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References
Wixtrom, R.N.; Hammock, B.D.: Membrane-bound and soluble-fraction epoxide hydrolases. Biochem. Pharmacol. Toxicol., 1, 1–93 (1985)
Waechter, F.; Merdes, M.; Bieri, F.; Stäubli, W.; Bentley, P.: Purification and characterization of a soluble epoxide hydrolase from rabbit liver. Eur. J. Biochem., 125, 457–461 (1982)
Wang, P.; Meijer, J.; Guengerich, F.P.: Purification of human liver cytosolic epoxide hydrolase and comparison to the microsomal enzyme. Biochemistry, 21, 5769–5776 (1982)
Gill, S.S.: Purification of mouse liver cytosolic epoxide hydrolase. Biochem. Biophys. Res. Commun., 112, 763–769 (1983)
Meijer, J.; Depierre, J.W.: Properties of cytosolic epoxide hydrolase purified from the liver of untreated and clofibrate-treated mice. Purification procedure and physiochemical characterization of the pure enzymes. Eur. J. Biochem., 148, 421–430 (1985)
Prestwich, G.D.; Hammock, B.D.: Rapid purification of cytosolic epoxide hydrolase from normal and clofibrate-treated animals by affinity chromatography. Proc. Natl. Acad. Sci. USA, 82, 1663–1667 (1985)
Meijer, J.; Depierre, J.W.: Properties of cytosolic epoxide hydrolase purified from the liver of untreated and clofibrate-treated mice. Characterization of optimal assay conditions, substrate specificity and effects of modulators on the catalytic activity. Eur. J. Biochem., 150, 7–16 (1985)
Hammock, B.D.; Prestwich, G.D.; Loury, D.N.; Cheung, P.Y.K.; Eng, W.S.; Park, S.K.; Moody, D.E.; Silva, M.H.; Wixtrom, R.N.: Comparison of crude and affinity purified cytosolic epoxide hydrolases from hepatic tissue of control and clofibrate-fed mice. Arch. Biochem. Biophys., 244, 292–309 (1986)
Meijer, J.; DePierre, J.W.: Cytosolic epoxide hydrolase. Chem. Biol. Interact., 64, 207–249 (1988)
Wixtrom, R.N.; Silva, M.H.; Hammock, B.D.: Affinity purification of cytosolic epoxide hydrolase using derivatized epoxy-activated Sepharose gels. Anal. Biochem., 169, 71–80 (1988)
Schladt, L.; Hartman, R.; Woerner, W.; Thomas, H.; Oesch, F.; Purification and characterization of rat-liver cytosolic epoxide hydrolase. Eur. J. Biochem., 176, 31–37 (1988)
Schladt, L.; Thomas, H.; Hartmann, R.; Oesch, F.: Human liver cytosolic epoxide hydrolases. Eur. J. Biochem., 176, 715–723 (1988)
Miki, I.; Shimizu, T.; Seyama, Y.; Kitamura, S.; Yamaguchi, K.; Sano, H.; Ueno, H.; Hiratsuka, A.; Watanabe, T.: Enzymic conversion of 11,12-leukotriene A4 to 11,12-dihydroxy-5, 14-cis-7,9-trans-eicosatetraenoic acid. Purification of an epoxide hydrolase from the guinea pig liver cytosol. J. Biol. Chem., 264, 5799–5805 (1989)
Arand, M.; Wagner, H.; Oesch, F.: Asp333, Asp495, and His523 form the catalytic triad of rat soluble epoxide hydrolase. J. Biol. Chem., 271, 4223–4229 (1996)
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., 270, 7968–7974 (1995)
Blee, F.; Schuber, F.: Occurence of fatty acid epoxide hydrolases in soybean (Glycine max). Biochem. J., 282, 711–714 (1992)
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., 263, 386–395 (1999)
