메뉴 건너뛰기




Volumn 84, Issue 2, 2009, Pages 239-247

Biotechnological production of enantiopure epoxides by enzymatic kinetic resolution

Author keywords

Enantiopure epoxides; Enantioselective hydrolysis; Epoxide hydrolase; Kinetic resolution

Indexed keywords

BIOLOGICAL TECHNOLOGY; BIOTECHNOLOGICAL PRODUCTION; ENANTIOPURE; ENANTIOPURE EPOXIDES; ENANTIOPURITY; ENANTIOSELECTIVE HYDROLYSIS; ENZYMATIC KINETIC; EPOXIDE HYDROLASE; EPOXIDE HYDROLASES; FINE CHEMICALS; HIGH ENANTIOSELECTIVITY; HIGH-THROUGHPUT ASSAYS; KINETIC RESOLUTION; MARKET DEMAND; ORGANIC SYNTHESIS; SCALE RESOLUTION; SYNTHONS; TECHNICAL PROGRESS; VICINAL DIOLS;

EID: 68749119358     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2110-9     Document Type: Short Survey
Times cited : (70)

References (78)
  • 1
    • 0000337135 scopus 로고    scopus 로고
    • Biocatalytic approaches for the synthesis of enantiopure epoxides
    • A Archelas R Furstoss 1999 Biocatalytic approaches for the synthesis of enantiopure epoxides Top Curr Chem 200 159 191
    • (1999) Top Curr Chem , vol.200 , pp. 159-191
    • Archelas, A.1    Furstoss, R.2
  • 2
    • 0035313421 scopus 로고    scopus 로고
    • Synthetic applications of epoxide hydrolases
    • A Archelas R Furstoss 2001 Synthetic applications of epoxide hydrolases Curr Opin Chem Biol 5 112 119
    • (2001) Curr Opin Chem Biol , vol.5 , pp. 112-119
    • Archelas, A.1    Furstoss, R.2
  • 4
    • 0035810303 scopus 로고    scopus 로고
    • Effect of mass transfer limitations on the enzymatic kinetic resolution of epoxides in a two-liquid-phase system
    • H Baldascini KJ Ganzeveld DB Janssen AACM Beenackers 2001 Effect of mass transfer limitations on the enzymatic kinetic resolution of epoxides in a two-liquid-phase system Biotechnol Bioeng 73 44 53
    • (2001) Biotechnol Bioeng , vol.73 , pp. 44-53
    • Baldascini, H.1    Ganzeveld, K.J.2    Janssen, D.B.3    Aacm, B.4
  • 5
    • 0027934450 scopus 로고
    • Chemical and biological synthesis of enantiopure epoxides
    • P Besse H Veschambre 1994 Chemical and biological synthesis of enantiopure epoxides Tetrahedron 50 8885 8927
    • (1994) Tetrahedron , vol.50 , pp. 8885-8927
    • Besse, P.1    Veschambre, H.2
  • 6
    • 34547204129 scopus 로고    scopus 로고
    • Epoxide hydrolase-catalysed kinetic resolution of a spiroepoxide, a key building block of various 11-heterosteroids
    • A Bottalla M Ibrahim-Ouali M Santelli R Furstoss A Archelas 2007 Epoxide hydrolase-catalysed kinetic resolution of a spiroepoxide, a key building block of various 11-heterosteroids Adv Synth Catal 349 1102 1110
    • (2007) Adv Synth Catal , vol.349 , pp. 1102-1110
    • Bottalla, A.1    Ibrahim-Ouali, M.2    Santelli, M.3    Furstoss, R.4    Archelas, A.5
  • 7
    • 33745211891 scopus 로고    scopus 로고
    • 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
    • L Cao J Lee JW Chen TK Wood 2006 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 Biotechnol Bioeng 94 522 529
    • (2006) Biotechnol Bioeng , vol.94 , pp. 522-529
    • Cao, L.1    Lee, J.2    Chen, J.W.3    Wood, T.K.4
  • 9
    • 28444455635 scopus 로고    scopus 로고
    • Colorimetric assays for quantitative analysis and screening of epoxide hydrolase activity
    • F Cedrone T Bhatnagar JC Baratti 2005 Colorimetric assays for quantitative analysis and screening of epoxide hydrolase activity Biotechnol Lett 27 1921 1927
    • (2005) Biotechnol Lett , vol.27 , pp. 1921-1927
    • Cedrone, F.1    Bhatnagar, T.2    Baratti, J.C.3
  • 10
    • 21644437031 scopus 로고    scopus 로고
    • Production of chiral epoxides: Epoxide hydrolase-catalyzed enantioselective hydrolysis
    • WJ Choi CY Choi 2005 Production of chiral epoxides: epoxide hydrolase-catalyzed enantioselective hydrolysis Biotechnol Bioprocess Eng 10 167 179
