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Volumn 65, Issue , 2016, Pages 82-89

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

Author keywords

(S) 3 (dimethylamino) 1 (2 thienyl) 1 propanol; Asymmetric synthesis; Carbonyl reductases; Chemoenzymatic; Duloxetine

Indexed keywords

CARBONYL REDUCTASE; DULOXETINE; GLUCOSE DEHYDROGENASE; ALCOHOL DEHYDROGENASE; RECOMBINANT PROTEIN;

EID: 84958161089     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2016.02.002     Document Type: Article
Times cited : (37)

References (56)
  • 1
    • 0036112313 scopus 로고    scopus 로고
    • Duloxetine in the treatment of major depressive disorder: A double-blind clinical trial
    • D.J. Goldstein, C. Mallinckrodt, Y.L. Lu, and M.A. Demitrack Duloxetine in the treatment of major depressive disorder: A double-blind clinical trial J. Clin. Psychiatr. 63 2002 225 231
    • (2002) J. Clin. Psychiatr. , vol.63 , pp. 225-231
    • Goldstein, D.J.1    Mallinckrodt, C.2    Lu, Y.L.3    Demitrack, M.A.4
  • 4
    • 84904736010 scopus 로고    scopus 로고
    • Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach
    • A.D.J. Calow, E. Fernandez, and A. Whiting Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach Org. Biomol. Chem. 12 2014 6121 6127
    • (2014) Org. Biomol. Chem. , vol.12 , pp. 6121-6127
    • Calow, A.D.J.1    Fernandez, E.2    Whiting, A.3
  • 5
    • 84922936782 scopus 로고    scopus 로고
    • Kinetic resolution of (R, S)-2-(2-chloro-1-hydroxyethyl) thiophene via immobilizing lipase from Alcaligenes sp. onto magnetic nanoparticles
    • E.N. Xun, Z. Wang, J.M. Zhao, and J.X. Guo Kinetic resolution of (R, S)-2-(2-chloro-1-hydroxyethyl) thiophene via immobilizing lipase from Alcaligenes sp. onto magnetic nanoparticles J. Chem. Technol. Biotechnol. 90 2015 492 499
    • (2015) J. Chem. Technol. Biotechnol. , vol.90 , pp. 492-499
    • Xun, E.N.1    Wang, Z.2    Zhao, J.M.3    Guo, J.X.4
  • 6
    • 84883452986 scopus 로고    scopus 로고
    • Chemoenzymatic asymmetric synthesis of fluoxetine, atomoxetine, nisoxetine, and duloxetine
    • R.K. Rej, T. Das, S. Hazra, and S. Nanda Chemoenzymatic asymmetric synthesis of fluoxetine, atomoxetine, nisoxetine, and duloxetine Tetrahedron-Asymmetry 24 2013 913 918
    • (2013) Tetrahedron-Asymmetry , vol.24 , pp. 913-918
    • Rej, R.K.1    Das, T.2    Hazra, S.3    Nanda, S.4
  • 7
    • 84875701703 scopus 로고    scopus 로고
    • Biocatalytic synthesis of enantiopure building blocks for pharmaceuticals
    • R.C. Simon, F.G. Mutti, and W. Kroutil Biocatalytic synthesis of enantiopure building blocks for pharmaceuticals Drug Discov. Today Technol. 10 2013 e37 e44
    • (2013) Drug Discov. Today Technol. , vol.10 , pp. e37-e44
    • Simon, R.C.1    Mutti, F.G.2    Kroutil, W.3
  • 8
    • 84893901118 scopus 로고    scopus 로고
    • Enantioselective allylation of thiophene-2-carbaldehyde: Formal total synthesis of duloxetine
    • P. Motloch, I. Valterova, and M. Kotora Enantioselective allylation of thiophene-2-carbaldehyde: Formal total synthesis of duloxetine Adv. Synth. Catal. 356 2014 199 204
    • (2014) Adv. Synth. Catal. , vol.356 , pp. 199-204
    • Motloch, P.1    Valterova, I.2    Kotora, M.3
  • 9
    • 0038544136 scopus 로고    scopus 로고
    • Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid
    • K. Sakai, R. Sakurai, A. Yuzawa, Y. Kobayashi, and K. Saigo Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid Tetrahedron-Asymmetry 14 2003 1631 1636
    • (2003) Tetrahedron-Asymmetry , vol.14 , pp. 1631-1636
    • Sakai, K.1    Sakurai, R.2    Yuzawa, A.3    Kobayashi, Y.4    Saigo, K.5