Misawa, E.; Chan Kwo Chion, C.K.C.; Archer, I.V.; Woodland, M.P.; Zhou, N.Z.; Carter, S.F.; Widdowson, D.A.; Leak, D.J.: Characterisation of a catabolic epoxide hydrolase from a Corynebacterium sp.. Eur. J. Biochem., 253, 173–183 (1998)
Chang, C.; Gill, S.S.: Purification and characterization of an epoxide hydrolase from the peroxisomal fraction of mouse liver. Arch. Biochem. Biophys., 285, 276–284 (1991)
Halarnkar, P.P.; Nourooz-Zadeh, J.; Kuwano, E.; Jones, A.D.; Hammock, B.D.: Formation of cyclic products from the diepoxide of long-chain fatty esters by cytosolic epoxide hydrolase. Arch. Biochem. Biophys., 294, 586–593 (1992)
Nourooz-Zadeh, J.; Winder, B.S.; Dietze, E.C.; Giometti, C.S.; Tollaksen, S.L.; Hammock, B.D.: Biochemical characterization of a variant form of cytosolic epoxide hydrolase induced by parental exposure to N-ethyl-N-nitrosurea. Comp. Biochem. Physiol. C, 103, 207–214 (1992)
Dietze, E.C.; Magdalou, J.; Hammock, B.D.: Human and murine cytosolic epoxide hydrolase: Physical and structural properties. Int. J. Biochem., 22, 461–470 (1990)
Morisseau, C.; Beetham, J.K.; Pinot, F.; Debernard, S.; Newman, J.W.; Hammock, B.D.: Cress and potato soluble epoxide hydrolases: purification, biochemical characterization, and comparison to mammalian enzymes. Arch. Biochem. Biophys., 378, 321–332 (2000)
Thomas, H.; Schladt, L.; Doehmer, J.; Knehr, M.; Oesch, F.: Rat and human liver cytosolic epoxide hydrolases: evidence for multiple forms at the level of protein and mRNA. Environ. Health Perspect., 88, 49–55 (1990)
Summerer, S.; Hanano, A.; Utsumi, S.; Arand, M.; Schuber, F.; Blee, E.: Stereochemical features of the hydrolysis of 9,10-epoxystearic acid catalysed by plant and mammalian epoxide hydrolases. Biochem. J., 366, 471–480 (2002)
Rink, R.; Kingma, J.; Lutje Spelberg, J.H.; Janssen, D.B.: Tyrosine residues serve as proteon donor in the catalytic mechanism of epoxide hydrolase from Agrobacterium radiobacter. Biochemistry, 39, 5600–5613 (2000)
Gomez, G.A.; Morisseau, C.; Hammock, B.D.; Christianson, D.W.: Structure of human epoxide hydrolase reveals mechanistic inferences on bifunctional catalysis in epoxide and phosphate ester hydrolysis. Biochemistry, 43, 4716–4723 (2004)
Li, C.; Liu, Q.; Song, X.; Ding, D.; Ji, A.; Qu, Y.: Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp. Biotechnol. Lett., 25, 2113–2116 (2003)
Bellevik, S.; Zhang, J.; Meijer, J.: Brassica napus soluble epoxide hydrolase (BNSEH1). Eur. J. Biochem., 269, 5295–5302 (2002)
Nardini, M.; Rink, R.; Janssen, D.B.; Dijkstra, B.W.: Structure and mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1. J. Mol. Catal. B, 11, 1035–1042 (2001)
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.; Furstoss, R.: Enhancing the enantioselectivity of an epoxide hydrolase by directed evolution. Org. Lett., 6, 177–180 (2004)
Edqvvist, J.; Farbos, I.: A germination-specific epoxide hydrolase from Euphorbia lagascae. Planta, 216, 403–412 (2003)
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, 100, 1558–1563 (2003)
Bellevik, S.; Summerer, S.; Meijer, J.: Overexpression of Arabidopsis thaliana soluble epoxide hydrolase 1 in Pichia pastoris and characterisation of the recombinant enzyme. Protein Expr. Purif., 26, 65–70 (2002)
