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Volumn 34, Issue 3-4, 2004, Pages 264-269

Resolution of paroxetine precursor using different lipases: Influence of the reaction conditions on the enantioselectivity of lipases

Author keywords

Conformational engineering of Lipases; Enantioselectivity; Lipases; Paroxetine

Indexed keywords

ISOMERS; ORGANIC SOLVENTS;

EID: 0442307779     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2003.10.007     Document Type: Article
Times cited : (16)

References (44)
  • 1
    • 0036525716 scopus 로고    scopus 로고
    • Lipases as practical biocatalyst
    • Reetz M.T. Lipases as practical biocatalyst. Curr. Opin. Chem. Biol. 6:2002;145-150.
    • (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 145-150
    • Reetz, M.T.1
  • 2
    • 0035826279 scopus 로고    scopus 로고
    • Modulation of lipase properties in macro-aqueous systems by controlled enzyme immobilization: Enantioselective hydrolysis of a chiral ester by immobilized Pseudomonas lipase
    • Fernández-Lorente G., Terreni M., Mateo C., Bastida A., Fernández-Lafuente R., Dalmases P.et al. Modulation of lipase properties in macro-aqueous systems by controlled enzyme immobilization: enantioselective hydrolysis of a chiral ester by immobilized Pseudomonas lipase. Enzyme Microb. Technol. 28:2001;389-396.
    • (2001) Enzyme Microb. Technol. , vol.28 , pp. 389-396
    • Fernández-Lorente, G.1    Terreni, M.2    Mateo, C.3    Bastida, A.4    Fernández-Lafuente, R.5    Dalmases, P.6
  • 4
    • 0035038911 scopus 로고    scopus 로고
    • Cocoa butter equivalent through enzymatic interesterification of palm oil midfraction
    • Undurraga D., Markovits A., Erazo S. Cocoa butter equivalent through enzymatic interesterification of palm oil midfraction. Process Biochem. 36:2001;933-939.
    • (2001) Process Biochem. , vol.36 , pp. 933-939
    • Undurraga, D.1    Markovits, A.2    Erazo, S.3
  • 6
    • 0030249585 scopus 로고    scopus 로고
    • An applications of Nigella sativa seed lipase in oleo-chemical reactions
    • Dandik L., Asksoy H. An applications of Nigella sativa seed lipase in oleo-chemical reactions. Enzyme Microb. Technol. 19:1996;277-281.
    • (1996) Enzyme Microb. Technol. , vol.19 , pp. 277-281
    • Dandik, L.1    Asksoy, H.2
  • 7
    • 0033231527 scopus 로고    scopus 로고
    • Lipase-catalyzed solid-phase synthesis of sugar fatty acid esters: Removal of by products by azeotropic distillation
    • Yan Y., Bornscheuer U.T., Cao L., Schimd R.D. Lipase-catalyzed solid-phase synthesis of sugar fatty acid esters: removal of by products by azeotropic distillation. Enzyme Microb. Technol. 25:1999;725-728.
    • (1999) Enzyme Microb. Technol. , vol.25 , pp. 725-728
    • Yan, Y.1    Bornscheuer, U.T.2    Cao, L.3    Schimd, R.D.4
  • 8
    • 0034781716 scopus 로고    scopus 로고
    • Continuous production of acyl mannoses by immobilized lipase using a packed-bed reactor and their surfactant properties
    • Watanabe Y., Miyawaki Y., Adachi S., Nakanishi K., Matsuno R. Continuous production of acyl mannoses by immobilized lipase using a packed-bed reactor and their surfactant properties. Biochem. Eng. J. 8:2001;213-216.
    • (2001) Biochem. Eng. J. , vol.8 , pp. 213-216
    • Watanabe, Y.1    Miyawaki, Y.2    Adachi, S.3    Nakanishi, K.4    Matsuno, R.5
  • 9
    • 0032167489 scopus 로고    scopus 로고
    • Microbial lipases from versarile tools for biotechnology
    • Jaeger K.E., Reetz M.T. Microbial lipases from versarile tools for biotechnology. Trends Biotechnol. 16:1998;396-403.
    • (1998) Trends Biotechnol. , vol.16 , pp. 396-403
    • Jaeger, K.E.1    Reetz, M.T.2
  • 10
    • 0034681557 scopus 로고    scopus 로고
    • Enzymatic synthesis of derivatives of vitamin a in organic media
    • Anugard T., Legoy M.D. Enzymatic synthesis of derivatives of vitamin A in organic media. J. Mol. Catal. Part B. Enzymol. 8:2000;275-280.
    • (2000) J. Mol. Catal. Part B. Enzymol. , vol.8 , pp. 275-280
    • Anugard, T.1    Legoy, M.D.2
  • 11
    • 84978734472 scopus 로고    scopus 로고
    • Rhem HJ, Philer G, Stadler A, Kelly PJW, editors. Biotechnology, vol. 8. New York: VCH
