Epoxide hydrolase and its application in organic synthesis

Organic chemists have become interested in enzymes as catalysts due to their high efficiencies and specificities. Moreover, recent progress in molecular biology and enzyme-related research areas enabled and simplified the production and purification of recombinant enzymes in large quantities and their engineering towards tailor-made biocatalysts using straightforward mutagenesis and screening techniques. This is also true for epoxide hydrolases (EHs), as evidenced by the many published research papers about the synthetic applications of naturally occurring or engineered EHs.

[1]  T. Sugai,et al.  Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide , 2007 .

[2]  B. Witholt,et al.  Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200 , 2006 .

[3]  Wilfred Chen,et al.  Protein Engineering of Epoxide Hydrolase from Agrobacterium radiobacter AD1 for Enhanced Activity and Enantioselective Production of (R)-1-Phenylethane-1,2-Diol , 2005, Applied and Environmental Microbiology.

[4]  P. Kyslík,et al.  Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives. , 2005, Journal of biotechnology.

[5]  Jungbae Kim,et al.  Enhanced stability and reusability of marine epoxide hydrolase using ship-in-a-bottle approach with magnetically-separable mesoporous silica , 2013 .

[6]  Dick B. Janssen,et al.  Biocatalytic Potential of the Epoxide Hydrolase from Agrobacterium radiobacter AD1 and a Mutant with Enhanced Enantioselectivity , 2002 .

[7]  K. Faber,et al.  Chemoenzymatic asymmetric total syntheses of a constituent of Jamaican rum and of (+)-Pestalotin using an enantioconvergent enzyme-triggered cascade reaction , 2002 .

[8]  R. Furstoss,et al.  Microbiological transformations. 27. The first examples for preparative-scale enantioselective or diastereoselective epoxide hydrolyses using microorganisms. An unequivocal access to all four bisabolol stereoisomers , 1993 .

[9]  S. Karboune,et al.  Free and immobilized Aspergillus niger epoxide hydrolase-catalyzed hydrolytic kinetic resolution of racemic p-chlorostyrene oxide in a neat organic solvent medium , 2010 .

[10]  Richard M. Kellogg,et al.  Mutation of Tyrosine Residues Involved in the Alkylation Half Reaction of Epoxide Hydrolase from Agrobacterium radiobacter AD1 Results in Improved Enantioselectivity , 1999 .

[11]  J. Breytenbach,et al.  Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans-1-phenylpropene oxide and (2,3-epoxypropyl)benzene by yeast epoxide hydrolase , 2004, Biotechnology Letters.

[12]  R. Furstoss,et al.  Enzymatic Transformations 63. High‐Concentration Two Liquid‐Liquid Phase Aspergillus niger Epoxide Hydrolase‐Catalysed Resolution: Application to Trifluoromethyl‐Substituted Aromatic Epoxides , 2007 .

[13]  T. Sugai,et al.  The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol , 2010 .

[14]  R. Furstoss,et al.  Microbiological transformations. Part 39: Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: a theoretical analysis and a new method for its determination , 1998 .

[15]  A. Petri,et al.  Efficient immobilization of epoxide hydrolase onto silica gel and use in the enantioselective hydrolysis of racemic para-nitrostyrene oxide , 2005 .

[16]  E. Lee,et al.  Development and characterization of recombinant whole-cell biocatalysts expressing epoxide hydrolase from Rhodotorula glutinis for enantioselective resolution of racemic epoxides , 2006 .

[17]  J. Albertyn,et al.  Cloning of an epoxide hydrolase‐encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica , 2007, Yeast.

[18]  Jiang Pan,et al.  Biocatalytic resolution of glycidyl aryl ethers by Trichosporon loubierii: cell/substrate ratio influences the optical purity of (R)-epoxides , 2004, Biotechnology Letters.

[19]  Dick B Janssen,et al.  Directed evolution of epoxide hydrolase from A. radiobacter toward higher enantioselectivity by error-prone PCR and DNA shuffling. , 2004, Chemistry & biology.

[20]  K. Faber,et al.  Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure , 2001 .