    • (2005) Biotechnol Bioprocess Eng , vol.10 , pp. 167-179
    • Choi, W.J.1    Choi, C.Y.2
  • 11
    • 0033199644 scopus 로고    scopus 로고
    • Biocatalytic production of chiral epichlorohydrin in organic solvent
    • WJ Choi EY Lee SJ Yoon CY Choi 1999 Biocatalytic production of chiral epichlorohydrin in organic solvent J Biosci Bioeng 88 339 341
    • (1999) J Biosci Bioeng , vol.88 , pp. 339-341
    • Choi, W.J.1    Lee, E.Y.2    Yoon, S.J.3    Choi, C.Y.4
  • 12
    • 0033492573 scopus 로고    scopus 로고
    • Resolution of 1, 2-epoxyhexane by Rhodotorula glutinis using a two-phase membrane bioreactor
    • WJ Choi CY Choi JAM de Bont CAGM Weijers 1999 Resolution of 1, 2-epoxyhexane by Rhodotorula glutinis using a two-phase membrane bioreactor Appl Microbiol Biotechnol 53 7 11
    • (1999) Appl Microbiol Biotechnol , vol.53 , pp. 7-11
    • Choi, W.J.1    Choi, C.Y.2    De Bont, J.A.M.3    Cagm, W.4
  • 13
    • 0033678968 scopus 로고    scopus 로고
    • Continuous production of enantiopure 1, 2-epoxyhexane by yeast epoxide hydrolase in a two-phase membrane bioreactor
    • WJ Choi CY Choi JAM de Bont CAGM Weijers 2000 Continuous production of enantiopure 1, 2-epoxyhexane by yeast epoxide hydrolase in a two-phase membrane bioreactor Appl Microbiol Biotechnol 54 641 646
    • (2000) Appl Microbiol Biotechnol , vol.54 , pp. 641-646
    • Choi, W.J.1    Choi, C.Y.2    De Bont, J.A.M.3    Cagm, W.4
  • 14
    • 42149135367 scopus 로고    scopus 로고
    • Production of (R)-ethyl-3, 4-epoxybutyrate by newly isolated Acinetobacter baumannii containing epoxide hydrolase
    • WJ Choi SM Puah LL Tan SS Ng 2008 Production of (R)-ethyl-3, 4-epoxybutyrate by newly isolated Acinetobacter baumannii containing epoxide hydrolase Appl Microbiol Biotechnol 79 61 67
    • (2008) Appl Microbiol Biotechnol , vol.79 , pp. 61-67
    • Choi, W.J.1    Puah, S.M.2    Tan, L.L.3    Ng, S.S.4
  • 15
    • 33746697806 scopus 로고    scopus 로고
    • Enzymatic transformations; 61. Preparation of enantiopure trifluoromethyl-substituted aromatic epoxides and vicinal diols using the Aspergillus niger epoxide hydrolase-catalysed resolution
    • DOI 10.1002/adsc.200606061
    • J Deregnaucourt A Archelas F Barbirato J Paris R Furstoss 2006 Enzymatic transformations; 61. Preparation of enantiopure trifluoromethyl-substituted aromatic epoxides and vicinal diols using the Aspergillus niger epoxide hydrolase-catalysed resolution Adv Synth Catal 348 1165 1169 (Pubitemid 44166100)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.10-11 , pp. 1165-1169
    • Deregnaucourt, J.1    Archelas, A.2    Barbirato, F.3    Paris, J.-M.4    Furstoss, R.5
  • 16
    • 43649097567 scopus 로고    scopus 로고
    • Gelozymes in organic synthesis. part IV: Resolution of glycidate esters with crude mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix
    • AV Devi C Lahari L Swarnalatha NW Fadnavis 2008 Gelozymes in organic synthesis. part IV: resolution of glycidate esters with crude mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix Tetrahedron: Asymmetry 19 1139 1144
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1139-1144
    • Devi, A.V.1    Lahari, C.2    Swarnalatha, L.3    Fadnavis, N.W.4
  • 18
    • 33749356255 scopus 로고    scopus 로고
    • Enzymatic transformations 62. Preparative scale synthesis of enantiopure glycidyl acetals using an Aspergillus niger epoxide hydrolase-catalysed kinetic resolution
    • DOI 10.1002/adsc.200606164
    • B Doumèche A Archelas R Furstoss 2006 Enzymatic transformations 62. Preparative scale synthesis of enantiopure glycidyl acetals using an Aspergillus niger epoxide hydrolase-catalysed kinetic resolution Adv Synth Catal 348 1948 1957 (Pubitemid 44497156)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.14 , pp. 1948-1957
    • Doumeche, B.1    Archelas, A.2    Furstoss, R.3
