메뉴 건너뛰기




Volumn 45, Issue 6, 2010, Pages 859-865

Lipase-catalyzed kinetic resolution of 2-methylene-substituted cycloalkanols in batch and continuous-flow modes

Author keywords

Acylation; Biotransformations; Continuous flow enzyme reactor; Cycloalkanol; Enantioselectivity; Enzyme catalysis

Indexed keywords

2-METHYLENE; BATCH MODES; CANDIDA ANTARCTICA LIPASE B; CONTINUOUS MODE; CONTINUOUS-FLOW; CONTINUOUS-FLOW ENZYME REACTOR; EFFECT OF TEMPERATURE; ENZYME CATALYSIS; ENZYME REACTORS; KINETIC RESOLUTION; PSEUDOMONAS FLUORESCENS; RACEMIC SECONDARY ALCOHOLS; SHAKE FLASKS; VINYL ACETATES;

EID: 77951022179     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2010.02.006     Document Type: Article
Times cited : (39)

References (34)
  • 3
    • 0033179762 scopus 로고    scopus 로고
    • Continuous enzymatic transesterification of high oleic sunflower oil in a packed bed reactor: influence of the glycerol production
    • Dossat V., Combes D., and Marty A. Continuous enzymatic transesterification of high oleic sunflower oil in a packed bed reactor: influence of the glycerol production. Enzyme Microb Technol 25 (1999) 194-200
    • (1999) Enzyme Microb Technol , vol.25 , pp. 194-200
    • Dossat, V.1    Combes, D.2    Marty, A.3
  • 5
    • 10844227997 scopus 로고    scopus 로고
    • Application of lipases in kinetic resolution of racemates
    • Ghanem A., and Aboul-Enein H.Y. Application of lipases in kinetic resolution of racemates. Chirality 17 (2005) 1-15
    • (2005) Chirality , vol.17 , pp. 1-15
    • Ghanem, A.1    Aboul-Enein, H.Y.2
  • 6
    • 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
  • 7
    • 34548807521 scopus 로고    scopus 로고
    • Convergency and divergency as strategic elements in total synthesis: the total synthesis of (-)-drupacine and the formal total synthesis of (±)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine
    • Liu Q., Ferreira E.M., and Stolz B.M. Convergency and divergency as strategic elements in total synthesis: the total synthesis of (-)-drupacine and the formal total synthesis of (±)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine. J Org Chem 72 (2007) 7352-7358
    • (2007) J Org Chem , vol.72 , pp. 7352-7358
    • Liu, Q.1    Ferreira, E.M.2    Stolz, B.M.3
  • 8
    • 0043201033 scopus 로고    scopus 로고
    • 3-promoted eliminative ring-opening of β-hydroxy epoxides: highly stereoselective synthesis of terminal α-hydroxy olefins
    • 3-promoted eliminative ring-opening of β-hydroxy epoxides: highly stereoselective synthesis of terminal α-hydroxy olefins. Tetrahedron: Asymmetry 14 (2003) 2189-2193
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2189-2193
    • Wang, F.W.1    Wang, S.H.2    Tu, Q.Y.3    Ren, S.K.4
  • 9
    • 0000622597 scopus 로고    scopus 로고
    • Novel conversion of 1,2-disubstituted cis-epoxides to one-carbon homologated allylic alcohols using dimethylsulfonium methylide
    • Alcaraz L., Cridland A., and Kinchin E. Novel conversion of 1,2-disubstituted cis-epoxides to one-carbon homologated allylic alcohols using dimethylsulfonium methylide. Org Lett 3 (2001) 4051-4053
    • (2001) Org Lett , vol.3 , pp. 4051-4053
    • Alcaraz, L.1    Cridland, A.2    Kinchin, E.3
  • 10
    • 0000783681 scopus 로고    scopus 로고