    • Kazlauskas RJ, Bornscheuer UT. Biotransformations with lipases. In: Rhem HJ, Philer G, Stadler A, Kelly PJW, editors. Biotechnology, vol. 8. New York: VCH; 1998. p. 37-192.
    • (1998) Biotransformations with Lipases , vol.8 , pp. 37-192
    • Kazlauskas, R.J.1    Bornscheuer, U.T.2
  • 13
    • 0035843122 scopus 로고    scopus 로고
    • Enzymes for chemical synthesis
    • Koeller K.M., Wong C.H. Enzymes for chemical synthesis. Nature. 409:2001;232-240.
    • (2001) Nature , vol.409 , pp. 232-240
    • Koeller, K.M.1    Wong, C.H.2
  • 15
    • 0033976143 scopus 로고    scopus 로고
    • Directed evolution of enantio-selective enzymes for organic chemistry
    • Jaeger K.E., Reetz M.T. Directed evolution of enantio-selective enzymes for organic chemistry. Curr. Opin. Chem. Biol. 4:2002;68-73.
    • (2002) Curr. Opin. Chem. Biol. , vol.4 , pp. 68-73
    • Jaeger, K.E.1    Reetz, M.T.2
  • 16
    • 0035843122 scopus 로고    scopus 로고
    • Enzymes for chemical synthesis
    • Koeller K.M., Wong C.H. Enzymes for chemical synthesis. Nature. 409:2001;232-240.
    • (2001) Nature , vol.409 , pp. 232-240
    • Koeller, K.M.1    Wong, C.H.2
  • 20
    • 0032486523 scopus 로고    scopus 로고
    • A single step purification, immobilization and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports
    • Bastida A., Sabuquillo P., Armisen P., Fernández-Lafuente R., Huguet J., Guisán J.M. A single step purification, immobilization and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports. Biotechnol. Bioeng. 58:1998;486-493.
    • (1998) Biotechnol. Bioeng. , vol.58 , pp. 486-493
    • Bastida, A.1    Sabuquillo, P.2    Armisen, P.3    Fernández-Lafuente, R.4    Huguet, J.5    Guisán, J.M.6
  • 22
    • 0001406913 scopus 로고
    • Action de la lipase pancreatique sur les esters en emulsion
    • Sarda L., Desnuelle P. Action de la lipase pancreatique sur les esters en emulsion. Biochim. Biophys. Acta. 30:1958;513-521.
    • (1958) Biochim. Biophys. Acta , vol.30 , pp. 513-521
    • Sarda, L.1    Desnuelle, P.2
  • 25
    • 0028855057 scopus 로고
    • Role of solvents in the control of enzyme selectivity in organic media
    • Carrea G., Ottolina G., Riva S. Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol. 13:1995;63-70.
    • (1995) Trends Biotechnol. , vol.13 , pp. 63-70
    • Carrea, G.1    Ottolina, G.2    Riva, S.3
  • 26
    • 0028765249 scopus 로고
    • Lipase-catalyzed enantioselective esterification of glycidol in no-aqueous solvent: Solvent effects on enzymatic activity
    • Martins J.F., Correa de Sampaio T., Borges de Carvalho I., Barreiros S. Lipase-catalyzed enantioselective esterification of glycidol in no-aqueous solvent: solvent effects on enzymatic activity. Biotechnol. Bioeng. 44:1994;119-124.
    • (1994) Biotechnol. Bioeng. , vol.44 , pp. 119-124
    • Martins, J.F.1    Correa De Sampaio, T.2    Borges De Carvalho, I.3    Barreiros, S.4
  • 27
    • 0034610172 scopus 로고    scopus 로고
    • Solvent effect on lipase enantioselectivity. Evidence for the presence of two thermodynamic states
    • Overbeeke P.L.A., Jongejan J.A., Heijnen J.J. Solvent effect on lipase enantioselectivity. Evidence for the presence of two thermodynamic states. Biotchnol. Bioeng. 70:2000;278-290.
    • (2000) Biotchnol. Bioeng. , vol.70 , pp. 278-290
    • Overbeeke, P.L.A.1    Jongejan, J.A.2    Heijnen, J.J.3
  • 28
    • 0000858214 scopus 로고
    • Control of enzyme enantioselectivity by the reaction medium
    • Sakurai T., Margolin A.L., Klibanov A.M. Control of enzyme enantioselectivity by the reaction medium. J. Am. Chem. Soc. 110:1988;7236-7237.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7236-7237
    • Sakurai, T.1    Margolin, A.L.2    Klibanov, A.M.3
  • 29
  • 31
    • 0037190853 scopus 로고    scopus 로고
    • Enantioselective synthesis of NK-1 receptor antagonists (+)-CP-99,994 and (+)-CP-122,721
    • Yamazaki N., Atobe M., Kibayashi C. Enantioselective synthesis of NK-1 receptor antagonists (+)-CP-99,994 and (+)-CP-122,721. Tetrahedron Lett. 43:2002;7979-7982.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7979-7982
    • Yamazaki, N.1    Atobe, M.2    Kibayashi, C.3
  • 32
    • 0037009287 scopus 로고    scopus 로고
    • Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes
    • Amy L.B., Sari I., Dean W., Cheryl K.-S., Naijue Z., Mark L.T. Synthesis and dopamine transporter binding affinities of 3α-benzyl-8- (diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes. Bioorg. Med. Chem. Lett. 12:2002;2387-2390.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2387-2390
    • Amy, L.B.1    Sari, I.2    Dean, W.3    Cheryl, K.-S.4    Naijue, Z.5    Mark, L.T.6
  • 33
    • 0035842879 scopus 로고    scopus 로고
    • Diastereoselective synthesis of 4-substituted 5-(p-tolylsulfinyl)-5,6- dehydropiperidin-2-ones. A new approach to methyl L-(2S,4S)-4-methyl-6- oxopipecolate
    • Acherki H., Alvarez-Ibarra C., de Dios A., Gutiérrez M., Quiroga M.L. Diastereoselective synthesis of 4-substituted 5-(p-tolylsulfinyl)-5,6- dehydropiperidin-2-ones. A new approach to methyl L-(2S,4S)-4-methyl-6- oxopipecolate. Tetrahedron: Asymmetry. 12:2001;3173-3183.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3173-3183
    • Acherki, H.1    Alvarez-Ibarra, C.2    De Dios, A.3    Gutiérrez, M.4    Quiroga, M.L.5
  • 34
    • 0034702555 scopus 로고    scopus 로고
    • Asymmetric synthesis of (-)-paroxetine using PLE hydrolysis
    • Yu M.S., Lantos I., Peng Z.-Q., Yu J., Cacchio T. Asymmetric synthesis of (-)-paroxetine using PLE hydrolysis. Tetrahedron Lett. 41:2000;5647-5651.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5647-5651
    • Yu, M.S.1    Lantos, I.2    Peng, Z.-Q.3    Yu, J.4    Cacchio, T.5
  • 35
    • 0001571086 scopus 로고
    • Asymmetric synthesis of β-substituted alcanoic acids via highly stereoselective conjugate additions of organocopper compounds to chiral enoates
    • Helmchen G., Wegner G. Asymmetric synthesis of β-substituted alcanoic acids via highly stereoselective conjugate additions of organocopper compounds to chiral enoates. Tetrahedron Lett. 26(49):1985;6051-6054.
    • (1985) Tetrahedron Lett. , vol.26 , Issue.49 , pp. 6051-6054
    • Helmchen, G.1    Wegner, G.2
  • 37
    • 0029164289 scopus 로고
    • Synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates
    • Urban E., Knühl G., Helmchen G. Synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates. Tetrahedron Lett. 40(36):1995;7229- 7232.
    • (1995) Tetrahedron Lett. , vol.40 , Issue.36 , pp. 7229-7232
    • Urban, E.1    Knühl, G.2    Helmchen, G.3
  • 38
    • 85030910793 scopus 로고    scopus 로고
    • Christensen JA, Squires, RF. US Patent 3912743 (1975).
    • Christensen JA, Squires, RF. US Patent 3912743 (1975).
  • 39
    • 85030907941 scopus 로고    scopus 로고
    • Christensen JA, Squires, RF. US Patent 4007196 (1977).
    • Christensen JA, Squires, RF. US Patent 4007196 (1977).
  • 40
    • 85030913099 scopus 로고    scopus 로고
    • Faruk EA, Martin RT. US Patent 4902801 (1990).
    • Faruk EA, Martin RT. US Patent 4902801 (1990).
  • 41
    • 85030904022 scopus 로고    scopus 로고
    • Borza I, Czibula L, Dobay L, Harsanyi K, Hegedues I, Kreidl J, et al. WO Patent 98/01424 (1998).
    • Borza I, Czibula L, Dobay L, Harsanyi K, Hegedues I, Kreidl J, et al. WO Patent 98/01424 (1998).
  • 42
    • 0030009989 scopus 로고    scopus 로고
    • Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine
    • Amat M., Hidalgo J., Bosch J. Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine. Tetrahedron: Asymmetry. 7:1996;1591-1594.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1591-1594
    • Amat, M.1    Hidalgo, J.2    Bosch, J.3
  • 43
    • 0035968995 scopus 로고    scopus 로고
    • A short formal synthesis of paroxetine. Diastereoselective cuprate addition to a chiral racemic olefinic amido ester
    • Cossy J., Mirguet O., Gomez Pardo D., Desmurs J.-R. A short formal synthesis of paroxetine. Diastereoselective cuprate addition to a chiral racemic olefinic amido ester. Tetrahedron Lett. 42:2001;7805-7807.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7805-7807
    • Cossy, J.1    Mirguet, O.2    Gomez Pardo, D.3    Desmurs, J.-R.4
  • 44
    • 0017184389 scopus 로고
    • A rapid and the sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye-binding
    • Bradford M.M. A rapid and the sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye-binding. Anal. Biochem. 72:1976;248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1


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