메뉴 건너뛰기




Volumn 58, Issue 10, 2010, Pages 6328-6333

Preparation of passion fruit-typical 2-alkyl ester enantiomers via lipase-catalyzed kinetic resolution

Author keywords

2 alkyl esters; Candida antarctica lipase B; Candida cylindracea lipase; Kinetic resolution; Secondary alcohols

Indexed keywords

ALCOHOL DERIVATIVE; ESTER; IMMOBILIZED ENZYME; LIPASE B, CANDIDA ANTARCTICA; TRIACYLGLYCEROL LIPASE; VOLATILE FATTY ACID; FUNGAL PROTEIN;

EID: 77952599133     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf100432s     Document Type: Article
Times cited : (8)

References (28)
  • 1
    • 36749034610 scopus 로고
    • Biogenesis of chiral aroma compounds and their analytical characterization at trace level
    • Adda, J., Ed.; Elsevier: Amsterdam, Netherlands
    • Tressl, R. and Engel, K.-H. Biogenesis of chiral aroma compounds and their analytical characterization at trace level. In Progress in Flavour Research; Adda, J., Ed.; Elsevier: Amsterdam, Netherlands, 1985; pp 441 - 455.
    • (1985) Progress in Flavour Research , pp. 441-455
    • Tressl, R.1    Engel, K.-H.2
  • 2
    • 38049093659 scopus 로고
    • Differentiation of yellow and purple passion fruits by investigation of their ester composition
    • Engel, K.-H.; Tressl, R. Differentiation of yellow and purple passion fruits by investigation of their ester composition Chem. Mikrobiol. Technol. Lebensm. 1983, 8, 33-39
    • (1983) Chem. Mikrobiol. Technol. Lebensm. , vol.8 , pp. 33-39
    • Engel, K.-H.1    Tressl, R.2
  • 3
    • 38049049253 scopus 로고    scopus 로고
    • Enantioselelective analysis of secondary alcohols and their esters in purple and yellow passion fruits
    • Strohalm, H.; Dregus, M.; Wahl, A.; Engel, K.-H. Enantioselelective analysis of secondary alcohols and their esters in purple and yellow passion fruits J. Agric. Food Chem. 2007, 55, 10339-10344
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 10339-10344
    • Strohalm, H.1    Dregus, M.2    Wahl, A.3    Engel, K.-H.4
  • 4
    • 10844227997 scopus 로고    scopus 로고
    • Application of lipases in kinetic resolution of racemates
    • Ghanem, A.; Aboul-Enein, H. Y. Application of lipases in kinetic resolution of racemates Chirality 2005, 17, 1-15
    • (2005) Chirality , vol.17 , pp. 1-15
    • Ghanem, A.1    Aboul-Enein, H.Y.2
  • 6
    • 84978734472 scopus 로고    scopus 로고
    • Biotransformations with lipases
    • 2 nd ed; Kelly, D. R., Ed.; Wiley-VCH Verlag: Weinheim, Germany
    • Kazlauskas, R. J.; Bornscheuer, U. T. Biotransformations with lipases. In Biotechnology, 2 nd ed; Kelly, D. R., Ed.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Vol. 8a, pp 37 - 191.
    • (1998) Biotechnology , vol.8 , pp. 37-191
    • Kazlauskas, R.J.1    Bornscheuer, U.T.2    Kelly, D.R.3
  • 7
    • 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 rugosa
    • Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; 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 rugosa J. Org. Chem. 1991, 56, 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
  • 8
    • 36749098818 scopus 로고
    • Investigation of chiral compounds in biological systems by chromatographic micromethods
    • Schreier, P., Ed.; de Gruyter Verlag: Berlin, Germany
    • Engel, K.-H. Investigation of chiral compounds in biological systems by chromatographic micromethods. In Bioflavour '87. Schreier, P., Ed.; de Gruyter Verlag: Berlin, Germany, 1988; pp 75 - 88.