    • A stereochemical study of the isomerization of cyclopropyl ethers to allyl ethers catalyzed with zinc iodide
    • Sugimura T., Futagawa T., Mori A., Ryu I., Sonoda N., and Tai A. A stereochemical study of the isomerization of cyclopropyl ethers to allyl ethers catalyzed with zinc iodide. J Org Chem 61 (1996) 6100-6103
    • (1996) J Org Chem , vol.61 , pp. 6100-6103
    • Sugimura, T.1    Futagawa, T.2    Mori, A.3    Ryu, I.4    Sonoda, N.5    Tai, A.6
  • 11
    • 30944467969 scopus 로고    scopus 로고
    • Enantioselective synthesis of vicinal halohydrins via dynamic kinetic resolution
    • Ros A., Magriz A., Dietrich H., Fernández R., Alvarez E., and Lassaletta J.M. Enantioselective synthesis of vicinal halohydrins via dynamic kinetic resolution. Org Lett 8 (2006) 127-130
    • (2006) Org Lett , vol.8 , pp. 127-130
    • Ros, A.1    Magriz, A.2    Dietrich, H.3    Fernández, R.4    Alvarez, E.5    Lassaletta, J.M.6
  • 13
    • 0042331931 scopus 로고    scopus 로고
    • Kinetic resolution of trans-2-acetoxycycloalkan-1-ols by lipase-catalysed enantiomerically selective acylation
    • Bódai V., Orovecz O., Szakács Gy, Novák L., and Poppe L. Kinetic resolution of trans-2-acetoxycycloalkan-1-ols by lipase-catalysed enantiomerically selective acylation. Tetrahedron: Asymmetry 14 (2003) 2605-2612
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2605-2612
    • Bódai, V.1    Orovecz, O.2    Szakács Gy3    Novák, L.4    Poppe, L.5
  • 14
    • 0027370104 scopus 로고
    • Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification
    • Fukazawa T., and Hashimoto T. Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification. Tetrahedron: Asymmetry 4 (1993) 2323-2326
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2323-2326
    • Fukazawa, T.1    Hashimoto, T.2
  • 15
    • 0025609890 scopus 로고
    • A general method for separation of enantiomeric trans-2-substituted cyclohexanols
    • Hönig H., and Seufer-Wasserthal P. A general method for separation of enantiomeric trans-2-substituted cyclohexanols. Synthesis 12 (1990) 1137-1140
    • (1990) Synthesis , vol.12 , pp. 1137-1140
    • Hönig, H.1    Seufer-Wasserthal, P.2
  • 16
    • 0027196612 scopus 로고
    • Substrate modification to increase the enantioselectivity of hydrolases. A route to optically-active cyclic allylic alcohols
    • Gupta A.K., and Kazlauskas R.J. Substrate modification to increase the enantioselectivity of hydrolases. A route to optically-active cyclic allylic alcohols. Tetrahedron: Asymmetry 4 (1993) 879-888
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 879-888
    • Gupta, A.K.1    Kazlauskas, R.J.2
  • 17
    • 0242290842 scopus 로고    scopus 로고
    • Enantioseparation of chiral alcohols by complex formation and subsequent supercritical fluid extraction
    • Székely E., Simándi B., Fogassy E., Kemény S., and Kmecz I. Enantioseparation of chiral alcohols by complex formation and subsequent supercritical fluid extraction. Chirality 15 (2003) 783-786
    • (2003) Chirality , vol.15 , pp. 783-786
    • Székely, E.1    Simándi, B.2    Fogassy, E.3    Kemény, S.4    Kmecz, I.5
  • 18
    • 0345732180 scopus 로고    scopus 로고
    • Continuous flow techniques in organic synthesis
    • Jas G., and Kirchning A. Continuous flow techniques in organic synthesis. Chem Eur J 9 (2003) 5708-5723
