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Research Article

The Telltale Structures of Epoxide Hydrolases

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Pages 365-383 | Published online: 12 Aug 2003

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Read on this site (3)

Malliga R. Iyer, Biswajit Kundu & Casey M. Wood. (2022) Soluble epoxide hydrolase inhibitors: an overview and patent review from the last decade. Expert Opinion on Therapeutic Patents 32:6, pages 629-647.
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Gary P. Carlson. (2010) Metabolism and Toxicity of Styrene in Microsomal Epoxide Hydrolase-Deficient Mice. Journal of Toxicology and Environmental Health, Part A 73:24, pages 1689-1699.
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Margherita Strolin Benedetti, Rhys Whomsley, Italo Poggesi, Willi Cawello, François-Xavier Mathy, Marie-Laure Delporte, Peggy Papeleu & Jean-Baptiste Watelet. (2009) Drug metabolism and pharmacokinetics. Drug Metabolism Reviews 41:3, pages 344-390.
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Articles from other publishers (52)

Rui Huang, Chuang Li, Shi-Guang Zhao, Qing-Tao Liu, Yan Liu & Zheng-Lian Xue. (2023) Enantioconvergent hydrolysis of racemic 1,2-epoxypentane and 1,2-epoxyhexane by an engineered Escherichia coli strain overexpressing a novel Streptomyces fradiae epoxide hydrolase. Enzyme and Microbial Technology 166, pages 110228.
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Vijaya P. Godase, Navnath M. Kumbhar, Sanjay P. Govindwar & Ameeta Ravi Kumar. (2023) Characterization reveals a putative epoxide hydrolase from Yarrowia lipolytica with the ability to convert rac-1,2-epoxyhexane to (R)-diol. Process Biochemistry 125, pages 248-258.
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Thodhal-Yoganandham Suman, Soo-Yeon Kim, Dong-Hyuk Yeom & Junho Jeon. (2022) Transformation Products of Emerging Pollutants Explored Using Non-Target Screening: Perspective in the Transformation Pathway and Toxicity Mechanism—A Review. Toxics 10:2, pages 54.
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Songyang Han, Jiaxin Chen, Yujie Zhao, Hongsheng Cai & Changhong Guo. (2021) Bacillus subtilis HSY21 can reduce soybean root rot and inhibit the expression of genes related to the pathogenicity of Fusarium oxysporum. Pesticide Biochemistry and Physiology 178, pages 104916.
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Téo Hebra, Nicolas Elie, Salomé Poyer, Elsa Van Elslande, David Touboul & Véronique Eparvier. (2021) Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks. Metabolites 11:7, pages 444.
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Chen Zhang, Chuang Li, Xiu-xiu Zhu, You-yi Liu, Jun Zhao & Min-chen Wu. (2020) Highly regio- and enantio-selective hydrolysis of two racemic epoxides by GmEH3, a novel epoxide hydrolase from Glycine max. International Journal of Biological Macromolecules 164, pages 2795-2803.
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Morteza Sarparast, Devon Dattmore, Jamie Alan & Kin Sing Stephen Lee. (2020) Cytochrome P450 Metabolism of Polyunsaturated Fatty Acids and Neurodegeneration. Nutrients 12:11, pages 3523.
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Eike C. Schulz, Sara R. Henderson, Boris Illarionov, Thomas Crosskey, Stacey M. Southall, Boris Krichel, Charlotte Uetrecht, Markus Fischer & Matthias Wilmanns. (2020) The crystal structure of mycobacterial epoxide hydrolase A. Scientific Reports 10:1.
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Jan S. Kramer, Stefano Woltersdorf, Thomas Duflot, Kerstin Hiesinger, Felix F. Lillich, Felix Knöll, Sandra K. Wittmann, Franca-M. Klingler, Steffen Brunst, Apirat Chaikuad, Christophe Morisseau, Bruce D. Hammock, Carola Buccellati, Angelo Sala, G. Enrico Rovati, Matthieu Leuillier, Sylvain Fraineau, Julie Rondeaux, Victor Hernandez-Olmos, Jan Heering, Daniel Merk, Denys Pogoryelov, Dieter Steinhilber, Stefan Knapp, Jeremy Bellien & Ewgenij Proschak. (2019) Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain. Journal of Medicinal Chemistry 62:18, pages 8443-8460.
