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Volumn 86, Issue 5, 2011, Pages 739-748

Optimization and kinetic modeling of lipase catalyzed enantioselective N-acetylation of ( ±)-1-phenylethylamine under microwave irradiation

Author keywords

( ) 1 phenylethylamine; (R) N (1 phenylethyl) acetamide; Kinetic resolution; Microwave irradiation; Novozyme 435; Response surface methodology

Indexed keywords

(R)-N-(1-PHENYLETHYL) ACETAMIDE; 1-PHENYLETHYLAMINE; KINETIC RESOLUTION; NOVOZYME 435; RESPONSE SURFACE METHODOLOGY;

EID: 79953726278     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.2582     Document Type: Article
Times cited : (30)

References (24)
  • 1
    • 22544466988 scopus 로고    scopus 로고
    • Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation
    • Arseniyadis S, Subhash PV, Valleix A, Wagner A Mioskowski C, Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation. Chem Commun 26: 3310-3312 (2005).
    • (2005) Chem Commun , vol.26 , pp. 3310-3312
    • Arseniyadis, S.1    Subhash, P.V.2    Valleix, A.3    Wagner, A.4    Mioskowski, C.5
  • 2
    • 33745743031 scopus 로고    scopus 로고
    • Enzymatic aminolysis and ammonolysis processes in the preparation of chiral nitrogenated compounds
    • Gotor-Ferna'ndez V Gotor V, Enzymatic aminolysis and ammonolysis processes in the preparation of chiral nitrogenated compounds. Curr Org Chem 10: 1125-1143 (2006).
    • (2006) Curr Org Chem , vol.10 , pp. 1125-1143
    • Gotor-Ferna'ndez, V.1    Gotor, V.2
  • 3
    • 33846209146 scopus 로고    scopus 로고
    • Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds
    • Ghanem A, Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 63: 1721-1754 (2007).
    • (2007) Tetrahedron , vol.63 , pp. 1721-1754
    • Ghanem, A.1
  • 4
    • 0001484267 scopus 로고
    • Enantioselectivity of Candida rugosa lipase toward carboxylic acids: a predictive rule from substrate mapping and X-ray crystallography
    • Ahmed SN, Kazlauskas RJ, Morinville AH, Grochulski P, Schrag JD Cygler M, Enantioselectivity of Candida rugosa lipase toward carboxylic acids: a predictive rule from substrate mapping and X-ray crystallography. Biocatalysis 9: 209-225 (1994).
    • (1994) Biocatalysis , vol.9 , pp. 209-225
    • Ahmed, S.N.1    Kazlauskas, R.J.2    Morinville, A.H.3    Grochulski, P.4    Schrag, J.D.5    Cygler, M.6
  • 5
    • 0034697072 scopus 로고    scopus 로고
    • Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches
    • Villeneuve P, Muderhwa JM, Graille J Haas MJ, Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches. J Mol Catal B: Enzym 9: 113-148 (2000).
    • (2000) J Mol Catal B: Enzym , vol.9 , pp. 113-148
    • Villeneuve, P.1    Muderhwa, J.M.2    Graille, J.3    Haas, M.J.4
  • 6
    • 34047208469 scopus 로고    scopus 로고
    • Microwave energy: a versatile tool for bioscience
    • Collins JM Leadbeater NE, Microwave energy: a versatile tool for bioscience. Org Biomol Chem 5: 1141-1150 (2007).
    • (2007) Org Biomol Chem , vol.5 , pp. 1141-1150
    • Collins, J.M.1    Leadbeater, N.E.2
  • 7
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • Kappe CO, Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed 43: 6250-6284 (2004).
    • (2004) Angew Chem Int Ed , vol.43 , pp. 6250-6284
    • Kappe, C.O.1
  • 8
    • 14644427257 scopus 로고    scopus 로고