  • 19
    • 0017859396 scopus 로고
    • Hepatic microsomal epoxide hydrase. Involvement of a histidine at the active site suggests a nucleophilic mechanism
    • GC DuBois E Appella W Levin AYH Lu DM Jerina 1978 Hepatic microsomal epoxide hydrase. Involvement of a histidine at the active site suggests a nucleophilic mechanism J Biol Chem 253 2932 2939
    • (1978) J Biol Chem , vol.253 , pp. 2932-2939
    • Dubois, G.C.1    Appella, E.2    Levin, W.3    Lu, A.Y.H.4    Jerina, D.M.5
  • 20
    • 48849091766 scopus 로고    scopus 로고
    • Formation of enantiopure 5 substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides
    • MM Elenkov L Tang A Meetsma B Hauer DB Janssen 2008 Formation of enantiopure 5 substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides Org Lett 10 2417 2420
    • (2008) Org Lett , vol.10 , pp. 2417-2420
    • Elenkov, M.M.1    Tang, L.2    Meetsma, A.3    Hauer, B.4    Janssen, D.B.5
  • 21
    • 0037155704 scopus 로고    scopus 로고
    • Stereoselectivity in biocatalytic enantioconvergent reactions and a computer program for its determination
    • K Faber W Kroutil 2002 Stereoselectivity in biocatalytic enantioconvergent reactions and a computer program for its determination Tetrahedron: Asymmetry 13 377 382
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 377-382
    • Faber, K.1    Kroutil, W.2
  • 22
    • 50349097477 scopus 로고    scopus 로고
    • Enzyme assay and activity fingerprinting of hydrolases with the red-chromogenic adrenaline test
    • VS Fluxá D Wahler J Reymond 2008 Enzyme assay and activity fingerprinting of hydrolases with the red-chromogenic adrenaline test Nature Protocols 3 1270 1277
    • (2008) Nature Protocols , vol.3 , pp. 1270-1277
    • Fluxá, V.S.1    Wahler, D.2    Reymond, J.3
  • 23
    • 53849148958 scopus 로고    scopus 로고
    • 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
    • A Fujino T Sugai 2008 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 Adv Synth Catal 350 1712 1716
    • (2008) Adv Synth Catal , vol.350 , pp. 1712-1716
    • Fujino, A.1    Sugai, T.2
  • 24
    • 33846173011 scopus 로고    scopus 로고
    • 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
    • A Fujino M Asano H Yamaguchi N Shirasaka A Sakoda M Ikunaka 2007 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 Tetrahedron Lett 48 979 983
    • (2007) Tetrahedron Lett , vol.48 , pp. 979-983
    • Fujino, A.1    Asano, M.2    Yamaguchi, H.3    Shirasaka, N.4    Sakoda, A.5    Ikunaka, M.6
  • 27
    • 46649106555 scopus 로고    scopus 로고
    • Catalytic promiscuity of halohydrin dehalogenase and its application in enantioselective epoxide ring opening
    • G Hasnaoui-Dijoux MM Elenkov JH Lutje Spelberg B Hauer DB Janssen 2008 Catalytic promiscuity of halohydrin dehalogenase and its application in enantioselective epoxide ring opening ChemBioChem 9 1048 1051
    • (2008) ChemBioChem , vol.9 , pp. 1048-1051
    • Hasnaoui-Dijoux, G.1    Elenkov, M.M.2    Lutje Spelberg, J.H.3    Hauer, B.4    Janssen, D.B.5
  • 30
    • 39949084661 scopus 로고    scopus 로고
    • Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200
    • X Jia Z Wang Z Li 2008 Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200 Tetrahedron: Asymmetry 19 407 415
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 407-415
    • Jia, X.1    Wang, Z.2    Li, Z.3
  • 32
    • 13844299135 scopus 로고    scopus 로고
    • Immobilization of epoxide hydrolase from Aspergillus niger onto DEAE-cellulose: Enzymatic properties and application for the enantioselective resolution of a racemic epoxide
    • S Karboune A Archelas R Furstoss J Baratti 2005 Immobilization of epoxide hydrolase from Aspergillus niger onto DEAE-cellulose: enzymatic properties and application for the enantioselective resolution of a racemic epoxide J Mol Catal B: Enzym 32 175 183