  • 10
    • 70349898271 scopus 로고    scopus 로고
    • Highly enantioselective Friedel-crafts reaction of thiophenes with glyoxylates: Formal synthesis of duloxetine
    • J. Majer, P. Kwiatkowski, and J. Jurczak Highly enantioselective Friedel-crafts reaction of thiophenes with glyoxylates: Formal synthesis of duloxetine Org. Lett. 11 2009 4636 4639
    • (2009) Org. Lett. , vol.11 , pp. 4636-4639
    • Majer, J.1    Kwiatkowski, P.2    Jurczak, J.3
  • 11
    • 84887419508 scopus 로고    scopus 로고
    • Organocatalytic enantioselective decarboxylative aldol reaction of malonic acid half thioesters with aldehydes
    • H.Y. Bae, J.H. Sim, J.W. Lee, B. List, and C.E. Song Organocatalytic enantioselective decarboxylative aldol reaction of malonic acid half thioesters with aldehydes Angew. Chem. Int. Ed. 52 2013 12143 12147
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 12143-12147
    • Bae, H.Y.1    Sim, J.H.2    Lee, J.W.3    List, B.4    Song, C.E.5
  • 12
    • 84860612558 scopus 로고    scopus 로고
    • Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide
    • Y. Suzuki, M. Iwata, R. Yazaki, N. Kumagai, and M. Shibasaki Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide J. Org. Chem. 77 2012 4496 4500
    • (2012) J. Org. Chem. , vol.77 , pp. 4496-4500
    • Suzuki, Y.1    Iwata, M.2    Yazaki, R.3    Kumagai, N.4    Shibasaki, M.5
  • 13
    • 0033982110 scopus 로고    scopus 로고
    • Chemo-enzymatic synthesis of the antidepressant duloxetine and its enantiomer
    • H.L. Liu, B.H. Hoff, and T. Anthonsen Chemo-enzymatic synthesis of the antidepressant duloxetine and its enantiomer Chirality 12 2000 26 29
    • (2000) Chirality , vol.12 , pp. 26-29
    • Liu, H.L.1    Hoff, B.H.2    Anthonsen, T.3
  • 14
    • 0038443005 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of duloxetine and its enantiomer: Lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile
    • A. Kamal, G.B.R. Khanna, R. Ramu, and T. Krishnaji Chemoenzymatic synthesis of duloxetine and its enantiomer: Lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile Tetrahedron Lett. 44 2003 4783 4787
    • (2003) Tetrahedron Lett. , vol.44 , pp. 4783-4787
    • Kamal, A.1    Khanna, G.B.R.2    Ramu, R.3    Krishnaji, T.4
  • 15
    • 63249107465 scopus 로고    scopus 로고
    • Lipase mediated resolution of gamma-azidoalcohols in aqueous and organic media: Synthesis of (R)- and (S)-fluoxetine and duloxetine
    • A. Kamal, M.S. Malik, A.A. Shaik, and S. Azeeza Lipase mediated resolution of gamma-azidoalcohols in aqueous and organic media: Synthesis of (R)- and (S)-fluoxetine and duloxetine J. Mol. Catal. B - Enzym. 58 2009 132 137
    • (2009) J. Mol. Catal. B - Enzym. , vol.58 , pp. 132-137
    • Kamal, A.1    Malik, M.S.2    Shaik, A.A.3    Azeeza, S.4
  • 17
    • 33750136529 scopus 로고    scopus 로고
    • Synthesis of (S)-3-(N-methylamino)-1-(2-thienyl)propan-1-ol: Revisiting Eli Lilly's resolution-racemization-recycle synthesis of duloxetine for its robust processes
    • Y. Fujima, M. Ikunaka, T. Inoue, and J. Matsumoto Synthesis of (S)-3-(N-methylamino)-1-(2-thienyl)propan-1-ol: Revisiting Eli Lilly's resolution-racemization-recycle synthesis of duloxetine for its robust processes Org. Process Res. Dev. 10 2006 905 913
    • (2006) Org. Process Res. Dev. , vol.10 , pp. 905-913
    • Fujima, Y.1    Ikunaka, M.2    Inoue, T.3    Matsumoto, J.4
  • 18
    • 84909944154 scopus 로고    scopus 로고
    • Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation
    • X. Chen, Y.G. Zheng, Z.Q. Liu, and L.H. Sun Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation J. Chromatogr. B 974 2015 57 64
    • (2015) J. Chromatogr. B , vol.974 , pp. 57-64
    • Chen, X.1    Zheng, Y.G.2    Liu, Z.Q.3    Sun, L.H.4
  • 20
    • 17044381789 scopus 로고    scopus 로고
    • Practical synthesis of enantiopure gamma-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of beta-secondary-amino ketones
    • D. Liu, W.Z. Gao, C.J. Wang, and X.M. Zhang Practical synthesis of enantiopure gamma-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of beta-secondary-amino ketones Angew. Chem. Int. Ed. 44 2005 1687 1689
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1687-1689
    • Liu, D.1    Gao, W.Z.2    Wang, C.J.3    Zhang, X.M.4
  • 21
    • 84870445368 scopus 로고    scopus 로고
    • High throughput screening of a catalyst library for the asymmetric transfer hydrogenation of heteroaromatic ketones: Formal syntheses of (R)-fluoxetine and (S)-duloxetine
    • E. Buitrago, H. Lundberg, H. Andersson, P. Ryberg, and H. Adolfsson High throughput screening of a catalyst library for the asymmetric transfer hydrogenation of heteroaromatic ketones: Formal syntheses of (R)-fluoxetine and (S)-duloxetine ChemCatChem 4 2012 2082 2089
    • (2012) ChemCatChem , vol.4 , pp. 2082-2089
    • Buitrago, E.1    Lundberg, H.2    Andersson, H.3    Ryberg, P.4    Adolfsson, H.5
  • 22
    • 0037556292 scopus 로고    scopus 로고
    • Enantioselective hydrogenation of beta-keto esters using chiral diphosphine-ruthenium complexes: Optimization for academic and industrial purposes and synthetic applications
    • V. Ratovelomanana-Vidal, C. Girard, R. Touati, J.P. Tranchier, B. Ben Hassine, and J.P. Genet Enantioselective hydrogenation of beta-keto esters using chiral diphosphine-ruthenium complexes: Optimization for academic and industrial purposes and synthetic applications Adv. Synth. Catal. 345 2003 261 274
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 261-274
    • Ratovelomanana-Vidal, V.1    Girard, C.2    Touati, R.3    Tranchier, J.P.4    Ben Hassine, B.5    Genet, J.P.6
  • 23
    • 84860178797 scopus 로고    scopus 로고
    • Corey-Itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates
    • R.D. Mahale, S.P. Chaskar, K.E. Patil, G.C. Maikap, and M.K. Gurjar Corey-Itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates Org. Process Res. Dev. 16 2012 710 713
    • (2012) Org. Process Res. Dev. , vol.16 , pp. 710-713
    • Mahale, R.D.1    Chaskar, S.P.2    Patil, K.E.3    Maikap, G.C.4    Gurjar, M.K.5
  • 24
    • 84892573496 scopus 로고    scopus 로고
    • Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: Asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine
    • J.N. Zhou, Q. Fang, Y.H. Hu, L.Y. Yang, F.F. Wu, L.J. Xie, J. Wu, and S.J. Li Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: Asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine Org. Biomol. Chem. 12 2014 1009 1017
    • (2014) Org. Biomol. Chem. , vol.12 , pp. 1009-1017
    • Zhou, J.N.1    Fang, Q.2    Hu, Y.H.3    Yang, L.Y.4    Wu, F.F.5    Xie, L.J.6    Wu, J.7    Li, S.J.8
  • 25
    • 84937232526 scopus 로고    scopus 로고
    • Asymmetric synthesis of optically active methyl-2-benzamido-methyl-3-hydroxy-butyrate by robust short-chain alcohol dehydrogenases from Burkholderia gladioli
    • X. Chen, Z.Q. Liu, J.F. Huang, C.P. Lin, and Y.G. Zheng Asymmetric synthesis of optically active methyl-2-benzamido-methyl-3-hydroxy-butyrate by robust short-chain alcohol dehydrogenases from Burkholderia gladioli Chem. Commun. 51 2015 12328 12331