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., 8, 111–122 (2000)
Monfort, N.; Archelas, A.; Furstoss, R.: Enzymatic transformations. Part 55: Highly productive epoxide hydrolase catalyzed resolution of an azole antifungal key synthon. Tetrahedron, 60, 601–605 (2004)
DuTeaux, S.B.; Newman, J.W.; Morisseau, C.; Fairbairn, E.A.; Jelks, K.; Hammock, B.D.; Miller, M.G.: Epoxide hydrolases in the rat epididymis: possible roles in xenobiotic and endogenous fatty acid metabolism. Toxicol. Sci., 78, 187–195 (2004)
Yu, Z.; Davis, B.B.; Morisseau, C.; Hammock, B.D.; Olson, J.L.; Kroetz, D.L.; Weiss, R.H.: Vascular localization of soluble epoxide hydrolase in the human kidney. Am. J. Physiol., 286, F720–726 (2004)
Shin, J.-H.; Engidawork, E.; Delabar, J.-M.; Lubec, G.: Identification and characterization of soluble epoxide hydrolase in mouse brain by a robust protein biocehmical method. Amino Acids, 28, 63–69 (2005)
Jones, P.D.; Wolf, N.M.; Morisseau, C.; Whetstone, P.; Hock, B.; Hammock, B.D.: Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies. Anal. Biochem., 343, 66–75 (2005)
Morisseau, C.; Hammock, B.D.: Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Annu. Rev. Pharmacol. Toxicol., 45, 311–333 (2005)
Zeldin, D.C.; Wei, S.; Falck, J.R.; Hammock, B.D.; Snapper, J.R.; Capdevila, J.H.: Metabolism of epoxyeicosatrienoic acids by cytosolic epoxide hydrolase: substrate structural determinants of asymmetric acatalysis. Arch. Biochem. Biophys., 316, 443–451 (1995)
Morisseau, C.; Du, G.; Newman, J.W.; Hammock, B.D.: Mechanism of mammalian soluble epoxide hydrolase inhibition by chalcone oxide derivatives. Arch. Biochem. Biophys., 356, 214–228 (1998)
Srivastava, P.K.; Sharma, V.K.; Kalonia, D.S.; Grant, D.F.: Polymorphisms in human soluble epoxide hydrolase: effects on enzyme activity, enzyme stability, and quarternary structure. Arch. Biochem. Biophys., 427, 164–169 (2004)
Arand, M.; Hemmer, H.; Duerk, H.; Barattis, J.; Archelas, A.; Furstoss, R.: Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase. Biochem. J., 344, 273–280 (1999)
Dietze, E.C.; Kuwano, E.; Casa, J.; Hammock, B.D.: Inhibition of cytosolic epoxide hydrolase by trans-3-phenylglycidols. Biochem. Pharmacol., 42, 1163–1175 (1991)
Tran, K.L.; Aronov, P.A.; Tanaka, H.; Newman, J.W.; Hammock, B.D.; Morisseau, C.: Lipid sulfates and sulfonates are allosteric competitive inhibitors of the N-terminal phosphatase activity of the mammalian soluble poxide hydrolase. Biochemistry, 44 12179–12187 (2005)
Lacourciere, G.M.; Armstrong, R.N.: Microsomal ans soluble epoxide hydrolases are members of the same family of C-X bond hydrolase enzymes. Chem. Res. Toxicol., 7, 121–124 (1994)
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 expoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res., 87, 992–998 (2000)
Dietze, E.C.; Stephens J.; Magdalou, J.; Bender, D.M.; Moyer, M.; Fowler, B.; Hammock, B.D.: Inhibition of human and murine cytosolic epoxide hydrolase by group-selective reagents. Comp. Biochem. Physiol. B, 104, 299–308 (1993)
Arahira, M.; Nong, V.H.; Udaka, K.; Fukazawa, C.: Purification, molecular cloning and ethylene-inducible expression of a soluble-type epoxide hydrolase from soybean (Glycine max [L.] Merr.). Eur. J. Biochem., 267, 2649–2657 (2000)
