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Volumn 19, Issue 5, 1996, Pages 361-366

Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol

Author keywords

Enantiospecificity; Lipase; Steapsin; Tetrahydropyran 2 methanol

Indexed keywords

BIOSYNTHESIS; ENZYMES; ESTERIFICATION; FRACTIONATION; HYDROLYSIS; OPTIMIZATION; SCREENING;

EID: 0030271206     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(96)00029-4     Document Type: Article
Times cited : (9)

References (31)
  • 3
    • 15844366864 scopus 로고
    • Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products
    • 3. Boivin, T. L. B. Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products. Tetrahedron 1987, 43, 3309-3362
    • (1987) Tetrahedron , vol.43 , pp. 3309-3362
    • Boivin, T.L.B.1
  • 4
    • 0002939651 scopus 로고
    • Enolate Claisen rearrangement of esters from furanoid pyranoid glycals
    • 4. Ireland, R. E., Thaisrivongs, S., Vanier, N., and Wilcox, C. S. Enolate Claisen rearrangement of esters from furanoid pyranoid glycals. J. Org. Chem. 1980, 45, 48-61
    • (1980) J. Org. Chem. , vol.45 , pp. 48-61
    • Ireland, R.E.1    Thaisrivongs, S.2    Vanier, N.3    Wilcox, C.S.4
  • 5
    • 60349131073 scopus 로고
    • Saluretic sulfonamides
    • Brit. Patent No. 1,031,916
    • 5. Horstman, H., Wollweber, H., and Meng, K. Saluretic sulfonamides. Brit. Patent No. 1,031,916. Chem. Abstr, 1969, 70, 19915u
    • (1969) Chem. Abstr , vol.70
    • Horstman, H.1    Wollweber, H.2    Meng, K.3
  • 6
    • 85030271704 scopus 로고
    • 4-Chloro-or 4-bromo-5-sulfamyl-N-substituted anthranilic acid diuretic compounds
    • U.S. Patent No. 3,577,409
    • 6. Cragoe Jr., E. J. 4-Chloro-or 4-bromo-5-sulfamyl-N-substituted anthranilic acid diuretic compounds. U.S. Patent No. 3,577,409. Chem. Abstr. 1971, 75, 35739y
    • (1971) Chem. Abstr. , vol.75
    • Cragoe E.J., Jr.1
  • 7
    • 0018603812 scopus 로고
    • N-[(Tetrahydrofurfuryl)alkyl] and N-(alkoxyalkyl) derivatives of (-)-normetazocine - Compounds with differentiated opioid action profiles
    • 7. Merz, H. and Stockhaus, K. N-[(Tetrahydrofurfuryl)alkyl] and N-(alkoxyalkyl) derivatives of (-)-normetazocine - compounds with differentiated opioid action profiles. J. Med. Chem. 1979, 22, 1475-1483
    • (1979) J. Med. Chem. , vol.22 , pp. 1475-1483
    • Merz, H.1    Stockhaus, K.2
  • 8
    • 0037529671 scopus 로고    scopus 로고
    • III-induced addition of tetrahydrofurfuryl alcohol, telrahydropyran-2-methanol, D-gluconate, methanol and ethanol to maleate
    • In press
    • III-induced addition of tetrahydrofurfuryl alcohol, telrahydropyran-2-methanol, D-gluconate, methanol and ethanol to maleate. Acta Chem. Scand. 1996, 50, In press
    • (1996) Acta Chem. Scand. , pp. 50
    • Quartey, E.G.K.1    Peters, J.A.2    Van Bekkum, H.3    Anthonsen, T.4
  • 9
    • 37049084487 scopus 로고
    • Multinuclear magnetic resonance study of the complexation of lanthanide(III) cations with tetrahydropvran-2-methanol
    • 9. Quartey, E. G. K., van Bekkum, H., and Peters, J. A. Multinuclear magnetic resonance study of the complexation of lanthanide(III) cations with tetrahydropvran-2-methanol. J. Chem. Soc., Dalton Trans. 1992, 1139-1143
    • (1992) J. Chem. Soc., Dalton Trans. , pp. 1139-1143
    • Quartey, E.G.K.1    Van Bekkum, H.2    Peters, J.A.3
  • 10
    • 33845470686 scopus 로고
    • Lipase-catalyzed hydrolysis as a route to esters of chiral epoxy alcohols
    • 10. Lander, W. E. and Whitesides, G. M. Lipase-catalyzed hydrolysis as a route to esters of chiral epoxy alcohols. J. Am. Chem. Soc. 1984, 106, 7250-7251
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7250-7251
    • Lander, W.E.1    Whitesides, G.M.2
  • 11
    • 0027138526 scopus 로고
    • Selectivity-enhancement of hydrolase reactions
    • 11. Faber, K., Ottolina, G., and Riva, S. Selectivity-enhancement of hydrolase reactions. Biocatalysis 1993, 8, 91-132
    • (1993) Biocatalysis , vol.8 , pp. 91-132
    • Faber, K.1    Ottolina, G.2    Riva, S.3
  • 12
    • 0001510557 scopus 로고