    • Microwaves in organic synthesis. Thermal and non- thermal microwave effects
    • de la Hoz A, Diaz-Ortiz Á Moreno A, Microwaves in organic synthesis. Thermal and non- thermal microwave effects. Chem Soc Rev 34: 164-178 (2005).
    • (2005) Chem Soc Rev , vol.34 , pp. 164-178
    • de la Hoz, A.1    Diaz-Ortiz, A.2    Moreno, A.3
  • 9
    • 34547211227 scopus 로고    scopus 로고
    • The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols
    • Bachu P, Gibson JS, Sperry J Brimble MA, The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols. Tetrahedron Asym 18: 1618-1624 (2007).
    • (2007) Tetrahedron Asym , vol.18 , pp. 1618-1624
    • Bachu, P.1    Gibson, J.S.2    Sperry, J.3    Brimble, M.A.4
  • 10
    • 0000153467 scopus 로고    scopus 로고
    • Microwave-promoted lipase-catalyzed reactions. resolution of ( ±)-1-Phenylethanol
    • Carrilo-Munoz JR, Bouvet D, Guibé-Jampel E, Loupy A Petit A, Microwave-promoted lipase-catalyzed reactions. resolution of ( ±)-1-Phenylethanol. J Org Chem 61: 7746-7749 (1996).
    • (1996) J Org Chem , vol.61 , pp. 7746-7749
    • Carrilo-Munoz, J.R.1    Bouvet, D.2    Guibé-Jampel, E.3    Loupy, A.4    Petit, A.5
  • 11
    • 20544468709 scopus 로고    scopus 로고
    • Room temperature ionic liquids in the kinetic resolution of adrenaline-type aminoethanols by burkholderia cepacia lipase under normal and microwave conditions
    • Lundell K, Kurki T, Lindroos M Kanerva LT, Room temperature ionic liquids in the kinetic resolution of adrenaline-type aminoethanols by burkholderia cepacia lipase under normal and microwave conditions. Adv Synth Catal 347: 1110-1118 (2005).
    • (2005) Adv Synth Catal , vol.347 , pp. 1110-1118
    • Lundell, K.1    Kurki, T.2    Lindroos, M.3    Kanerva, L.T.4
  • 12
    • 41449087935 scopus 로고    scopus 로고
    • Microwave-promoted racemization and dynamic kinetic resolution of chiral amines over Pd on alkaline earth supports and lipases
    • Parvulescu AN, Eycken EV, Jacobs PA De Vos DE, Microwave-promoted racemization and dynamic kinetic resolution of chiral amines over Pd on alkaline earth supports and lipases. J Catal 255: 206-212 (2008).
    • (2008) J Catal , vol.255 , pp. 206-212
    • Parvulescu, A.N.1    Eycken, E.V.2    Jacobs, P.A.3    De Vos, D.E.4
  • 13
    • 34547933047 scopus 로고    scopus 로고
    • A chemo-enzymatic process for sequential kinetic resolution of (R,S)-2-octanol under microwave irradiation
    • Yu D, Chen P, Wang L, Gu Q, Li Y Wang Z, et al, A chemo-enzymatic process for sequential kinetic resolution of (R, S)-2-octanol under microwave irradiation. Process Biochem 42: 1312-1318 (2007).
    • (2007) Process Biochem , vol.42 , pp. 1312-1318
    • Yu, D.1    Chen, P.2    Wang, L.3    Gu, Q.4    Li, Y.5    Wang, Z.6
  • 14
    • 4544284955 scopus 로고    scopus 로고
    • Applications of microwaves in biological sciences
    • Roy I Gupta MN, Applications of microwaves in biological sciences Curr Sci 85: 1685-1693 (2003).
    • (2003) Curr Sci , vol.85 , pp. 1685-1693
    • Roy, I.1    Gupta, M.N.2
  • 15
    • 33748969391 scopus 로고    scopus 로고
    • Influence of microwave irradiation on free candida antartica lipase b activity and stability
    • Réjasse B, BessonEn T, Legoy MD Lamare S, Influence of microwave irradiation on free candida antartica lipase b activity and stability. Org Biomol Chem 4: 3703-3707 (2004).
