메뉴 건너뛰기




Volumn 43, Issue 12, 2008, Pages 1419-1426

Optimisation of stabilised Carboxylesterase NP for enantioselective hydrolysis of naproxen methyl ester

Author keywords

Carboxylesterase NP; Conversion; Enantiomeric excess; Naproxen methyl ester (NME); S naproxen

Indexed keywords

ACIDS; CHIRALITY; DRUG PRODUCTS; ENANTIOMERS; ENZYME INHIBITION; ENZYMES; ESTERIFICATION; ESTERS; FATTY ACIDS; FORMALDEHYDE; HYDROLYSIS; NUCLEAR PROPULSION; ORGANIC COMPOUNDS; REACTION KINETICS; REACTION RATES; SODIUM; SODIUM COMPOUNDS; SUBSTRATES; SURFACE ACTIVE AGENTS;

EID: 54949154818     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2008.09.001     Document Type: Article
Times cited : (22)

References (29)
  • 1
    • 84987223437 scopus 로고
    • Preparation of optically pure 2-aryl- and 2-aryloxy-propionates by selective enzymatic hydrolysis
    • Mutsaers J.H.G.M., and Kooreman H.J. Preparation of optically pure 2-aryl- and 2-aryloxy-propionates by selective enzymatic hydrolysis. Recl Trav Chim Pays-Bas 110 (1991) 185-188
    • (1991) Recl Trav Chim Pays-Bas , vol.110 , pp. 185-188
    • Mutsaers, J.H.G.M.1    Kooreman, H.J.2
  • 2
    • 0026221188 scopus 로고
    • Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor
    • Battistel E., Bianchi D., Cesti P., and Pina C. Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor. Biotechnol Bioeng 38 (1991) 659-664
    • (1991) Biotechnol Bioeng , vol.38 , pp. 659-664
    • Battistel, E.1    Bianchi, D.2    Cesti, P.3    Pina, C.4
  • 3
    • 1842473615 scopus 로고    scopus 로고
    • Enzyme catalysed deracemisation and dynamic kinetic resolution reactions
    • Turner N.J. Enzyme catalysed deracemisation and dynamic kinetic resolution reactions. Curr Opin Chem Biol 8 (2004) 114-119
    • (2004) Curr Opin Chem Biol , vol.8 , pp. 114-119
    • Turner, N.J.1
  • 4
    • 33751499686 scopus 로고
    • A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalysed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa
    • Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., and Cuccia L.A. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalysed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J Org Chem 56 (1991) 2656-2665
    • (1991) J Org Chem , vol.56 , pp. 2656-2665
    • Kazlauskas, R.J.1    Weissfloch, A.N.E.2    Rappaport, A.T.3    Cuccia, L.A.4
  • 5
    • 0029060763 scopus 로고
    • Cross-linked crystals of Candida rugosa lipase: highly efficient catalysts for the resolution of chiral esters
    • Lalonde J.J., Govardhan C., Khalaf N., Martinez A.G., Visuri K., and Margolin A.L. Cross-linked crystals of Candida rugosa lipase: highly efficient catalysts for the resolution of chiral esters. J Am Chem Soc 117 (1995) 6845-6852
    • (1995) J Am Chem Soc , vol.117 , pp. 6845-6852
    • Lalonde, J.J.1    Govardhan, C.2    Khalaf, N.3    Martinez, A.G.4    Visuri, K.5    Margolin, A.L.6
  • 6
    • 0004267579 scopus 로고
    • Chibata J. (Ed), Kodansho-Halsted Press, Tokyo-New York
    • In: Chibata J. (Ed). Immobilised enzymes (1978), Kodansho-Halsted Press, Tokyo-New York
    • (1978) Immobilised enzymes
  • 8
    • 33846197938 scopus 로고    scopus 로고
    • Biocatalysis for pharmaceutical intermediates: the future is now
    • Pollard D.J., and Woodley J.M. Biocatalysis for pharmaceutical intermediates: the future is now. Trends Biotechnol 25 (2007) 66-73
    • (2007) Trends Biotechnol , vol.25 , pp. 66-73
    • Pollard, D.J.1    Woodley, J.M.2
  • 9
    • 4243794106 scopus 로고
    • The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks
    • Santaniello E., Ferraboschi P., Grisent P., and Manzocchi A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem Rev 92 (1992) 1070-1140
    • (1992) Chem Rev , vol.92 , pp. 1070-1140
    • Santaniello, E.1    Ferraboschi, P.2    Grisent, P.3    Manzocchi, A.4
  • 10
    • 0028922019 scopus 로고
    • Enantioselective hydrolysis of ethyl 2-hydroxyalkanoates by an extracellular esterase from a Bacillus sphaericus strain
    • Jackson M.A., Labeda D.P., and Becker L.A. Enantioselective hydrolysis of ethyl 2-hydroxyalkanoates by an extracellular esterase from a Bacillus sphaericus strain. Enz Microb Technol 17 (1995) 175-179