    • (2003) Chem Eur J , vol.9 , pp. 5708-5723
    • Jas, G.1    Kirchning, A.2
  • 19
    • 33747189999 scopus 로고    scopus 로고
    • Combining enabling techniques in organic synthesis: continuous flow processes with heterogenized catalysts
    • Kirchning A., Solodenko W., and Mennecke K. Combining enabling techniques in organic synthesis: continuous flow processes with heterogenized catalysts. Chem Eur J 12 (2006) 5972-5990
    • (2006) Chem Eur J , vol.12 , pp. 5972-5990
    • Kirchning, A.1    Solodenko, W.2    Mennecke, K.3
  • 20
    • 0030289144 scopus 로고    scopus 로고
    • Biocatalytic synthesis of some chiral pharmaceutical intermediates by lipases
    • Patel R.N., Banerjee A., and Szarka L.J. Biocatalytic synthesis of some chiral pharmaceutical intermediates by lipases. J Am Oil Chem Soc 73 (1996) 1363-1375
    • (1996) J Am Oil Chem Soc , vol.73 , pp. 1363-1375
    • Patel, R.N.1    Banerjee, A.2    Szarka, L.J.3
  • 21
    • 0034521368 scopus 로고    scopus 로고
    • Enantioselective synthesis of (S)-ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on Accurel MP1000
    • Chen J.C., and Tsai S.W. Enantioselective synthesis of (S)-ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on Accurel MP1000. Biotechnol Prog 16 (2000) 986-992
    • (2000) Biotechnol Prog , vol.16 , pp. 986-992
    • Chen, J.C.1    Tsai, S.W.2
  • 22
    • 0038274857 scopus 로고    scopus 로고
    • The kinetic resolution of 2-(4-chlorophenoxy) propionic acid using Candida rugosa lipase
    • Ujang Z., Husain W.H., Seng M.C., and Rashid A.H.A. The kinetic resolution of 2-(4-chlorophenoxy) propionic acid using Candida rugosa lipase. Process Biochem 38 (2003) 1483-1488
    • (2003) Process Biochem , vol.38 , pp. 1483-1488
    • Ujang, Z.1    Husain, W.H.2    Seng, M.C.3    Rashid, A.H.A.4
  • 24
    • 38949172001 scopus 로고    scopus 로고
    • Enantiomer selective acylation of racemic alcohols by lipases in continuous-flow bioreactors
    • Csajági Cs, Szatzker G., To{combining double acute accent}ke E.R., Ürge L., Davas F., and Poppe L. Enantiomer selective acylation of racemic alcohols by lipases in continuous-flow bioreactors. Tetrahedron: Asymmetry 19 (2008) 237-246
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 237-246
    • Csajági Cs1    Szatzker, G.2    Toke, E.R.3    Ürge, L.4    Davas, F.5    Poppe, L.6
  • 25
    • 33947454963 scopus 로고
    • Reduction of some enolizable β-dicarbonyl compounds to unsaturated alcohols by lithium aluminum hydride. I. Monocyclic β-ketoesters and α-hydroxymethylene ketones
    • Dreiding A.S., and Hartman J. Reduction of some enolizable β-dicarbonyl compounds to unsaturated alcohols by lithium aluminum hydride. I. Monocyclic β-ketoesters and α-hydroxymethylene ketones. J Am Chem Soc 75 (1953) 939-943
    • (1953) J Am Chem Soc , vol.75 , pp. 939-943
    • Dreiding, A.S.1    Hartman, J.2
  • 26
    • 0009994352 scopus 로고
    • Cyclic dienes. XVII. 3-Methylenecyclohexene
    • Bailey W.J., and Goossens J.C. Cyclic dienes. XVII. 3-Methylenecyclohexene. J Am Chem Soc 78 (1956) 2804-2806
    • (1956) J Am Chem Soc , vol.78 , pp. 2804-2806
    • Bailey, W.J.1    Goossens, J.C.2
  • 27
    • 33845278418 scopus 로고
    • Enantioselective ring cleavage of meso-epoxides with B-halodiisopinocampheylboranes