    • (2004) Org Biomol Chem , vol.4 , pp. 3703-3707
    • Réjasse, B.1    BessonEn, T.2    Legoy, M.D.3    Lamare, S.4
  • 16
    • 0030580312 scopus 로고    scopus 로고
    • Microwave radiation can increase the rate of enzyme-catalysed reactions in organic media
    • Parker MC, Besson T, Lamare S Legoy MD, Microwave radiation can increase the rate of enzyme-catalysed reactions in organic media. Tetrahedron Lett 37: 8383-8386 (1996).
    • (1996) Tetrahedron Lett , vol.37 , pp. 8383-8386
    • Parker, M.C.1    Besson, T.2    Lamare, S.3    Legoy, M.D.4
  • 17
    • 0035742307 scopus 로고    scopus 로고
    • Reactivity and selectivity under microwaves in organic chemistry. Relation with medium effects and reaction mechanisms
    • Loupy A, Perreux L, Marion L, Burle K Moneuse M, Reactivity and selectivity under microwaves in organic chemistry. Relation with medium effects and reaction mechanisms. Pure Appl Chem 73: 161-166 (2001).
    • (2001) Pure Appl Chem , vol.73 , pp. 161-166
    • Loupy, A.1    Perreux, L.2    Marion, L.3    Burle, K.4    Moneuse, M.5
  • 18
    • 7444256582 scopus 로고    scopus 로고
    • Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols
    • Yadav GD Lathi PS, Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols. J Mol Catal A: Chem 223: 51-56 (2004).
    • (2004) J Mol Catal A: Chem , vol.223 , pp. 51-56
    • Yadav, G.D.1    Lathi, P.S.2
  • 19
    • 21044435532 scopus 로고    scopus 로고
    • Synergism of microwave and immobilized enzyme catalysis in synthesis of adipic acid esters in non-aqueous media
    • Yadav GD Lathi PS, Synergism of microwave and immobilized enzyme catalysis in synthesis of adipic acid esters in non-aqueous media. Synth Commun 35: 1699-1705 (2005).
    • (2005) Synth Commun , vol.35 , pp. 1699-1705
    • Yadav, G.D.1    Lathi, P.S.2
  • 20
    • 33645558623 scopus 로고    scopus 로고
    • Kinetic modeling of microwave assisted chemo-enzymatic epoxidation of styrene to styrene oxide
    • Yadav GD Borkar IV, Kinetic modeling of microwave assisted chemo-enzymatic epoxidation of styrene to styrene oxide. AIChE J 52: 1235-1247 (2006).
    • (2006) AIChE J , vol.52 , pp. 1235-1247
    • Yadav, G.D.1    Borkar, I.V.2
  • 21
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen CS, Fujimoto Y, Girdaukas G Sih CJ, Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104: 7294-7299 (1982).
    • (1982) J Am Chem Soc , vol.104 , pp. 7294-7299
    • Chen, C.S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 22
    • 79953707959 scopus 로고    scopus 로고
    • Novo Nordisk Product Sheet for Novozyme 435, Lipozyme RM IM and Lipozyme TL IM.
    • Novo Nordisk Product Sheet for Novozyme 435, Lipozyme RM IM and Lipozyme TL IM.
  • 23
    • 33646867639 scopus 로고    scopus 로고
    • Lipases: useful biocatalysts for the preparation of pharmaceuticals
    • Gotor-Fernández V, Brieva R Gotor V, Lipases: useful biocatalysts for the preparation of pharmaceuticals. J Mol Catal B: Enzym 40: 111-120 (2006).
    • (2006) J Mol Catal B: Enzym , vol.40 , pp. 111-120
    • Gotor-Fernández, V.1    Brieva, R.2    Gotor, V.3
  • 24
    • 0003518480 scopus 로고
    • Wiley/Interscience, New York
    • Segel IH, Enzyme Kinetics. Wiley/Interscience, New York (1975).
    • (1975) Enzyme Kinetics
    • Segel, I.H.1


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