[21]  Yuguo Zheng,et al.  A novel enantioselective epoxide hydrolase from Agromyces mediolanus ZJB120203: Cloning, characterization and application , 2014 .

[22]  M. Widersten,et al.  Structure-function relationships of epoxide hydrolases and their potential use in biocatalysis. , 2010, Biochimica et biophysica acta.

[23]  G. Oberdorfer,et al.  Epoxide‐Hydrolase‐Initiated Hydrolysis/Rearrangement Cascade of a Methylene‐Interrupted Bis‐Epoxide Yields Chiral THF Moieties without Involvement of a “Cyclase” , 2009, Chembiochem : a European journal of chemical biology.

[24]  C. Choi,et al.  Purification and characterization of a recombinantCaulobacter crescentus epoxide hydrolase , 2006 .

[25]  H. Marešová,et al.  Environmental DNA as a source of a novel epoxide hydrolase reacting with aliphatic terminal epoxides , 2009 .

[26]  Wei Zhao,et al.  Directed evolution of metagenome-derived epoxide hydrolase for improved enantioselectivity and enantioconvergence , 2013 .

[27]  Manfred T Reetz,et al.  Manipulating the Expression Rate and Enantioselectivity of an Epoxide Hydrolase by Using Directed Evolution , 2011, Chembiochem : a European journal of chemical biology.

[28]  R. Furstoss,et al.  Enzymatic transformations. Part 55: Highly productive epoxide hydrolase catalysed resolution of an azole antifungal key synthon , 2004 .

[29]  N. Fadnavis,et al.  Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix , 2008 .

[30]  M. Haddad,et al.  An alternative stereoselective synthesis of trans-(2R,3R)-3-hydroxypipecolic acid , 2001 .

[31]  C. Weijers.  Enantioselective Hydrolysis of Aryl, Alicyclic, and Aliphatic Epoxides by Rhodotorula glutinis. , 1997 .

[32]  Production, enrichment and immobilization of a metagenome-derived epoxide hydrolase , 2011 .

[33]  R. Furstoss,et al.  Enzymatic transformations. Part 58: Enantioconvergent biohydrolysis of styrene oxide derivatives catalysed by the Solanum tuberosum epoxide hydrolase , 2004 .

[34]  M. Zong,et al.  Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide. , 2012, Journal of biotechnology.

[35]  Shuke Wu,et al.  Enantioselective Hydrolysis of Racemic and Meso-Epoxides with Recombinant Escherichia coli Expressing Epoxide Hydrolase from Sphingomonas sp. HXN-200: Preparation of Epoxides and Vicinal Diols in High ee and High Concentration , 2013 .

[36]  Wolfgang Kroutil,et al.  Chemoenzymatic deracemization of (±)-2,2-disubstituted oxiranes , 1998 .

[37]  R. Furstoss,et al.  Microbiological Transformations 43. Epoxide Hydrolases as Tools for the Synthesis of Enantiopure α-Methylstyrene Oxides:  A New and Efficient Synthesis of (S)-Ibuprofen. , 1999, The Journal of organic chemistry.

[38]  Helena Hellström,et al.  Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane: optimization and upscaling , 2001, Biotechnology Letters.

[39]  U. Bornscheuer,et al.  One‐step enzyme extraction and immobilization for biocatalysis applications , 2011, Biotechnology journal.

[40]  Franz Oesch,et al.  Structure of Rhodococcus erythropolis limonene‐1,2‐epoxide hydrolase reveals a novel active site , 2003, The EMBO journal.

[41]  M. Wubbolts,et al.  Diversity and Biocatalytic Potential of Epoxide Hydrolases Identified by Genome Analysis , 2006, Applied and Environmental Microbiology.

[42]  Kurt Faber,et al.  Selectivity enhancement of epoxide hydrolase catalyzed resolution of 2,2-disubstituted oxiranes by substrate modification , 2000 .

[43]  R. Furstoss,et al.  Epoxide Hydrolases and Their Synthetic Applications , 2010 .

[44]  A. Glieder,et al.  Enantioselective trans-Dihydroxylation of Aryl Olefins by Cascade Biocatalysis with Recombinant Escherichia coli Coexpressing Monooxygenase and Epoxide Hydrolase , 2014 .