    • (1995) Enz Microb Technol , vol.17 , pp. 175-179
    • Jackson, M.A.1    Labeda, D.P.2    Becker, L.A.3
  • 11
    • 0015142128 scopus 로고
    • Antiinflammatory and analgesic properties of d-2-(6′-methoxy-2-naphtyl)propionic acid (naproxen)
    • Roszkowski A.P., Rooks W.H., Tomolonis A.J., and Miller L.M. Antiinflammatory and analgesic properties of d-2-(6′-methoxy-2-naphtyl)propionic acid (naproxen). J Pharmacol Exp Ther 179 (1971) 114-123
    • (1971) J Pharmacol Exp Ther , vol.179 , pp. 114-123
    • Roszkowski, A.P.1    Rooks, W.H.2    Tomolonis, A.J.3    Miller, L.M.4
  • 12
    • 0031172576 scopus 로고    scopus 로고
    • A facile enzymatic process for the preparation of (S)-naproxen ester prodrug in organic solvents
    • Chang C.-S., and Tsai S.-W. A facile enzymatic process for the preparation of (S)-naproxen ester prodrug in organic solvents. Enz Microbiol Technol 20 (1997) 635-639
    • (1997) Enz Microbiol Technol , vol.20 , pp. 635-639
    • Chang, C.-S.1    Tsai, S.-W.2
  • 13
    • 0028764609 scopus 로고
    • Effect of solvent on enantioselective esterification of naproxen by lipase with trimethylsilyl methanol
    • Tsai S.-W., and Wei H.-J. Effect of solvent on enantioselective esterification of naproxen by lipase with trimethylsilyl methanol. Biotechnol Bioeng 43 (1994) 64-68
    • (1994) Biotechnol Bioeng , vol.43 , pp. 64-68
    • Tsai, S.-W.1    Wei, H.-J.2
  • 14
    • 0028026137 scopus 로고
    • Kinetics of enantioselective esterification of naproxen by lipase in organic solvents
    • Tsai S.-W., and Wei H.-J. Kinetics of enantioselective esterification of naproxen by lipase in organic solvents. Biocatalysis 11 (1994) 33-45
    • (1994) Biocatalysis , vol.11 , pp. 33-45
    • Tsai, S.-W.1    Wei, H.-J.2
  • 15
    • 0028015905 scopus 로고
    • Comparison of the enzymatic activity of commercial and semipurified lipase of Candida cylindracea in the hydrolysis of the esters of (R,S)-2-aryl propionic acids
    • Hernaiz M.J., Sanchez-Montero J.M., and Siniserra J.V. Comparison of the enzymatic activity of commercial and semipurified lipase of Candida cylindracea in the hydrolysis of the esters of (R,S)-2-aryl propionic acids. Tetrahedron 50 (1994) 10749-10760
    • (1994) Tetrahedron , vol.50 , pp. 10749-10760
    • Hernaiz, M.J.1    Sanchez-Montero, J.M.2    Siniserra, J.V.3
  • 16
    • 0025284519 scopus 로고
    • Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification
    • Wu S.-H., Guo Z.-W., and Sih C.J. Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification. J Am Chem Soc 112 (1990) 1990-1995
    • (1990) J Am Chem Soc , vol.112 , pp. 1990-1995
    • Wu, S.-H.1    Guo, Z.-W.2    Sih, C.J.3
  • 17
    • 34247279313 scopus 로고    scopus 로고
    • An innovative approach to improve the performance of a two separate phase enzyme membrane reactor by immobilizing lipase in presence of emulsion
    • Giorno L., D'Amore E., Mazzei R., Piacentini E., Zhang J., Driolo E., et al. An innovative approach to improve the performance of a two separate phase enzyme membrane reactor by immobilizing lipase in presence of emulsion. J Membr Sci 295 (2007) 95-101
    • (2007) J Membr Sci , vol.295 , pp. 95-101
    • Giorno, L.1    D'Amore, E.2    Mazzei, R.3    Piacentini, E.4    Zhang, J.5    Driolo, E.6
  • 18
    • 9944237836 scopus 로고    scopus 로고
    • Carica papaya lipase: a novel biocatalyst for the enantioselective hydrolysis of (R,S)-naproxen 2,2,2-trifluoroethyl ester
    • Chen C.-C., and Tsai S.-W. Carica papaya lipase: a novel biocatalyst for the enantioselective hydrolysis of (R,S)-naproxen 2,2,2-trifluoroethyl ester. Enz Microb Technol 36 (2005) 127-132
    • (2005) Enz Microb Technol , vol.36 , pp. 127-132
    • Chen, C.-C.1    Tsai, S.-W.2
  • 20
    • 0028305905 scopus 로고
    • Development of a new Bacillus carboxyl esterase for use in the resolution of chiral drugs
    • Quax W.J., and Broekhuizen C.P. Development of a new Bacillus carboxyl esterase for use in the resolution of chiral drugs. Appl Microbiol Biotechnol 41 (1994) 425-431