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Julian Zaugg, Yosephine Gumulya, Mikael Bodén, Alan E. Mark & Alpeshkumar K. Malde. (2018) Effect of Binding on Enantioselectivity of Epoxide Hydrolase. Journal of Chemical Information and Modeling 58:3, pages 630-640.
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A. Marowsky & M. Arand. 2018. Comprehensive Toxicology. Comprehensive Toxicology 308 325 .
Jan Kramer & Ewgenij Proschak. (2017) Phosphatase activity of soluble epoxide hydrolase. Prostaglandins & Other Lipid Mediators 133, pages 88-92.
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Samantha L. Hoopes, Artiom Gruzdev, Matthew L. Edin, Joan P. Graves, J. Alyce Bradbury, Gordon P. Flake, Fred B. Lih, Laura M. DeGraff & Darryl C. Zeldin. (2017) Generation and characterization of epoxide hydrolase 3 (EPHX3)-deficient mice. PLOS ONE 12:4, pages e0175348.
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Maria E. S. Lind & Fahmi Himo. (2016) Quantum Chemical Modeling of Enantioconvergency in Soluble Epoxide Hydrolase. ACS Catalysis 6:12, pages 8145-8155.
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Christopher D. Bahl, Kelli L. Hvorecny, Christophe Morisseau, Scott A. Gerber & Dean R. Madden. (2016) Visualizing the Mechanism of Epoxide Hydrolysis by the Bacterial Virulence Enzyme Cif. Biochemistry 55:5, pages 788-797.
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Konstantia Gkarmiri, Roger D. Finlay, Sadhna Alström, Elizabeth Thomas, Marc A. Cubeta & Nils Högberg. (2015) Transcriptomic changes in the plant pathogenic fungus Rhizoctonia solani AG-3 in response to the antagonistic bacteria Serratia proteamaculans and Serratia plymuthica. BMC Genomics 16:1.
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Patricio Godoy & Mario Aranda. (2015) Highlight report: epoxide hydrolases?protection from reactive compounds and risk of cardiovascular disease. Archives of Toxicology 89:12, pages 2463-2464.
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Sean D. Kodani & Bruce D. Hammock. (2015) The 2014 Bernard B. Brodie Award Lecture—Epoxide Hydrolases: Drug Metabolism to Therapeutics for Chronic Pain. Drug Metabolism and Disposition 43:5, pages 788-802.
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Ahmed A. El-Sherbeni & Ayman O. S. El-Kadi. (2014) The role of epoxide hydrolases in health and disease. Archives of Toxicology 88:11, pages 2013-2032.
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Jiangbo Du, Zhiyu Ma, Yifan Zhang, Ting Wang, Xiaoyan Chen & Dafang Zhong. (2014) Simultaneous determination of ornidazole and its main metabolites in human plasma by LC–MS/MS: application to a pharmacokinetic study. Bioanalysis 6:18, pages 2343-2356.
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Qing-Qing Zhu, Wan-Hong He, Xu-Dong Kong, Li-Qiang Fan, Jian Zhao, Su-Xia Li & Jian-He Xu. (2013) Heterologous overexpression of Vigna radiata epoxide hydrolase in Escherichia coli and its catalytic performance in enantioconvergent hydrolysis of p-nitrostyrene oxide into (R)-p-nitrophenyl glycol. Applied Microbiology and Biotechnology 98:1, pages 207-218.
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Weixin Zhao, Jianfeng Luo & Xuwei Cai. (2013) Association between microsomal epoxide hydrolase 1 polymorphisms and susceptibility to esophageal cancer: a meta-analysis. Tumor Biology 34:4, pages 2383-2388.
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Siwen Wang, Jie Zhu, Ruxin Zhang, Siyang Wang & Zongheng Gu. (2013) Association between microsomal epoxide hydrolase 1 T113C polymorphism and susceptibility to lung cancer. Tumor Biology 34:2, pages 1045-1052.