    • (2005) J Mol Catal B: Enzym , vol.32 , pp. 175-183
    • Karboune, S.1    Archelas, A.2    Furstoss, R.3    Baratti, J.4
  • 33
    • 27944452636 scopus 로고    scopus 로고
    • Cloning and characterization of a fish microsomal epoxide hydrolase of Danio rerio and application to kinetic resolution of racemic styrene oxide
    • HS Kim SJ Lee EJ Lee JW Hwang S Park SJ Kim EY Lee 2005 Cloning and characterization of a fish microsomal epoxide hydrolase of Danio rerio and application to kinetic resolution of racemic styrene oxide J Mol Catal B: Enzym 37 30 35
    • (2005) J Mol Catal B: Enzym , vol.37 , pp. 30-35
    • Kim, H.S.1    Lee, S.J.2    Lee, E.J.3    Hwang, J.W.4    Park, S.5    Kim, S.J.6    Lee, E.Y.7
  • 34
    • 33746353988 scopus 로고    scopus 로고
    • Enantioselective epoxide hydrolase activity of a newly isolated microorganism, Sphingomonas echinoides EH-983, from seawater
    • HS Kim OK Lee SJ Lee S Hwang SJ Kim S Yang S Park EY Lee 2006 Enantioselective epoxide hydrolase activity of a newly isolated microorganism, Sphingomonas echinoides EH-983, from seawater J Mol Catal B: Enzym 41 130 135
    • (2006) J Mol Catal B: Enzym , vol.41 , pp. 130-135
    • Kim, H.S.1    Lee, O.K.2    Lee, S.J.3    Hwang, S.4    Kim, S.J.5    Yang, S.6    Park, S.7    Lee, E.Y.8
  • 35
    • 33644618258 scopus 로고    scopus 로고
    • Purification and characterisation of a novel enantioselective epoxide hydrolase from Aspergillus niger M200
    • M Kotik P Kyslík 2006 Purification and characterisation of a novel enantioselective epoxide hydrolase from Aspergillus niger M200 Biochim Biophys Acta 1760 245 252
    • (2006) Biochim Biophys Acta , vol.1760 , pp. 245-252
    • Kotik, M.1    Kyslík, P.2
  • 36
    • 27744517396 scopus 로고    scopus 로고
    • Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives
    • M Kotik J Brichac P Kyslík 2005 Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives J Biotechnol 120 364 375
    • (2005) J Biotechnol , vol.120 , pp. 364-375
    • Kotik, M.1    Brichac, J.2    Kyslík, P.3
  • 37
    • 0030580210 scopus 로고    scopus 로고
    • Deracemization of (±)-cis-2, 3-epoxyheptane via enantioconvergent biocatalytic hydrolysis using Nocardia EH1-epoxide hydrolase
    • W Kroutil M Mischitz P Plachota K Faber 1996 Deracemization of (±)-cis-2, 3-epoxyheptane via enantioconvergent biocatalytic hydrolysis using Nocardia EH1-epoxide hydrolase Tetrahedron Lett 46 8379 8382
    • (1996) Tetrahedron Lett , vol.46 , pp. 8379-8382
    • Kroutil, W.1    Mischitz, M.2    Plachota, P.3    Faber, K.4
  • 38
    • 33847256438 scopus 로고    scopus 로고
    • Cloning of an epoxide hydrolase-encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica
    • M Labuschagne J Albertyn 2007 Cloning of an epoxide hydrolase-encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica Yeast 24 69 78
    • (2007) Yeast , vol.24 , pp. 69-78
    • Labuschagne, M.1    Albertyn, J.2
  • 39
    • 0000353408 scopus 로고
    • The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate
    • GM Lacourciere RN Armstrong 1993 The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate J Am Chem Soc 115 10466 10467
    • (1993) J Am Chem Soc , vol.115 , pp. 10466-10467
    • Lacourciere, G.M.1    Armstrong, R.N.2
  • 40
    • 49749121824 scopus 로고    scopus 로고
    • Epoxide hydrolase-mediated enantioconvergent bioconversions to prepare chiral epoxides and alcohols
    • EY Lee 2008 Epoxide hydrolase-mediated enantioconvergent bioconversions to prepare chiral epoxides and alcohols Biotechnol Lett 30 1509 1514
    • (2008) Biotechnol Lett , vol.30 , pp. 1509-1514
    • Lee, E.Y.1
  • 41
    • 34948826046 scopus 로고    scopus 로고
    • Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis
    • EY Lee ML Shuler 2007 Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis Biotechnol Bioeng 98 318 327
    • (2007) Biotechnol Bioeng , vol.98 , pp. 318-327
    • Lee, E.Y.1    Shuler, M.L.2
  • 42
    • 33846152368 scopus 로고    scopus 로고
    • Cloning, expression and enantioselective hydrolytic catalysis of a microsomal epoxide hydrolase from a marine fish, Mugil cephalus
    • SJ Lee HS Kim SJ Kim S Park BJ Kim ML Shuler 2007 Cloning, expression and enantioselective hydrolytic catalysis of a microsomal epoxide hydrolase from a marine fish, Mugil cephalus Biotechnol Lett 29 237 246
    • (2007) Biotechnol Lett , vol.29 , pp. 237-246
    • Lee, S.J.1    Kim, H.S.2    Kim, S.J.3    Park, S.4    Kim, B.J.5    Shuler, M.L.6
  • 43
    • 33644769395 scopus 로고    scopus 로고
    • Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation
    • Y Liu Q Sha S Wu J Wang L Yang W Sun 2006 Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation J Ind Microbiol Biotechnol 33 274 282
    • (2006) J Ind Microbiol Biotechnol , vol.33 , pp. 274-282
    • Liu, Y.1    Sha, Q.2    Wu, S.3    Wang, J.4    Yang, L.5    Sun, W.6
  • 44
    • 30944432748 scopus 로고    scopus 로고
    • Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200
    • Z Liu J Michel Z Wang B Witholt Z Li 2006 Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200 Tetrahedron: Asymmetry 17 47 52
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 47-52
    • Liu, Z.1    Michel, J.2    Wang, Z.3    Witholt, B.4    Li, Z.5
  • 45
    • 33846580455 scopus 로고    scopus 로고
    • Cloning, sequencing, and expression of a novel epoxide hydrolase gene from Rhodococcus opacus in Escherichia coli and characterization of enzyme
    • Z Liu Y Li Y Xu L Ping Y Zheng 2007 Cloning, sequencing, and expression of a novel epoxide hydrolase gene from Rhodococcus opacus in Escherichia coli and characterization of enzyme Appl Microbiol Biotechnol 74 99 106
    • (2007) Appl Microbiol Biotechnol , vol.74 , pp. 99-106
    • Liu, Z.1    Li, Y.2    Xu, Y.3    Ping, L.4    Zheng, Y.5
  • 46
    • 0141841817 scopus 로고    scopus 로고
    • Enzymatic transformations. Immobilized Aspergillus niger epoxide hydrolase as a novel biocatalytic tool for repeated-batch hydrolytic kinetic resolution of epoxides
    • C Mateo AA Archelas R Fernandez-Lafuente JM Guisan R Furstoss 2003 Enzymatic transformations. Immobilized Aspergillus niger epoxide hydrolase as a novel biocatalytic tool for repeated-batch hydrolytic kinetic resolution of epoxides Org Biomol Chem 1 2739 2743
    • (2003) Org Biomol Chem , vol.1 , pp. 2739-2743
    • Mateo, C.1    Archelas, A.A.2    Fernandez-Lafuente, R.3    Guisan, J.M.4    Furstoss, R.5
  • 47
    • 0347595455 scopus 로고    scopus 로고
    • Enzymatic transformations. Part 55: Highly productive epoxide hydrolase catalysed resolution of an azole antifungal key synthon
    • N Monfort A Archelas R Furstoss 2004 Enzymatic transformations. Part 55: highly productive epoxide hydrolase catalysed resolution of an azole antifungal key synthon Tetrahedron 60 601 605
    • (2004) Tetrahedron , vol.60 , pp. 601-605
    • Monfort, N.1    Archelas, A.2    Furstoss, R.3
  • 48
    • 4644259619 scopus 로고    scopus 로고
    • Enzymatic transformation. Part 58: Enantioconvergent biohydrolysis of styrene oxide derivatives catalyzed by the Solanum tuberosum epoxide hydrolase
    • ML Monterde M Lombard A Archelas A Cronin M Arand R Furstoss 2004 Enzymatic transformation. Part 58: enantioconvergent biohydrolysis of styrene oxide derivatives catalyzed by the Solanum tuberosum epoxide hydrolase Tetrahedron: Asymmetry 15 2801 2805
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2801-2805
    • Monterde, M.L.1    Lombard, M.2    Archelas, A.3    Cronin, A.4    Arand, M.5    Furstoss, R.6
  • 49
    • 0031149795 scopus 로고    scopus 로고
    • Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger
    • C Morisseau H Nellaiah A Archelas R Furstoss JC Baratti 1997 Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger Enzyme Microb Technol 20 446 452
    • (1997) Enzyme Microb Technol , vol.20 , pp. 446-452
    • Morisseau, C.1    Nellaiah, H.2    Archelas, A.3    Furstoss, R.4    Baratti, J.C.5
  • 50
    • 0000451772 scopus 로고    scopus 로고
    • Microbiological transformations. 38. Clues to the involvement of a general acid activation during hydrolysis of para-substituted styrene oxides by a soluble epoxide hydrolase from Syncephalastrum racemosum
    • P Moussou A Archelas J Baratti R Furstoss 1998 Microbiological transformations. 38. Clues to the involvement of a general acid activation during hydrolysis of para-substituted styrene oxides by a soluble epoxide hydrolase from Syncephalastrum racemosum J Org Chem 63 3532 3537
    • (1998) J Org Chem , vol.63 , pp. 3532-3537
    • Moussou, P.1    Archelas, A.2    Baratti, J.3    Furstoss, R.4
  • 52
    • 0029856005 scopus 로고    scopus 로고
    • Microbiological transformations. 33. Fungal epoxide hydrolases applied to the synthesis of enantiopure para-substituted styrene oxides. A mechanistic approach
    • S Pedragosa-Moreau C Morisseau J Zylber A Archelas J Baratti R Furstoss 1996 Microbiological transformations. 33. Fungal epoxide hydrolases applied to the synthesis of enantiopure para-substituted styrene oxides. A mechanistic approach J Org Chem 61 7402 7407
    • (1996) J Org Chem , vol.61 , pp. 7402-7407
    • Pedragosa-Moreau, S.1    Morisseau, C.2    Zylber, J.3    Archelas, A.4    Baratti, J.5    Furstoss, R.6
  • 53
    • 13844296705 scopus 로고    scopus 로고
    • Efficient immobilization of epoxide hydrolase onto silica gel and use in the enantioselective hydrolysis of racemic para-nitrostyrene oxide
    • A Petri P Marconcini P Salvadori 2005 Efficient immobilization of epoxide hydrolase onto silica gel and use in the enantioselective hydrolysis of racemic para-nitrostyrene oxide J Mol Catal B: Enzym 32 219 224
    • (2005) J Mol Catal B: Enzym , vol.32 , pp. 219-224
    • Petri, A.1    Marconcini, P.2    Salvadori, P.3
  • 54
    • 53549084042 scopus 로고    scopus 로고
    • Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology
    • DP Pienaar RK Mitra TI Deventer AL Botes 2008 Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology Tetrahedron Lett 49 6752 6755
    • (2008) Tetrahedron Lett , vol.49 , pp. 6752-6755
    • Pienaar, D.P.1    Mitra, R.K.2    Deventer, T.I.3    Botes, A.L.4
  • 55
    • 33646473069 scopus 로고    scopus 로고
    • Directed evolution of enantioselective enzymes as catalysts for organic synthesis
    • MT Reetz 2006 Directed evolution of enantioselective enzymes as catalysts for organic synthesis Adv Catal 49 1 69
    • (2006) Adv Catal , vol.49 , pp. 1-69
    • Reetz, M.T.1
  • 56
    • 33744473320 scopus 로고    scopus 로고
    • High-throughput selection system for assessing the activity of epoxide hydrolases
    • MT Reetz L Wang 2006 High-throughput selection system for assessing the activity of epoxide hydrolases Comb Chem High Throughput Screen 9 295 299
    • (2006) Comb Chem High Throughput Screen , vol.9 , pp. 295-299
    • Reetz, M.T.1    Wang, L.2
  • 58
    • 33744475011 scopus 로고    scopus 로고
    • Directed evolution of enantioselective enzymes: Iterative cycles of CASTing for probing protein-sequence space
    • MT Reetz L Wang M Bocola 2006 Directed evolution of enantioselective enzymes: iterative cycles of CASTing for probing protein-sequence space Angew Chem Int Ed 45 1236 1241
    • (2006) Angew Chem Int Ed , vol.45 , pp. 1236-1241
    • Reetz, M.T.1    Wang, L.2    Bocola, M.3
  • 59
    • 0032558964 scopus 로고    scopus 로고