[45]  A. Archelas,et al.  Microbiological transformations. 30. Enantioselective hydrolysis of racemic epoxides: the synthesis of enantiopure insect juvenile hormone analogs (bower's compound) , 1993 .

[46]  R. Fernández-Lafuente,et al.  Enzymatic transformations. Immobilized A. niger epoxide hydrolase as a novel biocatalytic tool for repeated-batch hydrolytic kinetic resolution of epoxides. , 2003, Organic & biomolecular chemistry.

[47]  Thierry Hotelier,et al.  ESTHER, the database of the α/β-hydrolase fold superfamily of proteins: tools to explore diversity of functions , 2012, Nucleic Acids Res..

[48]  J. Kingma,et al.  Tyrosine residues serve as proton donor in the catalytic mechanism of epoxide hydrolase from Agrobacterium radiobacter. , 2000, Biochemistry.

[49]  R. Sheldon.  Cross-linked enzyme aggregates (CLEA , 2007 .

[50]  R. Furstoss,et al.  Microbiological transformations 40. Use of fungal epoxide hydrolases for the synthesis of enantiopure alkyl epoxides , 1998 .

[51]  Manfred T Reetz,et al.  Directed evolution of enantioselective enzymes: iterative cycles of CASTing for probing protein-sequence space. , 2006, Angewandte Chemie.

[52]  B. Shen,et al.  Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster. , 2010, Organic letters.

[53]  C. Morisseau,et al.  Microbiological transformations 37. An enantioconvergent synthesis of the β-blocker (R)-Nifénalol® using a combined chemoenzymatic approach , 1997 .

[54]  V. Soloshonok.  Enantiocontrolled synthesis of fluoro-organic compounds : stereochemical challenges and biomedical targets , 1999 .

[55]  E. Sudhölter,et al.  Stereoselectivity and substrate specificity in the kinetic resolution of methyl-substituted 1-oxaspiro[2.5]octanes by Rhodotorula glutinis epoxide hydrolase. , 2005, Journal of Organic Chemistry.

[56]  B. Hammock,et al.  Effect of ionic liquids on epoxide hydrolase-catalyzed synthesis of chiral 1,2-diols. , 2007, Green chemistry : an international journal and green chemistry resource : GC.

[57]  Preparation of (R)- and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio- and stereoselective, and easy to handle biocatalyst. , 2001, The Journal of organic chemistry.

[58]  Kurt Faber,et al.  Enantiocomplementary Chemoenzymatic Asymmetric Synthesis of (R)‐ and (S)‐Chromanemethanol , 2009 .

[59]  R. Furstoss,et al.  Microbiological transformations. 28. Enantiocomplementary epoxide hydrolyses as a preparative access to both enantiomers of styrene oxide , 1993 .

[60]  Manfred T Reetz,et al.  Directed evolution of an enantioselective epoxide hydrolase: uncovering the source of enantioselectivity at each evolutionary stage. , 2009, Journal of the American Chemical Society.

[61]  Yu-Guo Zheng,et al.  Biosynthesis of (R)‐epichlorohydrin at high substrate concentration by kinetic resolution of racemic epichlorohydrin with a recombinant epoxide hydrolase , 2013 .

[62]  A. Liese,et al.  Construction and Characterisation of a Genetically Engineered Escherichia coli Strain for the Epoxide Hydrolase-catalysed Kinetic Resolution of Epoxides , 2003 .

[63]  Roland Wohlgemuth,et al.  Influence of pH on the expression of a recombinant epoxide hydrolase in Aspergillus niger. , 2009, Biotechnology journal.

[64]  M. Chartrain,et al.  Chiral Bio-Resolution of Racemic Indene oxide by Fungal Epoxide Hydrolases , 1995 .

[65]  Pavel Kyslík,et al.  Purification and characterisation of a novel enantioselective epoxide hydrolase from Aspergillus niger M200. , 2006, Biochimica et biophysica acta.

[66]  H. Krieg,et al.  Calcium alginate entrapment of the yeast Rhodosporidium toruloides for the kinetic resolution of 1,2-epoxyoctane , 2003, Biotechnology Letters.