Sellers, K.W.; Sun, C.; Diez-Freire, C.; Waki, H.; Morisseau, C.; Falck, J.R.; Hammock, B.D.; Paton, J.F.; Raizada, M.K.: Novel mechanism of brain soluble epoxide hydrolase-mediated blood pressure regulation in the spontaneously hypertensive rat. FASEB J., 19, 626–628 (2005)
Mullen, R.T.; Trelease, R.N.; Duerk, H.; Arand, M.; Hammock, B.D.; Oesch, F.; Grnat, D.F.: Differential subcellular localization of endogenous and transfected soluble epoxide hydrolase in mammalian cells: evidence for isozyme variants. FEBS Lett., 445 301–305 (1999)
Dietze, E.D.; Kuwano, E.; Hammock, B.D.: The interaction of cytosolic epoxide hydrolase with chiral epoxides. Int. J. Biochem., 25, 43–52 (1993)
Schiott, B.; Bruice, T.C.: Reaction mechanism of soluble epoxide hydrolase: insights from molecular dynamics simulations. J. Am. Chem. Soc., 124, 14558–14570 (2002)
Haeggstroem, J.; Meijer, J.; Radmark, O.: Leukotriene A4. Enzymatic conversion into 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid by mouse liver cytosolic epoxide hydrolase. J. Biol. Chem., 261, 6332–6337 (1986)
Enayetallah, A.E.; French, R.A.; Barber, M.; Grant, D.F.: Cell-specific subcellular localization of soluble epoxide hydrolase in human tissues. J. Histochem. Cytochem., 54, 329–335 (2006)
McElroy, N.R.; Jurs, P.C.: QSAR and classification of murine and human soluble epoxide hydrolase inhibition by urea-like compounds. J. Med. Chem., 46, 1066–1080 (2003)
Stapleton, A.; Beetham, J.K.; Pinot, F.; Garbarino, J.E.; Rockhold, D.R.; Friedman, M.; Hammock, B.D.; Belknap, W.R.: Cloning and expression of soluble epoxide hydrolase from potato. Plant J., 6, 251–258 (1994)
Harris, T.R.; Morisseau, C.; Walzem, R.L.; Ma, S.J.; Hammock, B.D.: The cloning and characterization of a soluble epoxide hydrolase in chicken. Poult. Sci., 85, 278–287 (2006)
Cronin, A.; Mowbray, S.; Duerk, 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, 100, 1552–1557 (2003)
Schmelzer, K.R.; Kubala, L.; Newman, J.W.; Kim, I.-H.; Eiserich, J.P.; Hammock, B.D.: Soluble epoxide hydrolase is a therapeutic target for acute inflammation. Proc. Natl. Acad. Sci. USA, 102, 9772–9777 (2005)
Newman, J.W.; Morisseau, C.; Hammock, B.D.: Epoxide hydrolases: their roles and interactions with lipid metabolism. Prog. Lipid Res., 44, 1–51 (2005)
Gomez, G.A.; Morisseau, C.; Hammock, B.D.; Christianson, D.W.: Human soluble expoxide hydrolase: structural basis of inhibition by 4-(3-cyclohexylureido)-carboxylic acids. Protein Sci., 15, 58–64 (2006)
Ota, K.; Hammock, B.D.: Cytosolic and microsomal epoxide hydrolases: differential properties in mammalian liver. Science, 207, 1479–1480 (1980)
Draper, A.J.; Hammock, B.D.: Inhibition of soluble and microsomal epoxide hydrolase by zinc and other metals. Toxicol. Sci., 52, 26–32 (1999)
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(2009). Soluble epoxide hydrolase. In: Chang, A. (eds) Class 3 Hydrolases. Springer Handbook of Enzymes, vol S5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-85703-7_37
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