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Martina Decker, Magdalena Adamska, Annette Cronin, Francesca Di Giallonardo, Julia Burgener, Anne Marowsky, John R. Falck, Christophe Morisseau, Bruce D. Hammock, Artiom Gruzdev, Darryl C. Zeldin & Michael Arand. (2012) EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides. Journal of Lipid Research 53:10, pages 2038-2045.
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Åsa Janfalk Carlsson, Paul Bauer, Huan Ma & Mikael Widersten. (2012) Obtaining Optical Purity for Product Diols in Enzyme-Catalyzed Epoxide Hydrolysis: Contributions from Changes in both Enantio- and Regioselectivity. Biochemistry 51:38, pages 7627-7637.
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Timo FrömelBenno Jungblut, Jiong HuCaroline TrouvainEduardo Barbosa-SicardRüdiger PoppStefan Liebner, Stefanie DimmelerBruce D. Hammock & Ingrid Fleming. (2012) Soluble epoxide hydrolase regulates hematopoietic progenitor cell function via generation of fatty acid diols. Proceedings of the National Academy of Sciences 109:25, pages 9995-10000.
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Richard LonsdaleSimon HoyleDaniel T. GreyLars Ridder & Adrian J. Mulholland. (2012) Determinants of Reactivity and Selectivity in Soluble Epoxide Hydrolase from Quantum Mechanics/Molecular Mechanics Modeling. Biochemistry 51:8, pages 1774-1786.
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Jonathan W. Nelson & Nabil J. Alkayed. 2012. Translational Stroke Research. Translational Stroke Research 277 294 .
Annette Cronin, Martina Decker & Michael Arand. (2011) Mammalian soluble epoxide hydrolase is identical to liver hepoxilin hydrolase. Journal of Lipid Research 52:4, pages 712-719.
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Giorgia Saga, Alejandro Giorgetti, Christian Fufezan, Giorgio M. Giacometti, Roberto Bassi & Tomas Morosinotto. (2010) Mutation Analysis of Violaxanthin De-epoxidase Identifies Substrate-binding Sites and Residues Involved in Catalysis. Journal of Biological Chemistry 285:31, pages 23763-23770.
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Diana Lindberg, Mario de la Fuente Revenga & Mikael Widersten. (2010) Temperature and pH Dependence of Enzyme-Catalyzed Hydrolysis of trans -Methylstyrene Oxide. A Unifying Kinetic Model for Observed Hysteresis, Cooperativity, and Regioselectivity . Biochemistry 49:10, pages 2297-2304.
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Mikael Widersten, Ann Gurell & Diana Lindberg. (2010) Structure?function relationships of epoxide hydrolases and their potential use in biocatalysis. Biochimica et Biophysica Acta (BBA) - General Subjects 1800:3, pages 316-326.
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Diana Lindberg, Shabbir Ahmad & Mikael Widersten. (2010) Mutations in salt-bridging residues at the interface of the core and lid domains of epoxide hydrolase StEH1 affect regioselectivity, protein stability and hysteresis. Archives of Biochemistry and Biophysics 495:2, pages 165-173.
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A. Marowsky, A. Cronin, F. Frère, M. Adamska & M. Arand. 2010. Comprehensive Toxicology. Comprehensive Toxicology 275 294 .
John A. Timbrell & Timothy C. Marrs. 2009. General and Applied Toxicology. General and Applied Toxicology.
Martina Decker, Michael Arand & Annette Cronin. (2009) Mammalian epoxide hydrolases in xenobiotic metabolism and signalling. Archives of Toxicology 83:4, pages 297-318.
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Wolfgang Dekant. 2009. Molecular, Clinical and Environmental Toxicology. Molecular, Clinical and Environmental Toxicology 57 86 .
Diana Lindberg, Adolf Gogoll & Mikael Widersten. (2008) Substrate‐dependent hysteretic behavior in StEH1‐catalyzed hydrolysis of styrene oxide derivatives. The FEBS Journal 275:24, pages 6309-6320.