    • Applications of empirical rules for optical rotation to problems of conformational analysis
    • 12. Lemieux, R. U. and Martin, J. C. Applications of empirical rules for optical rotation to problems of conformational analysis. Carbohydr. Res. 1970, 13, 139-161
    • (1970) Carbohydr. Res. , vol.13 , pp. 139-161
    • Lemieux, R.U.1    Martin, J.C.2
  • 13
    • 20644469267 scopus 로고
    • Quantitative analysis of biochemical kinetic resolutions of enantiomers
    • 13. Chen, C.-S., Fujimoto, Y., Girdaukas, G., and Sih, C. J. Quantitative analysis of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 1982, 104, 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
  • 14
    • 0026221188 scopus 로고
    • Enzymatic resolution of (5)-(+)-Naproxen in a continuous reactor
    • 14. Battistel, E., Bianchi, D., Cesti, P., and Pina, C. Enzymatic resolution of (5)-(+)-Naproxen in a continuous reactor. Biotechnol. Bioeng. 1991, 38, 659-664
    • (1991) Biotechnol. Bioeng. , vol.38 , pp. 659-664
    • Battistel, E.1    Bianchi, D.2    Cesti, P.3    Pina, C.4
  • 15
    • 0018130466 scopus 로고
    • Purification of pancreatic lipase via its affinity for bile salts and apolar surfaces
    • 15. Momsen, W. E. and Brockman, H. L. Purification of pancreatic lipase via its affinity for bile salts and apolar surfaces. J. Lipid Res. 1978, 19, 1032-1037
    • (1978) J. Lipid Res. , vol.19 , pp. 1032-1037
    • Momsen, W.E.1    Brockman, H.L.2
  • 16
    • 0017133074 scopus 로고
    • On the binding of bile salt to pancreatic lipase
    • 16. Borgstrøm, B. and Donnér, J. On the binding of bile salt to pancreatic lipase. Biochim. Biophys. Acta 1976, 450, 352-357
    • (1976) Biochim. Biophys. Acta , vol.450 , pp. 352-357
    • Borgstrøm, B.1    Donnér, J.2
  • 17
    • 0015837841 scopus 로고
    • Pancreatic lipase and colipase: Interactions and effects of bile salts and other detergents
    • 17. Borgstrøm, B. and Erlandson, C. Pancreatic lipase and colipase: Interactions and effects of bile salts and other detergents. Eur. J. Biochem. 1973, 37, 60-68
    • (1973) Eur. J. Biochem. , vol.37 , pp. 60-68
    • Borgstrøm, B.1    Erlandson, C.2
  • 18
    • 33751155794 scopus 로고
    • A 2-propanol treatment increases the enantioselectivity of Candida rugosa lipase toward esters of chiral carboxylic acids
    • 18. Colton, I. J., Ahmed, S. H., and Kazlauskas, R. J. A 2-propanol treatment increases the enantioselectivity of Candida rugosa lipase toward esters of chiral carboxylic acids. J. Org. Chem. 1995, 60, 212-217
    • (1995) J. Org. Chem. , vol.60 , pp. 212-217
    • Colton, I.J.1    Ahmed, S.H.2    Kazlauskas, R.J.3
  • 19
    • 0002517288 scopus 로고
    • Lipase-catalyzed resolution of isopropylidene glycerol: Effect of cosolvents on enantioselectivity
    • 19. Bosetti, A., Bianchi, D., Cesti, P., and Golini, P. Lipase-catalyzed resolution of isopropylidene glycerol: Effect of cosolvents on enantioselectivity. Biocatalysis 1994, 9, 71-79
    • (1994) Biocatalysis , vol.9 , pp. 71-79
    • Bosetti, A.1    Bianchi, D.2    Cesti, P.3    Golini, P.4
  • 20
    • 5844252510 scopus 로고
    • Solvatochromic dyes as solvent polarity indicators
    • 20. Reichardt, C. Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94, 2319-2358
    • (1994) Chem. Rev. , vol.94 , pp. 2319-2358
    • Reichardt, C.1
  • 21
    • 0001201991 scopus 로고
    • The effectivity of solvents as electron pair donors
    • 21. Marcus, Y. The effectivity of solvents as electron pair donors. J. Sol. Chem. 1984, 13, 599-624
    • (1984) J. Sol. Chem. , vol.13 , pp. 599-624
    • Marcus, Y.1
  • 22
    • 0022612265 scopus 로고
    • The effect of dimethyl sulfoxide on the enantioselectivity in the pig liver esterase-catalyzed hydrolysis of dialkylated propanedioic acid dimethyl esters
    • 22. Bjørkling, F., Boutelje, J., Gatenbeck, S., Hult, K., Norin, T., and Szmulik, P. The effect of dimethyl sulfoxide on the enantioselectivity in the pig liver esterase-catalyzed hydrolysis of dialkylated propanedioic acid dimethyl esters. Bioorg. Chem. 1986, 14, 176-181
    • (1986) Bioorg. Chem. , vol.14 , pp. 176-181