[67]  A. Goldman,et al.  Of barn owls and bankers: a lush variety of α/β hydrolases , 1999 .

[68]  Q. Broxterman,et al.  Microbiological transformations 50: selection of epoxide hydrolases for enzymatic resolution of 2-, 3- or 4-pyridyloxirane , 2002 .

[69]  Wilfred Chen,et al.  Enantioconvergent production of (R)‐1‐phenyl‐1,2‐ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases , 2006, Biotechnology and bioengineering.

[70]  Wolfgang Kroutil,et al.  CHEMOENZYMATIC SYNTHESIS OF (S)-(-)-FRONTALIN USING BACTERIAL EPOXIDE HYDROLASES , 1997 .

[71]  M. Arand,et al.  Mammalian epoxide hydrolases in xenobiotic metabolism and signalling , 2009, Archives of Toxicology.

[72]  L. Elfström,et al.  The Saccharomyces cerevisiae ORF YNR064c protein has characteristics of an 'orphaned' epoxide hydrolase. , 2005, Biochimica et biophysica acta.

[73]  W. Kroutil,et al.  Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: kinetics of an enantioconvergent process , 1997 .

[74]  T. Sugai,et al.  Chemoenzymatic approach to enantiomerically pure (R)-3-Hydroxy-3-methyl-4- pentenoic acid ester and its application to a formal total synthesis of taurospongin A , 2008 .

[75]  C. Morisseau,et al.  Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger , 1997 .

[76]  A. Mildvan.  Inverse thinking about double mutants of enzymes. , 2004, Biochemistry.

[77]  In Su Lee,et al.  Functional expression and magnetic nanoparticle-based Immobilization of a protein-engineered marine fish epoxide hydrolase of Mugil cephalus for enantioselective hydrolysis of racemic styrene oxide , 2010, Biotechnology Letters.

[78]  Alain Archelas,et al.  Properties of epoxide hydrolase from Aspergillus niger for the hydrolytic kinetic resolution of epoxides in pure organic media , 2006 .

[79]  C. Weijers,et al.  Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities , 1998, Biotechnology Letters.

[80]  T. Bergfors,et al.  Structure of an atypical epoxide hydrolase from Mycobacterium tuberculosis gives insights into its function. , 2005, Journal of molecular biology.

[81]  B. Hammock,et al.  Biocatalysis in ionic liquids: the stereoconvergent hydrolysis of trans-β-methylstyrene oxide catalyzed by soluble epoxide hydrolase , 2004 .

[82]  In Su Lee,et al.  Synthesis of hybrid Fe(3)O(4)-silica-NiO superstructures and their application as magnetically separable high-performance biocatalysts. , 2009, Chemical communications.

[83]  D. Yıldırım,et al.  Immobilized Aspergillus niger epoxide hydrolases: Cost-effective biocatalysts for the prepation of enantiopure styrene oxide, propylene oxide and epichlorohydrin , 2013 .

[84]  W. Kroutil,et al.  Biocatalytic Resolution of 2-Methyl-2-(aryl)alkyloxiranes Using Novel Bacterial Epoxide Hydrolases. , 1997 .

[85]  Yosephine Gumulya,et al.  Iterative saturation mutagenesis accelerates laboratory evolution of enzyme stereoselectivity: rigorous comparison with traditional methods. , 2010, Journal of the American Chemical Society.

[86]  B. Witholt,et al.  Preparation of (R)- and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio- and stereoselective, and easy to handle biocatalyst. , 2001, The Journal of organic chemistry.

[87]  O. Calvez,et al.  Enantioselective synthesis of 2,3-disubstituted piperidines from (S)-methylpyroglutamate , 1998 .

[88]  Sze Min Puah,et al.  Production of (R)-ethyl-3,4-epoxybutyrate by newly isolated Acinetobacter baumannii containing epoxide hydrolase , 2008, Applied Microbiology and Biotechnology.

[89]  C. Choi,et al.  One-pot biotransformation of racemic styrene oxide into (R)-1,2-phenylethandiol by two recombinant microbial epoxide hydrolases , 2008 .