    • Kinetic mechanism of the enantioselective conversion of styrene oxide by epoxide hydrolase from Agrobacterium radiobacter AD1
    • R Rink DB Janssen 1998 Kinetic mechanism of the enantioselective conversion of styrene oxide by epoxide hydrolase from Agrobacterium radiobacter AD1 Biochemistry 37 18119 18127
    • (1998) Biochemistry , vol.37 , pp. 18119-18127
    • Rink, R.1    Janssen, D.B.2
  • 60
    • 0345624451 scopus 로고    scopus 로고
    • Mutation of tyrosine residues involved in the alkylation half reaction of epoxide hydrolase from Agrobacterium radiobacter AD1 results in improved enantioselectivity
    • R Rink JHL Spelberg RJ Pieters J Kingma M Nardini RM Kellogg BW Dijkstra DB Janssen 1999 Mutation of tyrosine residues involved in the alkylation half reaction of epoxide hydrolase from Agrobacterium radiobacter AD1 results in improved enantioselectivity J Am Chem Soc 121 7417 7418
    • (1999) J Am Chem Soc , vol.121 , pp. 7417-7418
    • Rink, R.1    Spelberg, J.H.L.2    Pieters, R.J.3    Kingma, J.4    Nardini, M.5    Kellogg, R.M.6    Dijkstra, B.W.7    Janssen, D.B.8
  • 61
    • 22144457118 scopus 로고    scopus 로고
    • Protein engineering of epoxide hydrolase from Agrobacterium radiobacter AD1 for enhanced activity and enantioselective production of (R)-1-phenylethane-1, 2-diol
    • L Rui L Cao W Chen KF Reardon TK Wood 2005 Protein engineering of epoxide hydrolase from Agrobacterium radiobacter AD1 for enhanced activity and enantioselective production of (R)-1-phenylethane-1, 2-diol Appl Environ Microbiol 71 3995 4003
    • (2005) Appl Environ Microbiol , vol.71 , pp. 3995-4003
    • Rui, L.1    Cao, L.2    Chen, W.3    Reardon, K.F.4    Wood, T.K.5
  • 62
    • 0036037970 scopus 로고    scopus 로고
    • Second-generation MS based high-throughput screening system for enantioselective catalysis and biocatalysis
    • W Schrader A Eipper DJ Pugh MT Reetz 2002 Second-generation MS based high-throughput screening system for enantioselective catalysis and biocatalysis Can J Chem 80 626 632
    • (2002) Can J Chem , vol.80 , pp. 626-632
    • Schrader, W.1    Eipper, A.2    Pugh, D.J.3    Reetz, M.T.4
  • 63
    • 33644695706 scopus 로고    scopus 로고
    • Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether
    • Y Simeó K Faber 2006 Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether Tetrahedron: Asymmetry 17 402 409
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 402-409
    • Simeó, Y.1    Faber, K.2
  • 64
    • 85037455306 scopus 로고
    • Synthetically useful reactions of epoxides
    • Smith JG (1984) Synthetically useful reactions of epoxides. Synthesis 629-656
    • (1984) Synthesis , pp. 629-656
    • Smith, J.G.1
  • 65
    • 0035710814 scopus 로고    scopus 로고
    • Microbial epoxide hydrolases for preparative biotransformations
    • A Steinreiber K Faber 2001 Microbial epoxide hydrolases for preparative biotransformations Curr Opin Biotechnol 12 552 558
    • (2001) Curr Opin Biotechnol , vol.12 , pp. 552-558
    • Steinreiber, A.1    Faber, K.2
  • 66
    • 0025652799 scopus 로고
    • Microbial transformation processes of aliphatic-hydrocarbons
    • M Takagi N Uemura K Furuhashi 1990 Microbial transformation processes of aliphatic-hydrocarbons Ann N Y Acad Sci 613 697 701
    • (1990) Ann N y Acad Sci , vol.613 , pp. 697-701
    • Takagi, M.1    Uemura, N.2    Furuhashi, K.3
  • 67
    • 0030860279 scopus 로고    scopus 로고
    • Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis
    • M Tokunaga JF Larrow F Kakiuchi EN Jacobsen 1997 Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis Science 277 936 938
    • (1997) Science , vol.277 , pp. 936-938
    • Tokunaga, M.1    Larrow, J.F.2    Kakiuchi, F.3    Jacobsen, E.N.4
  • 69
    • 3342911436 scopus 로고    scopus 로고
    • Directed evolution of epoxide hydrolase from A. radiobacter toward higher enantioselectivity by error-prone PCR and DNA shuffling
