide hydrolase in the detoxification of arene oxides using the heterologous expression of the enzyme in mammalian cells Carcinogenesis 15 1994 171 175
21. Gautier J.C., Urban P., Beaune P., and Pompon D. Engineered yeast-cells as model to study coupling between human xenobiotic metabolizing enzymes: Simulation of the 2 1st steps of benzo[a]pyrene activation Eur. J. Biochem. 211 1993 63 72
22. Genzel Y., Archelas A., Broxterman Q.B., Schulze B., and Furstoss R. Microbial transformations 50: Selection of epoxide hydrolases for enzymatic resolution of 2-, 3- or 4-pyridyloxirane J. Mol. Cat. B Enz. 16 2002 217 222
23. Guengerich F.P. Epoxide hydrolase: Properties and metabolic roles Rev. Biochem. Toxicol. 4 1982 5 30
24. Haeggstrom J.Z. Leukotriene A(4) hydrolase/aminopeptidase, the gatekeeper of chemotactic leukotriene B(4) biosynthesis J. Biol. Chem. 279 2004 50639 50642
25. Haeggstrom J.Z., Wetterholm A., Vallee B.L., and Samuelsson B. Leukotriene A4 hydrolase: An epoxide hydrolase with peptidase activity Biochem. Biophys. Res. Commun. 173 1990 431 437
26. Hammock B.D., Gill S.S., Stamoudis V., and Gilbert L.I. Soluble mammalian epoxide hydratase: Action on juvenile hormone and other terpenoid epoxides Comp. Biochem. Physiol. B 53 1976 263 265
27. Hammock B.D., Storms D., and Grant D. Epoxide hydrolases F.P. Guengerich "Comprehensive Toxicology" 1997 Pergamon Press Oxford 283 305
28. Herrero M.E., Arand M., Hengstler J.G., and Oesch F. Recombinant expression of human microsomal epoxide hydrolase protects V79 Chinese hamster cells from styrene oxide, but not from ethylene oxide-induced DNA strand breaks Environ. Mol. Mutagen. 30 1997 429 439
29. Hosagrahara V.P., Rettie A.E., Hassett C., and Omiecinski C.J. Functional analysis of human microsomal epoxide hydrolase genetic variants Chem.- Biol. Interact. 150 2004 149 159
30. Jerina D.M., and Daly J.W. Arene oxides: A new aspect of drug metabolism Science 185 1974 573 582
31. Johansson P., Unge T., Cronin A., Arand M., Bergfors T., Jones T.A., and Mowbray S.L. Structure of an atypical epoxide hydrolase from Mycobacterium tuberculosis gives insights into its function J. Mol. Biol. 351 2005 1048 1056
32. Kim M.H., Geacintov N.E., Pope M., and Harvey R.G. Structural effects in reactivity and adduct formation of polycyclic aromatic epoxide and diol epoxide derivatives with DNA: Comparison between 1-oxiranylpyrene and benzo[a]pyrenediol epoxide Biochemistry 23 1984 5433 5439
33. Knehr M., Thomas H., Arand M., Gebel T., Zeller H.D., and Oesch F. Isolation and characterization of a cDNA encoding rat liver cytosolic epoxide hydrolase and its functional expression in Escherichia coli J. Biol. Chem. 268 1993 17623 17627
34. Lacourciere G.M., and Armstrong R.N. Microsomal and soluble epoxide hydrolases are members of the same family of C-X bond hydrolase enzymes Chem. Res. Toxicol. 7 1994 121 124
35. McGee J., and Fitzpatrick F. Enzymatic hydration of leukotriene A4: Purification and characterization of a novel epoxide hydrolase from human erythrocytes J. Biol. Chem. 260 1985 12832 12837
36. 4 hydrolase is a zinc-containing aminopeptidase Biochem. Biophys. Res. Commun. 173 1990 620 623
37. Misawa E., Chion C., Archer I.V., Woodland M.P., Zhou N.Y., Carter S.F., Widdowson D.A., and Leak D.J. Characterisation of a catabolic epoxide hydrolase from a Corynebacterium sp Eur. J. Biochem. 253 1998 173 183
38. Miyata M., Kudo G., Lee Y.H., Yang T.J., Gelboin H.V., Fernandez-Salguero P., Kimura S., and Gonzalez F.J. Targeted disruption of the microsomal epoxide hydrolase gene: Microsomal epoxide hydrolase is required for the carcinogenic activity of 7,12-dimethylbenz[a]anthracene J. Biol. Chem. 274 1999 23963 23968
39. Moghaddam M.F., Grant D.F., Cheek J.M., Greene J.F., Williamson K.C., and Hammock B.D. Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase Nature Med. 3 1997 562 566
40. Monterde M.I., Lombard M., Archelas A., Cronin A., Arand M., and Furstoss R. Enzymatic transformations. 58: Enantioconvergent biohydrolysis of styrene oxide derivatives catalysed by the Solanum tuberosum epoxide hydrolase Tetrahedron Asymmetry 15 2004 2801 2805
41. Müller F., Arand M., Frank H., Seidel A., Hinz W., Winkler L., Hänel K., Blée E., Beetham J.K., Hammock B.D., and Oesch F. Visualization of a covalent intermediate between microsomal epoxide hydrolase, but not cholesterol epoxide hydrolase, and their substrates Eur. J. Biochem. 245 1997 490 496
42. Nardini M., Ridder I.S., Rozeboom H.J., Kalk K.H., Rink R., Janssen D.B., and Dijkstra B.W. The x-ray structure of epoxide hydrolase from Agrobacterium radiobacter AD1: An enzyme to detoxify harmful epoxides J. Biol. Chem. 274 1999 14579 14586
43. Newman J.W., Morisseau C., Harris T.R., and 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 100 2003 1558 1563