    • (2015) Chem. Commun. , vol.51 , pp. 12328-12331
    • Chen, X.1    Liu, Z.Q.2    Huang, J.F.3    Lin, C.P.4    Zheng, Y.G.5
  • 26
    • 84902284072 scopus 로고    scopus 로고
    • Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid
    • W.P. Dijkman, D.E. Groothuis, and M.W. Fraaije Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid Angew. Chem. Int. Ed. 53 2014 6515 6518
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 6515-6518
    • Dijkman, W.P.1    Groothuis, D.E.2    Fraaije, M.W.3
  • 27
    • 84896879326 scopus 로고    scopus 로고
    • Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases
    • N. Reinhardt, J. Fischer, R. Coppi, E. Blum, W. Brandt, and B. Drager Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases Bioorg. Chem. 53 2014 37 49
    • (2014) Bioorg. Chem. , vol.53 , pp. 37-49
    • Reinhardt, N.1    Fischer, J.2    Coppi, R.3    Blum, E.4    Brandt, W.5    Drager, B.6
  • 28
    • 84885003040 scopus 로고    scopus 로고
    • Preparation of pharmaceutical important fluorinated 1-arylethanols using isolated enzymes
    • B.H. Hoff, and E. Sundby Preparation of pharmaceutical important fluorinated 1-arylethanols using isolated enzymes Bioorg. Chem. 51 2013 31 47
    • (2013) Bioorg. Chem. , vol.51 , pp. 31-47
    • Hoff, B.H.1    Sundby, E.2
  • 29
    • 84925491463 scopus 로고    scopus 로고
    • Upscale production of ethyl (S)-4-chloro-3-hydroxybutanoate by using carbonyl reductase coupled with glucose dehydrogenase in aqueous-organic solvent system
    • Z.Q. Liu, J.J. Ye, Z.Y. Shen, H.B. Hong, J.B. Yan, Y. Lin, Z.X. Chen, Y.G. Zheng, and Y.C. Shen Upscale production of ethyl (S)-4-chloro-3-hydroxybutanoate by using carbonyl reductase coupled with glucose dehydrogenase in aqueous-organic solvent system Appl. Microbiol. Biotechnol. 99 2015 2119 2129
    • (2015) Appl. Microbiol. Biotechnol. , vol.99 , pp. 2119-2129
    • Liu, Z.Q.1    Ye, J.J.2    Shen, Z.Y.3    Hong, H.B.4    Yan, J.B.5    Lin, Y.6    Chen, Z.X.7    Zheng, Y.G.8    Shen, Y.C.9
  • 30
    • 77951687148 scopus 로고    scopus 로고
    • Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens
    • J.A. Friest, Y. Maezato, S. Broussy, P. Blum, and D.B. Berkowitz Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens J. Am. Chem. Soc. 132 2010 5930 5931
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5930-5931
    • Friest, J.A.1    Maezato, Y.2    Broussy, S.3    Blum, P.4    Berkowitz, D.B.5
  • 31
    • 21344461509 scopus 로고    scopus 로고
    • Biotransformations for the production of the chiral drug (S)-duloxetine catalyzed by a novel isolate of Candida tropicalis
    • P. Soni, and U.C. Banerjee Biotransformations for the production of the chiral drug (S)-duloxetine catalyzed by a novel isolate of Candida tropicalis Appl. Microbiol. Biotechnol. 67 2005 771 777
    • (2005) Appl. Microbiol. Biotechnol. , vol.67 , pp. 771-777
    • Soni, P.1    Banerjee, U.C.2
  • 32
    • 39149137271 scopus 로고    scopus 로고
    • Optimization of process parameters for the production of carbonyl reductase by Candida viswanathii in a laboratory-scale fermentor
    • S. Pankaj, H. Kansal, and U.C. Banerjee Optimization of process parameters for the production of carbonyl reductase by Candida viswanathii in a laboratory-scale fermentor J. Ind. Microbiol. Biotechnol. 35 2008 167 173
    • (2008) J. Ind. Microbiol. Biotechnol. , vol.35 , pp. 167-173
    • Pankaj, S.1    Kansal, H.2    Banerjee, U.C.3
  • 33
    • 84919634945 scopus 로고    scopus 로고
    • Asymmetric synthesis of duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol using immobilized Saccharomyces cerevisiae in liquid-core sodium alginate/chitosan/sodium alginate microcapsules