    • B van Loo JHL Spelberg J Kingma T Sonke MG Wubbolts DB Janssen 2004 Directed evolution of epoxide hydrolase from A. radiobacter toward higher enantioselectivity by error-prone PCR and DNA shuffling Chem Biol 11 981 990
    • (2004) Chem Biol , vol.11 , pp. 981-990
    • Van Loo, B.1    Spelberg, J.H.L.2    Kingma, J.3    Sonke, T.4    Wubbolts, M.G.5    Janssen, D.B.6
  • 70
    • 33646084392 scopus 로고    scopus 로고
    • Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis
    • B van Loo J Kingma M Arand MG Wubbolts DB Janssen 2006 Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis Appl Environ Microbiol 72 2905 2917
    • (2006) Appl Environ Microbiol , vol.72 , pp. 2905-2917
    • Van Loo, B.1    Kingma, J.2    Arand, M.3    Wubbolts, M.G.4    Janssen, D.B.5
  • 71
    • 58149477514 scopus 로고    scopus 로고
    • Improved enantioselective conversion of styrene epoxides and meso-epoxides through epoxide hydrolases with a mutated nucleophile-flanking residue
    • B van Loo J Kingma G Heyman A Wittenaar JHL Spelberg T Sonke DB Janssen 2009 Improved enantioselective conversion of styrene epoxides and meso-epoxides through epoxide hydrolases with a mutated nucleophile-flanking residue Enzyme Microb Technol 44 145 153
    • (2009) Enzyme Microb Technol , vol.44 , pp. 145-153
    • Van Loo, B.1    Kingma, J.2    Heyman, G.3    Wittenaar, A.4    Spelberg, J.H.L.5    Sonke, T.6    Janssen, D.B.7
  • 72
    • 0037006788 scopus 로고    scopus 로고
    • The adrenaline test for enzymes
    • D Wahler JL Reymond 2002 The adrenaline test for enzymes Angew Chem Int Ed 41 1229 1232
    • (2002) Angew Chem Int Ed , vol.41 , pp. 1229-1232
    • Wahler, D.1    Reymond, J.L.2
  • 73
    • 0033545515 scopus 로고    scopus 로고
    • Epoxide hydrolases from yeasts and other sources: Versatile tools in biocatalysis
    • CAGM Weijers JAM de Bont 1999 Epoxide hydrolases from yeasts and other sources: versatile tools in biocatalysis J Mol Catal B: Enzym 6 199 214
    • (1999) J Mol Catal B: Enzym , vol.6 , pp. 199-214
    • Cagm, W.1    De Bont, J.A.M.2
  • 74
    • 23644450223 scopus 로고    scopus 로고
    • Stereoselectivity and substrate specificity in the kinetic resolution of methyl-substituted 1-oxaspiro[2.5]octanes by Rhodotorula glutinis epoxide hydrolase
    • CAGM Weijers P Meeuwse RLJM Herpers MCR Franssen EJR Sudhölter 2005 Stereoselectivity and substrate specificity in the kinetic resolution of methyl-substituted 1-oxaspiro[2.5]octanes by Rhodotorula glutinis epoxide hydrolase J Org Chem 70 6639 6646
    • (2005) J Org Chem , vol.70 , pp. 6639-6646
    • Cagm, W.1    Meeuwse, P.2    Rljm, H.3    Franssen, M.C.R.4    Sudhölter, E.J.R.5
  • 75
    • 34648830233 scopus 로고    scopus 로고
    • A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1, 2-propanediol
    • S Wu J Shen X Zhou J Chen 2007 A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1, 2-propanediol Appl Microbiol Biotechnol 76 1281 1287
    • (2007) Appl Microbiol Biotechnol , vol.76 , pp. 1281-1287
    • Wu, S.1    Shen, J.2    Zhou, X.3    Chen, J.4
  • 76
    • 33646443800 scopus 로고    scopus 로고
    • Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean
    • W Xu JH Xu J Pan O Gu XY Wu 2006 Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean Org Lett 8 1737 1740
    • (2006) Org Lett , vol.8 , pp. 1737-1740
    • Xu, W.1    Xu, J.H.2    Pan, J.3    Gu, O.4    Wu, X.Y.5
  • 77
    • 50249137670 scopus 로고    scopus 로고
    • 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
    • SS Yoo S Park EY Lee 2008 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 Biotechnol Lett 30 1807 1810
    • (2008) Biotechnol Lett , vol.30 , pp. 1807-1810
    • Yoo, S.S.1    Park, S.2    Lee, E.Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.