    • (1988) Bioflavour '87 , pp. 75-88
    • Engel, K.-H.1
  • 9
    • 34249976152 scopus 로고
    • Kinetic resolution of heptan-2-ol-enantiomers by lipase-catalyzed esterification in organic solvent
    • Engel, K.-H.; Bohnen, M.; Tressl, R. Kinetic resolution of heptan-2-ol-enantiomers by lipase-catalyzed esterification in organic solvent Z. Lebensm. Unters. Forsch. 1989, 188, 144-147
    • (1989) Z. Lebensm. Unters. Forsch. , vol.188 , pp. 144-147
    • Engel, K.-H.1    Bohnen, M.2    Tressl, R.3
  • 10
    • 0003046977 scopus 로고
    • Enantioselective lipase catalyzed esterification in organic medium for preparation of optically active secondary alcohols
    • Gerlach, D.; Lutz, D.; Mey, B.; Schreier, P. Enantioselective lipase catalyzed esterification in organic medium for preparation of optically active secondary alcohols Z. Lebensm. Unters. Forsch. 1989, 189, 141-143
    • (1989) Z. Lebensm. Unters. Forsch. , vol.189 , pp. 141-143
    • Gerlach, D.1    Lutz, D.2    Mey, B.3    Schreier, P.4
  • 11
    • 0041561165 scopus 로고
    • Esterification in organic media for preparation of optically active secondary alcohols: Effects of reaction conditions
    • Gerlach, D.; Schreier, P. Esterification in organic media for preparation of optically active secondary alcohols: effects of reaction conditions Biocatal. Biotransform. 1989, 2, 257-263
    • (1989) Biocatal. Biotransform. , vol.2 , pp. 257-263
    • Gerlach, D.1    Schreier, P.2
  • 12
    • 0031795317 scopus 로고    scopus 로고
    • One biocatalyst-many applications: The use of Candida antarctica B-lipase in organic synthesis
    • Anderson, E. M.; Larsson, K. M.; Kirk, O. One biocatalyst-many applications: The use of Candida antarctica B-lipase in organic synthesis Biocatal. Biotransform. 1998, 16, 181-204
    • (1998) Biocatal. Biotransform. , vol.16 , pp. 181-204
    • Anderson, E.M.1    Larsson, K.M.2    Kirk, O.3
  • 13
    • 0034300323 scopus 로고    scopus 로고
    • Enzymatic resolution of racemic secondary alcohols by Lipase B from Candida antartica
    • Patel, R. N.; Banerjee, A.; Nanduri, V.; Goswami, A.; Comezoglu, F. T. Enzymatic resolution of racemic secondary alcohols by Lipase B from Candida antartica J. Am. Oil Chem. Soc. 2000, 77, 1015-1019
    • (2000) J. Am. Oil Chem. Soc. , vol.77 , pp. 1015-1019
    • Patel, R.N.1    Banerjee, A.2    Nanduri, V.3    Goswami, A.4    Comezoglu, F.T.5
  • 14
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. Quantitative analyses 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
  • 15
    • 0027897680 scopus 로고
    • A simple method to determine the enantiomeric ration enantioselective biocatalysis
    • Rakels, J. L. L.; Straathof, A. J. J.; Heijnen, J. J. A simple method to determine the enantiomeric ration enantioselective biocatalysis Enzyme Microb. Technol. 1993, 15, 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
  • 17
    • 78650601431 scopus 로고
    • 1 st ed; Springer Verlag: Berlin, Heidelberg, Germany
    • Barman, T. E. Enzyme handbook Vol. II, 1 st ed; Springer Verlag: Berlin, Heidelberg, Germany, 1969.
    • (1969) Enzyme Handbook Vol. II
    • Barman, T.E.1
  • 18
    • 0000298405 scopus 로고    scopus 로고
    • Molecular recognition of sec -alcohol enantiomers by Candida antarctica lipase B
    • Rotticci, D.; Haeffner, F.; Orrenius, C.; Norin, T.; Hult, K. Molecular recognition of sec -alcohol enantiomers by Candida antarctica lipase B J. Mol. Catal. B: Enzym. 1998, 5, 267-272