    • O. Zhimin, Z. Haibing, T. Lan, Z. Wei, and Y. Gensheng Asymmetric synthesis of duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol using immobilized Saccharomyces cerevisiae in liquid-core sodium alginate/chitosan/sodium alginate microcapsules Bioprocess Biosyst. Eng. 37 2014 2243 2250
    • (2014) Bioprocess Biosyst. Eng. , vol.37 , pp. 2243-2250
    • Zhimin, O.1    Haibing, Z.2    Lan, T.3    Wei, Z.4    Gensheng, Y.5
  • 34
    • 84940751259 scopus 로고    scopus 로고
    • Cloning, expression and enzymatic characterization of an aldo-keto reductase from Candida albicans XP1463
    • Y.J. Wang, X.Q. Liu, X. Luo, Z.Q. Liu, and Y.G. Zheng Cloning, expression and enzymatic characterization of an aldo-keto reductase from Candida albicans XP1463 J. Mol. Catal. B - Enzym. 122 2015 44 50
    • (2015) J. Mol. Catal. B - Enzym. , vol.122 , pp. 44-50
    • Wang, Y.J.1    Liu, X.Q.2    Luo, X.3    Liu, Z.Q.4    Zheng, Y.G.5
  • 35
    • 11244302527 scopus 로고    scopus 로고
    • Cloning and overexpression of the Exiguobacterium sp. F42 gene encoding a new short chain dehydrogenase, which catalyzes the stereoselective reduction of ethyl 3-oxo-3-(2-thienyl)propanoate to ethyl (S)-3-hydroxy-3-(2-thienyl)propanoate
    • M. Wada, A. Yoshizumi, Y. Furukawa, H. Kawabata, M. Ueda, H. Takagi, and S. Nakamori Cloning and overexpression of the Exiguobacterium sp. F42 gene encoding a new short chain dehydrogenase, which catalyzes the stereoselective reduction of ethyl 3-oxo-3-(2-thienyl)propanoate to ethyl (S)-3-hydroxy-3-(2-thienyl)propanoate Biosci. Biotechnol. Biochem. 68 2004 1481 1488
    • (2004) Biosci. Biotechnol. Biochem. , vol.68 , pp. 1481-1488
    • Wada, M.1    Yoshizumi, A.2    Furukawa, Y.3    Kawabata, H.4    Ueda, M.5    Takagi, H.6    Nakamori, S.7
  • 36
    • 79958771091 scopus 로고    scopus 로고
    • Highly enantioselective bioreduction of N-methyl-3-oxo-3-(thiophen-2-yl) propanamide for the production of (S)-duloxetine
    • C.G. Tang, H. Lin, C. Zhang, Z.Q. Liu, T. Yang, and Z.L. Wu Highly enantioselective bioreduction of N-methyl-3-oxo-3-(thiophen-2-yl) propanamide for the production of (S)-duloxetine Biotechnol. Lett. 33 2011 1435 1440
    • (2011) Biotechnol. Lett. , vol.33 , pp. 1435-1440
    • Tang, C.G.1    Lin, H.2    Zhang, C.3    Liu, Z.Q.4    Yang, T.5    Wu, Z.L.6
  • 37
    • 84922311674 scopus 로고    scopus 로고
    • Bioreductive production of enantiopure (S)-duloxetine intermediates catalyzed with ketoreductase ChKRED15
    • Z.Q. Ren, Y. Liu, X.Q. Pei, H.B. Wang, and Z.L. Wu Bioreductive production of enantiopure (S)-duloxetine intermediates catalyzed with ketoreductase ChKRED15 J. Mol. Catal. B - Enzym. 113 2015 76 81
    • (2015) J. Mol. Catal. B - Enzym. , vol.113 , pp. 76-81
    • Ren, Z.Q.1    Liu, Y.2    Pei, X.Q.3    Wang, H.B.4    Wu, Z.L.5
  • 40
    • 84879518480 scopus 로고    scopus 로고
    • Screening and improving the recombinant nitrilases and application in biotransformation of iminodiacetonitrile to iminodiacetic acid
    • Z.Q. Liu, P.J. Baker, F. Cheng, Y.P. Xue, Y.G. Zheng, and Y.C. Shen Screening and improving the recombinant nitrilases and application in biotransformation of iminodiacetonitrile to iminodiacetic acid PLoS ONE 8 2013 e67197
    • (2013) PLoS ONE , vol.8 , pp. e67197
    • Liu, Z.Q.1    Baker, P.J.2    Cheng, F.3    Xue, Y.P.4    Zheng, Y.G.5    Shen, Y.C.6
  • 41
    • 84907259449 scopus 로고    scopus 로고