    • Joshi N.N., Srebnik M., and Brown H.C. Enantioselective ring cleavage of meso-epoxides with B-halodiisopinocampheylboranes. J Am Chem Soc 110 (1988) 6246-6248
    • (1988) J Am Chem Soc , vol.110 , pp. 6246-6248
    • Joshi, N.N.1    Srebnik, M.2    Brown, H.C.3
  • 28
    • 0041390375 scopus 로고    scopus 로고
    • Novel hydrolases from thermophilic filamentous fungi for enantiomerically and enantiotopically selective biotransformations
    • Bódai V., Peredi R., Bálint J., Egri G., Novák L., Szakács G., et al. Novel hydrolases from thermophilic filamentous fungi for enantiomerically and enantiotopically selective biotransformations. Adv Synth Catal 345 (2003) 811-818
    • (2003) Adv Synth Catal , vol.345 , pp. 811-818
    • Bódai, V.1    Peredi, R.2    Bálint, J.3    Egri, G.4    Novák, L.5    Szakács, G.6
  • 29
    • 77951024185 scopus 로고    scopus 로고
    • Optical resolution of 2-pentanol and 2-hexanol transesterification reactions catalysed by Burkholderia cepacia (PS) lipase
    • Paska O., Zarcula C., and Peter F. Optical resolution of 2-pentanol and 2-hexanol transesterification reactions catalysed by Burkholderia cepacia (PS) lipase. Ann West Univ Timisoara Ser Chem 16 (2007) 73-78
    • (2007) Ann West Univ Timisoara Ser Chem , vol.16 , pp. 73-78
    • Paska, O.1    Zarcula, C.2    Peter, F.3
  • 30
    • 33744458694 scopus 로고    scopus 로고
    • Kinetic resolutions with novel, highly enantioselective fungal lipases produced by solid state fermentation
    • Nagy V., To{combining double acute accent}ke E.R., Chee Keong L., Szatzker G., Ibrahim D., Che-Omar I., et al. Kinetic resolutions with novel, highly enantioselective fungal lipases produced by solid state fermentation. J Mol Catal B: Enzym 39 (2006) 141-148
    • (2006) J Mol Catal B: Enzym , vol.39 , pp. 141-148
    • Nagy, V.1    Toke, E.R.2    Chee Keong, L.3    Szatzker, G.4    Ibrahim, D.5    Che-Omar, I.6
  • 31
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen C.S., Fujimoto Y., Girdaukas G., and Sih C.J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104 (1982) 7294-7299
    • (1982) J Am Chem Soc , vol.104 , pp. 7294-7299
    • Chen, C.S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 32
    • 0027897680 scopus 로고
    • A simple method to determine the enantiomeric ratio in enantioselective biocatalysis
    • Rakels J.L.L., Straathof A.J.J., and Heijnen J.J. A simple method to determine the enantiomeric ratio in enantioselective biocatalysis. Enzyme Microb Technol 15 (1993) 1051-1056
    • (1993) Enzyme Microb Technol , vol.15 , pp. 1051-1056
    • Rakels, J.L.L.1    Straathof, A.J.J.2    Heijnen, J.J.3
  • 33
    • 1542795792 scopus 로고
    • Stereochemistry of a [2,3] sigmatropic allyl-sulfoxide/allyl sulfenate rearrangement
    • Hoffmann R.W., Gerlach R., and Goldmann S. Stereochemistry of a [2,3] sigmatropic allyl-sulfoxide/allyl sulfenate rearrangement. Tetrahedron Lett 19 (1978) 2599-2602
    • (1978) Tetrahedron Lett , vol.19 , pp. 2599-2602
    • Hoffmann, R.W.1    Gerlach, R.2    Goldmann, S.3
  • 34
    • 33751499686 scopus 로고
    • A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed 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 catalyzed 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.