44. Oesch F. Mammalian epoxide hydrases: Inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds Xenobiotica 3 1973 305 340
45. Oesch F., Jerina D.M., and Daly J. A radiometric assay for hepatic epoxide hydrase activity with [7-3H]styrene oxide Biochim. Biophys. Acta 227 1971 685 691
46. Oesch F., Timms C.W., Walker C.H., Guenthner T.M., Sparrow A., Watabe T., and Wolf C.R. Existence of multiple forms of microsomal epoxide hydrolase with radically different substrate specifities Carcinogenesis 5 1984 7 9
47. Ota K., and Hammock B.D. Cytosolic and microsomal epoxide hydrolases: Differential properties in mammalian liver Science 207 1980 1479 1481
48. Pries F., Kingma J., Pentenga M., Vanpouderoyen G., Jeronimusstratingh C.M., Bruins A.P., and Janssen D.B. Site-directed mutagenesis and oxygen isotope incorporation studies of the nucleophilic aspartate of haloalkane dehalogenase Biochemistry 33 1994 1242 1247
49. Raijmakers M.T.M., de Galan-Roosen T.E.M., Schilders G.W., Merkus J., Steegers E.A.P., and Peters W.H.M. The Tyr113His polymorphism in exon 3 of the microsomal epoxide hydrolase gene is a risk factor for perinatal mortality Acta Obstet. Gynecol. Scand. 83 2004 1056 1060
50. Reetz M.T., Torre C., Eipper A., Lohmer R., Hermes M., Brunner B., Maichele A., Bocola M., Arand M., Cronin A., Genzel Y., Archelas A., and Furstoss R. Enhancing the enantioselectivity of an epoxide hydrolase by directed evolution Org. Lett. 6 2004 177 180
51. Rink R., Fennema M., Smids M., Dehmel U., and Janssen D.B. Primary structure and catalytic mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1 J. Biol. Chem. 272 1997 14650 14657
52. Sandberg M., Hassett C., Adman E.T., Meijer J., and Omiecinski C.J. Identification and functional characterization of human soluble epoxide hydrolase genetic polymorphisms J. Biol. Chem. 275 2000 28873 28881
53. Sato K., Emi M., Ezura Y., Fujita Y., Takada D., Ishigami T., Umemura S., Xin Y.P., Wu L.L., Larrinaga-Shum S., Stephenson S.H., Hunt S.C., and Hopkins P.N. Soluble epoxide hydrolase variant (Glu287Arg) modifies plasma total cholesterol and triglyceride phenotype in familial hypercholesterolemia: Intrafamilial association study in an eight-generation hyperlipidemic kindred J. Hum. Genet. 49 2004 29 34
54. Sims P., Grover P.L., Swaisland A., Pal K., and Hewer A. Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide Nature 252 1974 326 328
55. Sinal C.J., Miyata M., Tohkin M., Nagata K., Bend J.R., and Gonzalez F.J. Targeted disruption of soluble epoxide hydrolase reveals a role in blood pressure regulation J. Biol. Chem. 275 2000 40504 40510
56. Smith C.A.D., and Harrison D.J. Association between polymorphism in gene for microsomal epoxide hydrolase and susceptibility to emphysema Lancet 350 1997 630 633
57. Spector A.A., Fang X., Snyder G.D., and Weintraub N.L. Epoxyeicosatrienoic acids (EETs): Metabolism and biochemical functions Prog. Lipid Res. 43 2004 55 90
58. Steinreiber A., and Faber K. Microbial epoxide hydrolases for preparative biotransformations Curr. Opin. Biotechnol. 12 2001 552 558
59. Thunnissen M., Nordlund P., and Haeggstrom J.Z. Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation Nat. Struct. Biol. 8 2001 131 135
60. van der Werf M.J., Overkamp K.M., and de Bont J.A.M. Limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14 belongs to a novel class of epoxide hydrolases J. Bacteriol. 180 1998 5052 5057
61. van der Werf M.J., Swarts H.J., and de Bont J.A.M. Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene Appl. Environ. Microbiol. 65 1999 2092 2102
62. van Loo B., Spelberg J.H.L., Kingma J., Sonke T., Wubbolts M.G., and Janssen D.B. Directed evolution of epoxide hydrolase from A-radiobacter toward higher enantioselectivity by error-prone PCR and DNA shuffling Chem. Biol. 11 2004 981 990
63. Visser H., Vreugdenhil S., de Bont J.A.M., and Verdoes J.C. Cloning and characterization of an epoxide hydrolase-encoding gene from Rhodotorula glutinis Appl. Microbiol. Biotechnol. 53 2000 415 419
64. Wahler D., and Reymond J.-L. The adrenaline test for enzymes Angew. Chem. Int. Ed. 41 2002 1229 1232
65. Wickliffe J.K., Ammenheuser M.M., Salazar J.J., Abdel-Rahman S.Z., Hastings-Smith D.A., Postlethwait E.M., Lloyd R.S., and Word J.B. A model of sensitivity: 1,3-Butadiene increases mutant frequencies and genomic damage in mice lacking a functional microsomal epoxide hydrolase gene Environ. Mol. Mutagen. 42 2003 106 110
66. 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., and Kroetz D.L. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids Circ. Res. 87 2000 992 998
67. Zou J.Y., Hallberg B.M., Bergfors T., Oesch F., Arand M., Mowbray S.L., and Jones T.A. Structure of Aspergillus niger epoxide hydrolase at 1.8 angstrom resolution: Implications for the structure and function of the mammalian microsomal class of epoxide hydrolases Structure 8 2000 111 122