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Annette Cronin, Shirli Homburg, Heike Dürk, Ingrid Richter, Magdalena Adamska, Frederic Frère & Michael Arand. (2008) Insights into the Catalytic Mechanism of Human sEH Phosphatase by Site-Directed Mutagenesis and LC–MS/MS Analysis. Journal of Molecular Biology 383:3, pages 627-640.
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Ann Thomaeus, Agata Naworyta, Sherry L. Mowbray & Mikael Widersten. (2008) Removal of distal protein-water hydrogen bonds in a plant epoxide hydrolase increases catalytic turnover but decreases thermostability. Protein Science 17:7, pages 1275-1284.
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Ding Ai, Yi Fu, Deliang Guo, Hiromasa Tanaka, Nanping WangChaoshu Tang, Bruce D. Hammock, John Y.-J. Shyy & Yi Zhu. (2007) Angiotensin II up-regulates soluble epoxide hydrolase in vascular endothelium in vitro and in vivo . Proceedings of the National Academy of Sciences 104:21, pages 9018-9023.
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Ann Thomaeus, Jens Carlsson, Johan Åqvist & Mikael Widersten. (2007) Active Site of Epoxide Hydrolases Revisited:  A Noncanonical Residue in Potato StEH1 Promotes both Formation and Breakdown of the Alkylenzyme Intermediate. Biochemistry 46:9, pages 2466-2479.
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Carel A. G. M. Weijers, Paul M. Könst, Maurice C. R. Franssen & Ernst J. R. Sudhölter. (2007) Stereochemical preference of yeast epoxide hydrolase for the O-axial C3 epimers of 1-oxaspiro[2.5]octanes. Organic & Biomolecular Chemistry 5:19, pages 3106.
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Takashi Iyanagi. 2007. 35 112 .
Seungha Hwang, Hyejin Hyun, Byoungju Lee, Youngseub Park, Eun Yeol Lee & Chayong Choi. (2006) Purification and characterization of a recombinantCaulobacter crescentus epoxide hydrolase. Biotechnology and Bioprocess Engineering 11:4, pages 282-287.
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Andrew R. Gallimore, Christian B.W. Stark, Apoorva Bhatt, Barbara M. Harvey, Yuliya Demydchuk, Victor Bolanos-Garcia, Daniel J. Fowler, James Staunton, Peter F. Leadlay & Jonathan B. Spencer. (2006) Evidence for the Role of the monB Genes in Polyether Ring Formation during Monensin Biosynthesis. Chemistry & Biology 13:4, pages 453-460.
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T.R. Harris, C. Morisseau, R.L. Walzem, S.J. Ma & B.D. Hammock. (2006) The Cloning and Characterization of a Soluble Epoxide Hydrolase in Chicken. Poultry Science 85:2, pages 278-287.
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Christophe MorisseauBruce D. Hammock. (2005) EPOXIDE HYDROLASES: Mechanisms, Inhibitor Designs, and Biological Roles. Annual Review of Pharmacology and Toxicology 45:1, pages 311-333.
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Carel A. G. M. Weijers, Petra Meeuwse, Robert L. J. M. Herpers, Maurice C. R. Franssen & Ernst J. R. Sudhölter. (2005) Stereoselectivity and Substrate Specificity in the Kinetic Resolution of Methyl-Substituted 1-Oxaspiro[2.5]octanes by Rhodotorula g lutinis Epoxide Hydrolase . The Journal of Organic Chemistry 70:17, pages 6639-6646.
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Michael J. Blake, Lisa Castro, J. Steven Leeder & Gregory L. Kearns. (2005) Ontogeny of drug metabolizing enzymes in the neonate. Seminars in Fetal and Neonatal Medicine 10:2, pages 123-138.
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John W. Newman, Christophe Morisseau & Bruce D. Hammock. (2005) Epoxide hydrolases: their roles and interactions with lipid metabolism. Progress in Lipid Research 44:1, pages 1-51.
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Michael Arand, Annette Cronin, Magdalena Adamska & Franz Oesch. 2005. Phase II Conjugation Enzymes and Transport Systems. Phase II Conjugation Enzymes and Transport Systems 569 588 .

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