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Volumn 31, Issue 5, 2002, Pages 609-614

Total enzymatic resolution of racemic 2-(4-methoxybenzyl)-1-cyclohexanols and 2-(4-methoxybenzyl)-1-cyclopentanols

Author keywords

Acyl donor; Candida antarctica; Enantioselectivity; Temperature; Water activity

Indexed keywords

CATALYSIS; ORGANIC COMPOUNDS; SUBSTRATES; THERMAL EFFECTS;

EID: 0037015418     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(02)00144-8     Document Type: Article
Times cited : (9)

References (20)
  • 1
    • 0030965976 scopus 로고    scopus 로고
    • A series of bicyclic insect juvenile hormone analogs of Czech origin: Twenty years of development
    • Wimmer Z., Rejzek M., Zarevucka M., Kuldova J., Hrdy I., Nemec V.et al. A series of bicyclic insect juvenile hormone analogs of Czech origin: twenty years of development. J. Chem. Ecol. 23(3):1997;605-628.
    • (1997) J. Chem. Ecol. , vol.23 , Issue.3 , pp. 605-628
    • Wimmer, Z.1    Rejzek, M.2    Zarevucka, M.3    Kuldova, J.4    Hrdy, I.5    Nemec, V.6
  • 2
    • 0032819115 scopus 로고    scopus 로고
    • Lipase B from Candida antarctica catalyses enantioselective transesterification of 2-(4-methoxybenzyl)-1-cyclohexanols and 2-(4-methoxybenzyl)-1-cyclopentanols
    • Brunet C., Zarevucka M., Wimmer Z., Lipase B. Lipase B from Candida antarctica catalyses enantioselective transesterification of 2-(4-methoxybenzyl)-1-cyclohexanols and 2-(4-methoxybenzyl)-1-cyclopentanols. Biotechnol. Lett. 21:1999;605-610.
    • (1999) Biotechnol. Lett. , vol.21 , pp. 605-610
    • Brunet, C.1    Zarevucka, M.2    Wimmer, Z.3    Lipase, B.4
  • 3
    • 0027990305 scopus 로고
    • High enantioselective esterification of 2-aryl propionic acids catalyzed by immobilized lipase from Candida antarctica: A mechanistic approach
    • Arroyo M., Sinisterra J.V. High enantioselective esterification of 2-aryl propionic acids catalyzed by immobilized lipase from Candida antarctica: a mechanistic approach. J. Org. Chem. 59:1994;4410-4417.
    • (1994) J. Org. Chem. , vol.59 , pp. 4410-4417
    • Arroyo, M.1    Sinisterra, J.V.2
  • 4
    • 0031858561 scopus 로고    scopus 로고
    • Lipase-catalysed acetylation of 3-substituted 2,3-dihydro-1H-1,4-benzodiazepin-2-ones: Effect of temperature and conformation on enantioselectivity and configuration,
    • Avdagic A., Lesac A., Majer Z., Hollosi M., Sunjic V. Lipase-catalysed acetylation of 3-substituted 2,3-dihydro-1H-1,4-benzodiazepin-2-ones: Effect of temperature and conformation on enantioselectivity and configuration, Helv. Chim. Acta. 81:1998;1567-1582.
    • (1998) Helv. Chim. Acta , vol.81 , pp. 1567-1582
    • Avdagic, A.1    Lesac, A.2    Majer, Z.3    Hollosi, M.4    Sunjic, V.5
  • 5
    • 0026462672 scopus 로고
    • Lipase-catalysed transesterification using 2,2,2-trifluoroethylbutyrate: Effect of temperature on rate of reaction and enantioselectivity
    • Parmar V.S., Prasad A.K., Singh P.K., Gupta S. Lipase-catalysed transesterification using 2,2,2-trifluoroethylbutyrate: effect of temperature on rate of reaction and enantioselectivity. Tetrahedron: Asymmetry. 3(11):1992;1395-1398.
    • (1992) Tetrahedron: Asymmetry , vol.3 , Issue.11 , pp. 1395-1398
    • Parmar, V.S.1    Prasad, A.K.2    Singh, P.K.3    Gupta, S.4
  • 6
    • 0031126436 scopus 로고    scopus 로고
    • High temperature-induced high enantioselectivity of lipase for esterifications of 2-phenoxypropionic acids in organic solvent
    • Yasufuku Y., Ueji S. High temperature-induced high enantioselectivity of lipase for esterifications of 2-phenoxypropionic acids in organic solvent. Bioorg. Chem. 25:1997;88-99.
    • (1997) Bioorg. Chem. , vol.25 , pp. 88-99
    • Yasufuku, Y.1    Ueji, S.2
  • 7
    • 0033586945 scopus 로고    scopus 로고
    • Influence of water activity on the enantioselective esterification of (R, S)-ibuprofen by Candida antarctica lipase B in solventless media
    • Pepin P., Lortie R. Influence of water activity on the enantioselective esterification of (R, S)-ibuprofen by Candida antarctica lipase B in solventless media. Biotechnol. Bioeng. 63(4):1999;502-505.
    • (1999) Biotechnol. Bioeng. , vol.63 , Issue.4 , pp. 502-505
    • Pepin, P.1    Lortie, R.2
  • 8
    • 0027527221 scopus 로고
    • Water activity influences enantioselectivity in a lipase-catalysed resolution by esterification in organic solvents
    • Hogberg H.-E., Edlund H., Berglund P., Hedenström H. Water activity influences enantioselectivity in a lipase-catalysed resolution by esterification in organic solvents. Tetrahedron: Asymmetry. 4(10):1993;2123-2126.
    • (1993) Tetrahedron: Asymmetry , vol.4 , Issue.10 , pp. 2123-2126
    • Hogberg, H.-E.1    Edlund, H.2    Berglund, P.3    Hedenström, H.4