    • Efficient PCR-based amplification of diverse alcohol dehydrogenase genes from metagenomes for improving biocatalysis: Screening of gene-specific amplicons from metagenomes
    • N. Itoh, S. Kariya, and J. Kurokawa Efficient PCR-based amplification of diverse alcohol dehydrogenase genes from metagenomes for improving biocatalysis: Screening of gene-specific amplicons from metagenomes Appl. Environ. Microbiol. 80 2014 6280 6289
    • (2014) Appl. Environ. Microbiol. , vol.80 , pp. 6280-6289
    • Itoh, N.1    Kariya, S.2    Kurokawa, J.3
  • 42
    • 84885903482 scopus 로고    scopus 로고
    • Biochemical and structural characterization of recombinant short-chain NAD(H)-dependent dehydrogenase/reductase from Sulfolobus acidocaldarius highly enantioselective on diaryl diketone benzil
    • A. Pennacchio, V. Sannino, G. Sorrentino, M. Rossi, C.A. Raia, and L. Esposito Biochemical and structural characterization of recombinant short-chain NAD(H)-dependent dehydrogenase/reductase from Sulfolobus acidocaldarius highly enantioselective on diaryl diketone benzil Appl. Microbiol. Biotechnol. 97 2013 3949 3964
    • (2013) Appl. Microbiol. Biotechnol. , vol.97 , pp. 3949-3964
    • Pennacchio, A.1    Sannino, V.2    Sorrentino, G.3    Rossi, M.4    Raia, C.A.5    Esposito, L.6
  • 43
    • 0037459232 scopus 로고    scopus 로고
    • The crystal structure of R-specific alcohol dehydrogenase from Lactobacillus brevis suggests the structural basis of its metal dependency
    • K. Niefind, J. Müller, B. Riebel, W. Hummel, and D. Schomburg The crystal structure of R-specific alcohol dehydrogenase from Lactobacillus brevis suggests the structural basis of its metal dependency J. Mol. Biol. 327 2003 317 328
    • (2003) J. Mol. Biol. , vol.327 , pp. 317-328
    • Niefind, K.1    Müller, J.2    Riebel, B.3    Hummel, W.4    Schomburg, D.5
  • 44
    • 79957851192 scopus 로고    scopus 로고
    • Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor
    • L.J. Wang, C.X. Li, Y. Ni, J. Zhang, X. Liu, and J.H. Xu Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor Bioresour. Technol. 102 2011 7023 7028
    • (2011) Bioresour. Technol. , vol.102 , pp. 7023-7028
    • Wang, L.J.1    Li, C.X.2    Ni, Y.3    Zhang, J.4    Liu, X.5    Xu, J.H.6
  • 45
    • 84894317041 scopus 로고    scopus 로고
    • Characterization of a newly synthesized carbonyl reductase and construction of a biocatalytic process for the synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate with high space-time yield
    • Z.Y. You, Z.Q. Liu, and Y.G. Zheng Characterization of a newly synthesized carbonyl reductase and construction of a biocatalytic process for the synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate with high space-time yield Appl. Microbiol. Biotechnol. 98 2014 1671 1680
    • (2014) Appl. Microbiol. Biotechnol. , vol.98 , pp. 1671-1680
    • You, Z.Y.1    Liu, Z.Q.2    Zheng, Y.G.3
  • 46
    • 43649085325 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure gamma-azidoalcohols by lipase-catalyzed transesterification
    • A. Kamal, M.S. Malik, A.A. Shaik, and S. Azeeza Synthesis of enantiomerically pure gamma-azidoalcohols by lipase-catalyzed transesterification Tetrahedron-Asymmetry 19 2008 1078 1083
    • (2008) Tetrahedron-Asymmetry , vol.19 , pp. 1078-1083
    • Kamal, A.1    Malik, M.S.2    Shaik, A.A.3    Azeeza, S.4
  • 47
    • 17044365321 scopus 로고    scopus 로고
    • Evaluation of substituent effects on activity and enantioselectivity in the enzymatic reduction of aryl ketones
    • D.M. Zhu, B.E. Rios, J.D. Rozzell, and L. Hua Evaluation of substituent effects on activity and enantioselectivity in the enzymatic reduction of aryl ketones Tetrahedron-Asymmetry 16 2005 1541 1546
