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      KCI등재 SCIE SCOPUS

      Enantioselective Esterification of Ibuprofen by a Novel Thermophilic Biocatalyst: APE1547

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      https://www.riss.kr/link?id=A103818739

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      다국어 초록 (Multilingual Abstract)

      The enantioselective esterification of ibuprofen catalyzed by a novel thermophilic esterase (APE1547)from the archaeon Aeropyrum pernix K1 was successfully conducted in organic solvents. The effects of acyl acceptor,substrate ratio, organic solvent, t...

      The enantioselective esterification of ibuprofen catalyzed by a novel thermophilic esterase (APE1547)from the archaeon Aeropyrum pernix K1 was successfully conducted in organic solvents. The effects of acyl acceptor,substrate ratio, organic solvent, temperature, and water activity were investigated. Under optimum conditions, the highest enantioselectivity (E = 38.1) was obtained with a higher enzyme activity (216.5 μmol/g/h). Celites were added into the reaction mixture to remove the water produced in the esterification. The reaction achieved its equilibrium in approximately 96 h with a conversion of 57 and 99%(ee) of the un-reacted (S)-ibuprofen obtained.

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      참고문헌 (Reference)

      1 Holmquist, M., "structural basis for enantioselective inhibition of Candida rugosa lipase by long-chain aliphatic alcohols" 5 : 83-88, 1996

      2 Mustranta, A., "Use of lipases in the resolution of racemic ibuprofen" 38 : 61-66, 1992

      3 Zamost, B. L., "Thermostable enzymes for industrial applications" 8 : 71-82, 1991

      4 Wang, Z., "The effect of microwater on the enzyme-catalyzed reaction in organic media and its controlling methods" 12 : 130-134, 2002

      5 Phillips, R. S., "Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation" 14 : 13-16, 1996

      6 Zhang, G. R., "Study on the relationship between structure and enantioselectivity of a hyperthermophilic esterase from archaeon Aeropyrum pernix K1" 38 : 148-153, 2006

      7 Wei, X. F., "Study on the enzymatic Michael addition in ionic liquids" 23 : 273-276, 2009

      8 Rao, L., "Study on a specific site tyr444 on a hyperthermophilic enzyme APE1547" 25 : 353-356, 1547

      9 Pan, S. H., "Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent: Effects of alcohol chain length" 34 : 47-51, 1990

      10 Kobayashi, T, "Reaction equilibrium for lipase-catalyzed condensation in organic solvent systems" 26 : 1461-1468, 2004

      1 Holmquist, M., "structural basis for enantioselective inhibition of Candida rugosa lipase by long-chain aliphatic alcohols" 5 : 83-88, 1996

      2 Mustranta, A., "Use of lipases in the resolution of racemic ibuprofen" 38 : 61-66, 1992

      3 Zamost, B. L., "Thermostable enzymes for industrial applications" 8 : 71-82, 1991

      4 Wang, Z., "The effect of microwater on the enzyme-catalyzed reaction in organic media and its controlling methods" 12 : 130-134, 2002

      5 Phillips, R. S., "Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation" 14 : 13-16, 1996

      6 Zhang, G. R., "Study on the relationship between structure and enantioselectivity of a hyperthermophilic esterase from archaeon Aeropyrum pernix K1" 38 : 148-153, 2006

      7 Wei, X. F., "Study on the enzymatic Michael addition in ionic liquids" 23 : 273-276, 2009

      8 Rao, L., "Study on a specific site tyr444 on a hyperthermophilic enzyme APE1547" 25 : 353-356, 1547

      9 Pan, S. H., "Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent: Effects of alcohol chain length" 34 : 47-51, 1990

      10 Kobayashi, T, "Reaction equilibrium for lipase-catalyzed condensation in organic solvent systems" 26 : 1461-1468, 2004

      11 Chen, C. S., "Quantitative analyses of biochemical kinetic resolutions of enantiomers" 104 : 7294-7299, 1982

      12 Adams, S. S., "Pharmacological difference between the optical isomers of ibuprofen: Evidence for metabolic inversion of the (−) isomer" 28 : 156-157, 1976

      13 Gorman, L. A. S, "Organic solvents strip water off enzymes" 39 : 392-397, 1992

      14 Won, K., "Lipasecatalyzed enantioselective esterification of racemic ibuprofen coupled with pervaporation" 264-269, 2006

      15 Ducret, A., "Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity" 22 : 212-216, 1998

      16 D bkowska, K, "Influence of temperature on the activity and enantioselectivity of Burkholderia cepacia lipase in the kinetic resolution of mandelic acid enantiomers" 46 : 147-153, 2009

      17 Wu, J. Y, "Influence of alcohol concentration on lipase catalyzed enantioselective esterification of racemic naproxen in isooctane: Under controlled water activity" 26 : 124-130, 2000

      18 Fitzpatrick, P. A, "How can the solvent affect enzyme enantioselectivity" 113 : 3166-3171, 1991

      19 Sánchez, A., "Highly enantioselective esterification of racemic ibuprofen in a packed bed reactor using immobilized Rhizomucor miehei lipase" 27 : 157-166, 2000

      20 Zhang, G. R., "High-throughput screening of the enantioselectivity of hyperthermophilic mutant esterases from Archaeon Aeropyrum pernix K1 for resolution of (R, S)-2-octanol acetate" 23 : 319-324, 2007

      21 Contesini, F. J, "Esterification of (R S)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids" 17 : 2069-2073, 2006

      22 Serdakowski, A. L, "Enzyme activation for organic solvents made easy" 26 : 48-54, 2008

      23 Tsai, S. W., "Enzymatic synthesis of (S) -ibuprofen ester prodrug from racemic ibuprofen by lipase in organic solvents" 13 : 82-88, 1997

      24 Goto, M., "Enzymatic resolution of racemic ibuprofen by surfactant-coated lipases in organic media" 18 : 839-844, 2004

      25 Foresti, M. L., "Enantioselective esterification of ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: Experimental and molecular modeling aspects" 84 : 1461-1473, 2009

      26 López-Belmonte, M. T., "Enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized Rhizomucor miehei lipase" 62 : 1831-1840, 1997

      27 Liu, Y., "Effects of alcohol and solvent on the performance of lipase from Candida sp. in enantioselective esterification of racemic ibuprofen" 56 : 126-130, 2009

      28 Canaparo, R., "Determination of Ibuprofen in human plasma by high performance liquid chromatography: Validation and application in pharmacokinetic study" 14 : 219-226, 2000

      29 Gao, R. J., "Denaturing effects of urea and guanidine hydrochloride on hyperthermophilic esterase from Aeropyrum penix K1" 22 : 168-172, 2006

      30 Bartlam, M., "Crystal structure of an acylpeptide hydrolase/esterase from Aeropyrum pernix K1" 12 : 1481-1488, 2004

      31 Berglund, P., "Controlling lipase enantioselectivity for organic synthesis" 18 : 13-22, 2001

      32 Gao, R. J., "Cloning, purification and properties of a hyperthermophilic esterase from archaeon Aeropyrum pernix K1" 24 : 1-8, 2003

      33 Schulze, B, "Biocatalysis for industrial production of fine chemicals" 10 : 609-615, 1999

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      2020-01-01 평가 등재학술지 유지 (해외등재 학술지 평가) KCI등재
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      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 1.14 0.13 0.75
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      0.57 0.46 0.239 0.02
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