  • 9
    • 0027483513 scopus 로고
    • Water activity does not influence the enantioselectivity of lipase PS and lipoprotein lipase in organic solvents
    • Bovara R., Carrea G., Ottalina G., Riva S. Water activity does not influence the enantioselectivity of lipase PS and lipoprotein lipase in organic solvents. Biotechnol. Lett. 15(2):1993;169-174.
    • (1993) Biotechnol. Lett. , vol.15 , Issue.2 , pp. 169-174
    • Bovara, R.1    Carrea, G.2    Ottalina, G.3    Riva, S.4
  • 10
    • 84990106353 scopus 로고
    • Optimisation of enantioselective biocatalysis in organic solvents: The use of lipases
    • Chen C-S., Sih C.-J. optimisation of enantioselective biocatalysis in organic solvents: the use of lipases. Angew. Chem. Int. Ed. Engl. 28:1989;695-707.
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 695-707
    • Chen, C.-S.1    Sih, C.-J.2
  • 11
    • 0026592262 scopus 로고
    • Effects of medium and of reaction conditions on the enantioselectivity of lipases in organic solvents and possible rationales
    • Secundo F., Riva S., Carrea G. Effects of medium and of reaction conditions on the enantioselectivity of lipases in organic solvents and possible rationales. Tetrahedron: Asymmetry. 3(2):1992;267-280.
    • (1992) Tetrahedron: Asymmetry , vol.3 , Issue.2 , pp. 267-280
    • Secundo, F.1    Riva, S.2    Carrea, G.3
  • 12
    • 0029915768 scopus 로고    scopus 로고
    • Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications
    • Ema T., Maeno S., Takaya Y., Sakai T., Utaka M. Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications. Tetrahedron: Asymmetry. 7(3):1996;625-628.
    • (1996) Tetrahedron: Asymmetry , vol.7 , Issue.3 , pp. 625-628
    • Ema, T.1    Maeno, S.2    Takaya, Y.3    Sakai, T.4    Utaka, M.5
  • 13
    • 0031455616 scopus 로고    scopus 로고
    • The enantiomeric ratio: Origin, determination and prediction
    • Straathof A.J.J., Jongejean J.A. The enantiomeric ratio: origin, determination and prediction. Enzyme Microb. Technol. 21:1997;559-571.
    • (1997) Enzyme Microb. Technol. , vol.21 , pp. 559-571
    • Straathof, A.J.J.1    Jongejean, J.A.2
  • 14
    • 0028360990 scopus 로고
    • Some aspects of biocatalysis in organic solvents
    • Kvittingen L. Some aspects of biocatalysis in organic solvents. Tetrahedron. 50(28):1994;8253-8274.
    • (1994) Tetrahedron , vol.50 , Issue.28 , pp. 8253-8274
    • Kvittingen, L.1
  • 15
    • 0028773288 scopus 로고
    • The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica
    • Uppenberg J., Hansen M.T., Patkar S., Jones T.A. The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica. Structure. 2:1994;293-308.
    • (1994) Structure , vol.2 , pp. 293-308
    • Uppenberg, J.1    Hansen, M.T.2    Patkar, S.3    Jones, T.A.4
  • 16
    • 0029592705 scopus 로고
    • The Candida antarctica lipase B catalysed kinetic resolution of Seudonol in non-aqueous media of controlled water activity
    • Orrenius C., Norin T., Hult K., Carrea G. The Candida antarctica lipase B catalysed kinetic resolution of Seudonol in non-aqueous media of controlled water activity. Tetrahedron: Asymmetry. 6(12):1995;3023-3030.
    • (1995) Tetrahedron: Asymmetry , vol.6 , Issue.12 , pp. 3023-3030
    • Orrenius, C.1    Norin, T.2    Hult, K.3    Carrea, G.4
  • 18
    • 0027492918 scopus 로고
    • Enzymatic resolution of butanoic esters of 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and 1-[2-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol
    • Waagen V., Hollingsaeter I., Partali V., Thorstad O., Anthonsen T. Enzymatic resolution of butanoic esters of 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and 1-[2-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol. Tetrahedron: Asymmetry. 4(10):1993;2265-2274.
    • (1993) Tetrahedron: Asymmetry , vol.4 , Issue.10 , pp. 2265-2274
    • Waagen, V.1    Hollingsaeter, I.2    Partali, V.3    Thorstad, O.4    Anthonsen, T.5
  • 19
    • 0029417196 scopus 로고
    • Crystallographic and molecular modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols
    • Uppenberg J., Orhner N., Norin M., Hult K., Kleywegt G.J., Patkar S.et al. Crystallographic and molecular modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry. 34:1995;16838-16851.
    • (1995) Biochemistry , vol.34 , pp. 16838-16851
    • Uppenberg, J.1    Orhner, N.2    Norin, M.3    Hult, K.4    Kleywegt, G.J.5    Patkar, S.6
  • 20
    • 0002824072 scopus 로고
    • Sih and Wu Resolution of enantiomers via biocatalysis
    • Sih and Wu Resolution of enantiomers via biocatalysis. Top Stereochem 1989;19:63-125.
    • (1989) Top Stereochem , vol.19 , pp. 63-125


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