    • (1998) J. Mol. Catal. B: Enzym. , vol.5 , pp. 267-272
    • Rotticci, D.1    Haeffner, F.2    Orrenius, C.3    Norin, T.4    Hult, K.5
  • 19
    • 0021671748 scopus 로고
    • Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification
    • Cambou, B.; Klibanov, A. M. Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: asymmetric hydrolysis, esterification, and transesterification Biotechnol. Bioeng. 1984, 26, 1449-1454
    • (1984) Biotechnol. Bioeng. , vol.26 , pp. 1449-1454
    • Cambou, B.1    Klibanov, A.M.2
  • 20
    • 0010570664 scopus 로고
    • Kinetic resolution of secondary alcohols with commercial lipases: Application to rootworm sex pheromone synthesis
    • Sonnet, P. E.; Baillargeon, M. E. Kinetic resolution of secondary alcohols with commercial lipases: application to rootworm sex pheromone synthesis J. Chem. Ecol. 1987, 13, 1279-1292
    • (1987) J. Chem. Ecol. , vol.13 , pp. 1279-1292
    • Sonnet, P.E.1    Baillargeon, M.E.2
  • 21
    • 0043207487 scopus 로고
    • Screening of lipases for the enantiomer resolution of R,S-2-octanol by esterification in organic medium
    • Gerlach, D.; Missel, C.; Schreier, P. Screening of lipases for the enantiomer resolution of R,S-2-octanol by esterification in organic medium Z. Lebensm. Unters. Forsch. 1988, 186, 315-318
    • (1988) Z. Lebensm. Unters. Forsch. , vol.186 , pp. 315-318
    • Gerlach, D.1    Missel, C.2    Schreier, P.3
  • 22
    • 0026528597 scopus 로고
    • Solvent-induced inversion of enantioselectivity in lipase-catalyzed esterification of phenoxypropionic acids
    • Ueji, S.; Fujino, R.; Okubo, N.; Miyazawa, T.; Kurita, S.; Kitadani, M.; Muromatsu, A. Solvent-induced inversion of enantioselectivity in lipase-catalyzed esterification of phenoxypropionic acids Biotechnol. Lett. 1992, 14, 163-168
    • (1992) Biotechnol. Lett. , vol.14 , pp. 163-168
    • Ueji, S.1    Fujino, R.2    Okubo, N.3    Miyazawa, T.4    Kurita, S.5    Kitadani, M.6    Muromatsu, A.7
  • 23
    • 16244405562 scopus 로고    scopus 로고
    • Immobilized enzymes: Science or art?
    • Cao, L. Immobilized enzymes: science or art? Biocatal. Biotransform. 2005, 9, 217-226
    • (2005) Biocatal. Biotransform. , vol.9 , pp. 217-226
    • Cao, L.1
  • 24
    • 0037025268 scopus 로고    scopus 로고
    • Modulation of the enantioselectivity of Candida antarctica B lipase via conformational engineering: Kinetic resolution of (±)-α-hydroxy- phenylacetic acid derivatives
    • Palomo, J. M.; Fernández-Lorente, G.; Mateo, C.; Fuentes, M.; Fernández-Lafuente, R.; Guisan, J. M. Modulation of the enantioselectivity of Candida antarctica B lipase via conformational engineering: kinetic resolution of (±)-α-hydroxy-phenylacetic acid derivatives Tetrahedron: Asymmetry 2002, 13, 1337-1345
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1337-1345
    • Palomo, J.M.1    Fernández-Lorente, G.2    Mateo, C.3    Fuentes, M.4    Fernández-Lafuente, R.5    Guisan, J.M.6
  • 27
    • 56649112860 scopus 로고    scopus 로고
    • Wheat germ lipase catalyzed kinetic resolution of secondary alcohols in non-aqueous media
    • Xia, X.; Wang, Y.-H.; Yang, B.; Wang, X. Wheat germ lipase catalyzed kinetic resolution of secondary alcohols in non-aqueous media Biotechnol. Lett. 2009, 31, 83-87
    • (2009) Biotechnol. Lett. , vol.31 , pp. 83-87
    • Xia, X.1    Wang, Y.-H.2    Yang, B.3    Wang, X.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.