    • (2005) Tetrahedron-Asymmetry , vol.16 , pp. 1541-1546
    • Zhu, D.M.1    Rios, B.E.2    Rozzell, J.D.3    Hua, L.4
  • 48
    • 84870897427 scopus 로고    scopus 로고
    • Access to optically active aryl halohydrins using a substrate-tolerant carbonyl reductase discovered from Kluyveromyces thermotolerans
    • G.C. Xu, H.L. Yu, X.Y. Zhang, and J.H. Xu Access to optically active aryl halohydrins using a substrate-tolerant carbonyl reductase discovered from Kluyveromyces thermotolerans ACS Catal. 2 2012 2566 2571
    • (2012) ACS Catal. , vol.2 , pp. 2566-2571
    • Xu, G.C.1    Yu, H.L.2    Zhang, X.Y.3    Xu, J.H.4
  • 49
    • 33748530708 scopus 로고    scopus 로고
    • Enantioselective reduction of ketones with "designer cells" at high substrate concentrations: Highly efficient access to functionalized optically active alcohols
    • H. Groger, F. Chamouleau, N. Orologas, C. Rollmann, K. Drauz, W. Hummel, A. Weckbecker, and O. May Enantioselective reduction of ketones with "Designer cells" at high substrate concentrations: Highly efficient access to functionalized optically active alcohols Angew. Chem. Int. Ed. 45 2006 5677 5681
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5677-5681
    • Groger, H.1    Chamouleau, F.2    Orologas, N.3    Rollmann, C.4    Drauz, K.5    Hummel, W.6    Weckbecker, A.7    May, O.8
  • 50
    • 79751520578 scopus 로고    scopus 로고
    • Biocatalytic redox reactions for organic synthesis: Nonconventional regeneration methods
    • F. Hollmann, I.W.C.E. Arends, and K. Buehler Biocatalytic redox reactions for organic synthesis: Nonconventional regeneration methods ChemCatChem 2 2010 762 782
    • (2010) ChemCatChem , vol.2 , pp. 762-782
    • Hollmann, F.1    Arends, I.W.C.E.2    Buehler, K.3
  • 51
    • 58549099083 scopus 로고    scopus 로고
    • Stereoselective synthesis of three isomers of tert-butyl 5-hydroxy-4-methyl-3-oxohexanoate through alcohol dehydrogenase-catalyzed dynamic kinetic resolution
    • S. Ludeke, M. Richter, and M. Muller Stereoselective synthesis of three isomers of tert-butyl 5-hydroxy-4-methyl-3-oxohexanoate through alcohol dehydrogenase-catalyzed dynamic kinetic resolution Adv. Synth. Catal. 351 2009 253 259
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 253-259
    • Ludeke, S.1    Richter, M.2    Muller, M.3
  • 55
    • 84860173712 scopus 로고    scopus 로고
    • Efficient synthesis of a chiral precursor for angiotensin-converting enzyme (ACE) inhibitors in high space-time yield by a new reductase without external cofactors
    • N.D. Shen, Y. Ni, H.M. Ma, L.J. Wang, C.X. Li, G.W. Zheng, J. Zhang, and J.H. Xu Efficient synthesis of a chiral precursor for angiotensin-converting enzyme (ACE) inhibitors in high space-time yield by a new reductase without external cofactors Org. Lett. 14 2012 1982 1985
    • (2012) Org. Lett. , vol.14 , pp. 1982-1985
    • Shen, N.D.1    Ni, Y.2    Ma, H.M.3    Wang, L.J.4    Li, C.X.5    Zheng, G.W.6    Zhang, J.7    Xu, J.H.8
  • 56
    • 79956069868 scopus 로고    scopus 로고
    • A chemoenzymatic dynamic kinetic resolution approach to enantiomerically pure (R)- and (S)-duloxetine
    • A. Traff, R. Lihammar, and J.E. Backvall A chemoenzymatic dynamic kinetic resolution approach to enantiomerically pure (R)- and (S)-duloxetine J. Org. Chem. 76 2011 3917 3921
    • (2011) J. Org. Chem. , vol.76 , pp. 3917-3921
    • Traff, A.1    Lihammar, R.2    Backvall, J.E.3


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