[90]  M. V. Dyk,et al.  Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides , 1999 .

[91]  R. Furstoss,et al.  Enzymatic Transformations 62. Preparative Scale Synthesis of Enantiopure Glycidyl Acetals using an Aspergillus niger Epoxide Hydrolase-Catalysed Kinetic Resolution , 2006 .

[92]  C. Morisseau.  Role of epoxide hydrolases in lipid metabolism. , 2013, Biochimie.

[93]  B. Hammock,et al.  Epoxide hydrolases: their roles and interactions with lipid metabolism. , 2005, Progress in lipid research.

[94]  M. Zong,et al.  Efficient asymmetric hydrolysis of styrene oxide catalyzed by Mung bean epoxide hydrolases in ionic liquid-based biphasic systems. , 2012, Bioresource technology.

[95]  R. Furstoss,et al.  Epoxide Hydrolase‐Catalysed Kinetic Resolution of a Spiroepoxide, a Key Building Block of Various 11‐Heterosteroids , 2007 .

[96]  S. Karboune,et al.  Immobilization of the Solanum tuberosum epoxide hydrolase and its application in an enantioconvergent process , 2005 .

[97]  Yun Tang,et al.  An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers , 2011 .

[98]  Eun Yeol Lee,et al.  Enantioselective resolution of racemic styrene oxide at high concentration using recombinant Pichia pastoris expressing epoxide hydrolase of Rhodotorula glutinis in the presence of surfactant and glycerol , 2008, Biotechnology Letters.

[99]  Huabao Zheng,et al.  Directed Evolution of Enantioconvergency: The Case of an Epoxide Hydrolase‐Catalyzed Reaction of a Racemic Epoxide , 2010 .

[100]  C. Choi,et al.  Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus , 2008, Biotechnology Letters.

[101]  L. Hecquet,et al.  Transketolase-Mediated Synthesis of 4-Deoxy-d-fructose 6-Phosphate by Epoxide Hydrolase-Catalysed Resolution of 1,1-Diethoxy-3,4-epoxybutane , 1999 .

[102]  Manfred T Reetz,et al.  Manipulating the stereoselectivity of limonene epoxide hydrolase by directed evolution based on iterative saturation mutagenesis. , 2010, Journal of the American Chemical Society.

[103]  S. Karboune,et al.  Immobilization of epoxide hydrolase from Aspergillus niger onto DEAE-cellulose: enzymatic properties and application for the enantioselective resolution of a racemic epoxide , 2005 .

[104]  L. V. D. van der Ploeg,et al.  Discovery of N-[(1S,2S)-3-(4-Chlorophenyl)-2- (3-cyanophenyl)-1-methylpropyl]-2-methyl-2- {[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. , 2006, Journal of medicinal chemistry.

[105]  B. Witholt,et al.  Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols. , 2003, Chemical communications.

[106]  Günter Helmchen,et al.  Basic Principles of the CIP-System and Proposals for a Revision† , 1982 .

[107]  R. Mitra,et al.  Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology , 2008 .

[108]  Yoshiro Furukawa,et al.  Chiral C3 epoxides and halohydrins: Their preparation and synthetic application , 1998 .

[109]  R. Gentz,et al.  Genetic Approach to Facilitate Purification of Recombinant Proteins with a Novel Metal Chelate Adsorbent , 1988, Bio/Technology.

[110]  Daniel I. C. Wang,et al.  Facile fabrication of recyclable and active nanobiocatalyst: purification and immobilization of enzyme in one pot with Ni-NTA functionalized magnetic nanoparticle. , 2011, Chemical communications.

[111]  K. Faber,et al.  Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether , 2006 .

[112]  R. Fernández-Lafuente,et al.  Preparation of a very stable immobilized Solanum tuberosum epoxide hydrolase , 2007 .

[113]  D. Janssen,et al.  Microbiological transformations. Part 48: Enantioselective biohydrolysis of 2-, 3- and 4-pyridyloxirane at high substrate concentration using the Agrobacterium radiobacter AD1 epoxide hydrolase and its Tyr215Phe mutant , 2001 .

[114]  C. Sih,et al.  Quantitative analyses of biochemical kinetic resolutions of enantiomers , 1982 .