    • Bjørkling, F.1    Boutelje, J.2    Gatenbeck, S.3    Hult, K.4    Norin, T.5    Szmulik, P.6
  • 23
    • 0000297996 scopus 로고
    • Enzymes in asymmetric synthesis: Effect of reaction media on the PLE-catalyzed hydrolysis of diesters
    • 23. Guanti, G., Banfi, L., Narisano, E., Riva, R., and Thea, S. Enzymes in asymmetric synthesis: Effect of reaction media on the PLE-catalyzed hydrolysis of diesters. Tetrahedron Lett. 1986, 27, 4639-4642
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4639-4642
    • Guanti, G.1    Banfi, L.2    Narisano, E.3    Riva, R.4    Thea, S.5
  • 24
    • 0000245372 scopus 로고
    • Effects of organic cosolvents on enzyme stereospecificity. The enantiomeric specificity of α-chymotrypsin is reduced by high organic solvent concentrations
    • 24. Jones, J. B. and Mehes, M. M. Effects of organic cosolvents on enzyme stereospecificity. The enantiomeric specificity of α-chymotrypsin is reduced by high organic solvent concentrations. Can. J. Chem. 1979, 57, 2245-2248
    • (1979) Can. J. Chem. , vol.57 , pp. 2245-2248
    • Jones, J.B.1    Mehes, M.M.2
  • 25
    • 0026592262 scopus 로고
    • Effects of medium and of reaction conditions on the enantioselectivity of lipases in organic solvents and possible rationales
    • 25. Secundo, F., Riva, S., and Carrea, G. Effects of medium and of reaction conditions on the enantioselectivity of lipases in organic solvents and possible rationales. Tetrahedron: Asymmetry 1992, 3, 267-280
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 267-280
    • Secundo, F.1    Riva, S.2    Carrea, G.3
  • 26
    • 0028855057 scopus 로고
    • The role of solvents in the control of enzyme selectivity in organic media
    • 26. Carrea, G., Ottolina, G., and Riva, S. The role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol. 1995, 13, 63-70
    • (1995) Trends Biotechnol. , vol.13 , pp. 63-70
    • Carrea, G.1    Ottolina, G.2    Riva, S.3
  • 27
    • 0000344071 scopus 로고
    • Synthesis of both enantiomeric forms of 2-substituted 1,3-propanediol monoacetates starting from a common prochiral precursor using enzymatic transformation in aqueous and organic media
    • 27. Ramos Tombo, G. M., Schär, H.-P., Fernandez i Busquets, X., and Ghisalba, O. Synthesis of both enantiomeric forms of 2-substituted 1,3-propanediol monoacetates starting from a common prochiral precursor using enzymatic transformation in aqueous and organic media. Tetrahedron Lett. 1986, 27, 5707-5710
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5707-5710
    • Ramos Tombo, G.M.1    Schär, H.-P.2    Fernandez Busquets, X.I.3    Ghisalba, O.4
  • 28
    • 0020725090 scopus 로고
    • Determination of lipase specificity
    • 28. Jensen, R. G., Dejong, F. A., and Clark, R. M. Determination of lipase specificity. Lipids 1983, 18, 239-252
    • (1983) Lipids , vol.18 , pp. 239-252
    • Jensen, R.G.1    Dejong, F.A.2    Clark, R.M.3
  • 29
    • 0014402757 scopus 로고
    • Action of pancreatic lipase on aggregated glyceride molecules in an isotropic system
    • 29. Entressangles, B. and Desnuelle, P. Action of pancreatic lipase on aggregated glyceride molecules in an isotropic system. Biochim. Biophys. Acta 1968, 159, 285-295
    • (1968) Biochim. Biophys. Acta , vol.159 , pp. 285-295
    • Entressangles, B.1    Desnuelle, P.2
  • 30
    • 0027506517 scopus 로고
    • Stereoselective hydrolysis of triglycerides by animal and microbial lipases
    • 30. Rogalska, E., Cudrey, C., Ferrato, F., and Verger, R. Stereoselective hydrolysis of triglycerides by animal and microbial lipases. Chirality 1993, 5, 24-30
    • (1993) Chirality , vol.5 , pp. 24-30
    • Rogalska, E.1    Cudrey, C.2    Ferrato, F.3    Verger, R.4
  • 31
    • 0027475881 scopus 로고
    • Controlling lipase stereoselectivity via the surface pressure
    • 31. Rogalska, E., Ransac, S., and Verger, R. Controlling lipase stereoselectivity via the surface pressure. J. Biol. Chem. 1993, 268, 792-794
    • (1993) J. Biol. Chem. , vol.268 , pp. 792-794
    • Rogalska, E.1    Ransac, S.2    Verger, R.3


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