    • (1994) Appl Microbiol Biotechnol , vol.41 , pp. 425-431
    • Quax, W.J.1    Broekhuizen, C.P.2
  • 21
    • 13844296695 scopus 로고    scopus 로고
    • Comparison and functional characterisation of three homologous intracellular carboxylesterases of Bacillus subtilis
    • Dröge M.J., Bos R., Boersma Y.L., and Quax W.J. Comparison and functional characterisation of three homologous intracellular carboxylesterases of Bacillus subtilis. J Mol Catal B-Enz 32 (2005) 261-270
    • (2005) J Mol Catal B-Enz , vol.32 , pp. 261-270
    • Dröge, M.J.1    Bos, R.2    Boersma, Y.L.3    Quax, W.J.4
  • 22
    • 0034851618 scopus 로고    scopus 로고
    • Paralogous gene analysis reveals a highly enantioselective 1,2-O-isopropylideneglycerol caprylate esterase of Bacillus subtilis
    • Dröge M.J., Bos R., and Quax W.J. Paralogous gene analysis reveals a highly enantioselective 1,2-O-isopropylideneglycerol caprylate esterase of Bacillus subtilis. Eur J Biochem 268 (2001) 3332-3338
    • (2001) Eur J Biochem , vol.268 , pp. 3332-3338
    • Dröge, M.J.1    Bos, R.2    Quax, W.J.3
  • 23
    • 0033134185 scopus 로고    scopus 로고
    • Integration of reaction and separation in manufacturing of pharmaceuticals: membrane-mediated production of S-Ibuprofen
    • Cauwenberg V., Vergossen P., Stankiewicz A., and Kierkels H. Integration of reaction and separation in manufacturing of pharmaceuticals: membrane-mediated production of S-Ibuprofen. Chem Eng Sci 54 (1999) 1473-1477
    • (1999) Chem Eng Sci , vol.54 , pp. 1473-1477
    • Cauwenberg, V.1    Vergossen, P.2    Stankiewicz, A.3    Kierkels, H.4
  • 24
    • 54949087917 scopus 로고    scopus 로고
    • Mutsaers JHGM, van der Laken CJ, Broekhuizen CP, Quax WJ. Stabilisation of carboxyl esterase. 1996 [US5538876].
    • Mutsaers JHGM, van der Laken CJ, Broekhuizen CP, Quax WJ. Stabilisation of carboxyl esterase. 1996 [US5538876].
  • 25
    • 0037416732 scopus 로고    scopus 로고
    • Screening of commercial enzymes for the enantioselective hydrolysis of R,S-naproxen
    • Steenkamp L., and Brady D. Screening of commercial enzymes for the enantioselective hydrolysis of R,S-naproxen. Enz Microb Technol 32 (2003) 472-477
    • (2003) Enz Microb Technol , vol.32 , pp. 472-477
    • Steenkamp, L.1    Brady, D.2
  • 26
    • 0442276344 scopus 로고    scopus 로고
    • Optimisation of the enantioselective biocatalytic hydrolysis of naproxen ethyl ester using ChiroCLEC-CR
    • Brady D., Steenkamp L., Skein E., Chaplin J.A., and Reddy S. Optimisation of the enantioselective biocatalytic hydrolysis of naproxen ethyl ester using ChiroCLEC-CR. Enz Microb Technol 34 (2004) 283-291
    • (2004) Enz Microb Technol , vol.34 , pp. 283-291
    • Brady, D.1    Steenkamp, L.2    Skein, E.3    Chaplin, J.A.4    Reddy, S.5
  • 27
    • 0343035685 scopus 로고    scopus 로고
    • Simple dissolution-reaction model for enzymatic conversion of suspension of solid substrate
    • Wolff A., Zhu L., Kielland V., Straathof A.J.J., and Jongejan J.A. Simple dissolution-reaction model for enzymatic conversion of suspension of solid substrate. Biotechnol Bioeng 56 (1997) 433-440
    • (1997) Biotechnol Bioeng , vol.56 , pp. 433-440
    • Wolff, A.1    Zhu, L.2    Kielland, V.3    Straathof, A.J.J.4    Jongejan, J.A.5
  • 28
    • 0029636165 scopus 로고
    • Enzyme catalyzed biotransformation in aqueous two-phase system with precipitated substrate and/or product
    • Kasche V., and Galunsky B. Enzyme catalyzed biotransformation in aqueous two-phase system with precipitated substrate and/or product. Biotechnol Bioeng 45 (1995) 261-267
    • (1995) Biotechnol Bioeng , vol.45 , pp. 261-267
    • Kasche, V.1    Galunsky, B.2
  • 29
    • 0034597428 scopus 로고    scopus 로고
    • Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester
    • Liu Y.-Y., Xu J.-H., and Hu Y. Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester. J Mol Cat B Enz 10 (2000) 523-529
    • (2000) J Mol Cat B Enz , vol.10 , pp. 523-529
    • Liu, Y.-Y.1    Xu, J.-H.2    Hu, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.