[115]  B. Gogoi,et al.  Enantioconvergent Biohydrolysis of Racemic Styrene Oxide to R-phenyl-1, 2-ethanediol by a Newly Isolated Filamentous Fungus Aspergillus tubingensis TF1 , 2013, Applied Biochemistry and Biotechnology.

[116]  V. Křen,et al.  Laboratory evolution of an epoxide hydrolase - towards an enantioconvergent biocatalyst. , 2011, Journal of biotechnology.

[117]  Michal Grulich,et al.  Access to enantiopure aromatic epoxides and diols using epoxide hydrolases derived from total biofilter DNA , 2010 .

[118]  Yue Feng,et al.  Discovery of N-[(1S,2S)-3-(4-Chlorophenyl)-2- (3-cyanophenyl)-1-methylpropyl]-2-methyl-2- {[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. , 2006, Journal of medicinal chemistry.

[119]  Manfred T Reetz,et al.  Addressing the Numbers Problem in Directed Evolution , 2008, Chembiochem : a European journal of chemical biology.

[120]  K. Faber,et al.  Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction. , 2002, The Journal of organic chemistry.

[121]  C. Morisseau,et al.  Microbiological Transformations. 33. Fungal Epoxide Hydrolases Applied to the Synthesis of Enantiopure Para-Substituted Styrene Oxides. A Mechanistic Approach. , 1996, The Journal of organic chemistry.

[122]  E. Eliel.  The R/S system: A method for assignment and some recent modifications , 1985 .

[123]  D. Leak,et al.  Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2-epoxycyclohexane: the synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol , 1996 .

[124]  M. Bučko,et al.  Immobilization of a whole-cell epoxide-hydrolyzing biocatalyst in sodium alginate−cellulose sulfate−poly(methylene-co-guanidine) capsules using a controlled encapsulation process , 2005 .

[125]  R. Furstoss,et al.  Microbiological transformations. Part 45: A green chemistry preparative scale synthesis of enantiopure building blocks of Eliprodil: elaboration of a high substrate concentration epoxide hydrolase-catalyzed hydrolytic kinetic resolution process , 2001 .

[126]  K. Faber,et al.  Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes , 2001 .

[127]  K. Faber,et al.  Chemo-enzymatic Synthesis of (2R,5S)- and (2R,5R)-5-(1-Hydroxy-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran (‘Linalool Oxide’): Preparative Application of a Highly Selective Bacterial Epoxide Hydrolase , 1996 .

[128]  Jian‐He Xu,et al.  Bio-resolution of a chiral epoxide using whole cells of Bacillus megaterium ECU1001 in a biphasic system , 2005 .

[129]  W. Hinz,et al.  Catalytic triad of microsomal epoxide hydrolase: replacement of Glu404 with Asp leads to a strongly increased turnover rate. , 1999, The Biochemical journal.

[130]  Chiehying Y Chang,et al.  Discovery of a (1H-benzoimidazol-2-yl)-1H-pyridin-2-one (BMS-536924) inhibitor of insulin-like growth factor I receptor kinase with in vivo antitumor activity. , 2005, Journal of medicinal chemistry.

[131]  J. Kingma,et al.  Improved enantioselective conversion of styrene epoxides and meso-epoxides through epoxide hydrolases with a mutated nucleophile-flanking residue , 2009 .

[132]  M. Kotik.  Novel genes retrieved from environmental DNA by polymerase chain reaction: current genome-walking techniques for future metagenome applications. , 2009, Journal of biotechnology.

[133]  Yuguo Zheng,et al.  Production of (R)-epichlorohydrin from 1,3-dichloro-2-propanol by two-step biocatalysis using haloalcohol dehalogenase and epoxide hydrolase in two-phase system , 2013 .

[134]  A. Minami,et al.  Enzymatic epoxide-opening cascades catalyzed by a pair of epoxide hydrolases in the ionophore polyether biosynthesis. , 2011, Organic letters.

[135]  B. Hammock,et al.  Molecular cloning and expression of murine liver soluble epoxide hydrolase. , 1993, The Journal of biological chemistry.