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Volumn 48, Issue 2, 2000, Pages 524-530

Enantiomeric synthesis of (S)-2-methylbutanoic acid methyl ester, apple flavor, using lipases in organic solvent

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLBUTYRIC ACID; 2-METHYLBUTYRATE; BUTYRIC ACID DERIVATIVE; ESTER; FLAVORING AGENT; ORGANIC SOLVENT; SOLVENT; TRIACYLGLYCEROL LIPASE;

EID: 0000224981     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990871w     Document Type: Article
Times cited : (27)

References (43)
  • 1
    • 0343261144 scopus 로고
    • Acid catalysis in liquid ammonia. III. Effect of α-substituents on the ammonolysis of esters
    • Audrieth, L. F.; Kleinberg, J. Acid catalysis in liquid ammonia. III. Effect of α-substituents on the ammonolysis of esters. J. Org. Chem. 1938, 3, 312-316.
    • (1938) J. Org. Chem. , vol.3 , pp. 312-316
    • Audrieth, L.F.1    Kleinberg, J.2
  • 2
    • 0000109370 scopus 로고
    • Studies of the heterogeneity of a Candida cylindracea (rugosa) lipase: Monitoring of esterolytic activity and enantioselectivity by chiral liquid chromatography
    • Allenmark, S.; Ohlsson, A. Studies of the heterogeneity of a Candida cylindracea (rugosa) lipase: Monitoring of esterolytic activity and enantioselectivity by chiral liquid chromatography. Biocatalysis 1992, 6, 211-221.
    • (1992) Biocatalysis , vol.6 , pp. 211-221
    • Allenmark, S.1    Ohlsson, A.2
  • 4
    • 0013855462 scopus 로고
    • Etude cinetique de l'action de la lipase pancretique sur des triglycerides en emulsion. Essai d'une enzymologie en milieu heterogene
    • Benzonana, G.; Desnuelle, P. Etude cinetique de l'action de la lipase pancretique sur des triglycerides en emulsion. Essai d'une enzymologie en milieu heterogene. Biochim. Biophys. Acta 1965, 105, 121-136.
    • (1965) Biochim. Biophys. Acta , vol.105 , pp. 121-136
    • Benzonana, G.1    Desnuelle, P.2
  • 5
    • 0027483513 scopus 로고
    • Water activity dose not influence the enantioselectivity of lipase PS and lipoprotein lipase in organic solvents
    • Bovara, R.; Carrea, G.; Ottilina, G.; Riva, S. Water activity dose not influence the enantioselectivity of lipase PS and lipoprotein lipase in organic solvents. Biotechnol. Lett. 1993, 15, 169-174.
    • (1993) Biotechnol. Lett. , vol.15 , pp. 169-174
    • Bovara, R.1    Carrea, G.2    Ottilina, G.3    Riva, S.4
  • 6
    • 0015606921 scopus 로고
    • A model of pancreatic lipase and the orientation of enzymes at interfaces
    • Brockerhoff, H. A model of pancreatic lipase and the orientation of enzymes at interfaces. Chem. Phys. Lipids 1973, 10, 215-222.
    • (1973) Chem. Phys. Lipids , vol.10 , pp. 215-222
    • Brockerhoff, H.1
  • 7
    • 20644469267 scopus 로고
    • Quantitative analysis of biochemical kinetic resolutions of enantiomers
    • Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; 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
  • 8
    • 0027909093 scopus 로고
    • Dramatic enhancement of enzymatic activity in organic solvents by lyoprotectants
    • Dabulis, K.; Klibanov, A. M. Dramatic enhancement of enzymatic activity in organic solvents by lyoprotectants. Biotechnol. Bioeng. 1993, 41, 566-571.
    • (1993) Biotechnol. Bioeng. , vol.41 , pp. 566-571
    • Dabulis, K.1    Klibanov, A.M.2
  • 9
    • 0027388770 scopus 로고
    • News from the interface: The molecular structures of triglyceride lipases
    • Derewenda, Z. S.; Sharp, A. M. News from the interface: the molecular structures of triglyceride lipases. Trends Biochem. Sci. 1993, 18, 20-25.
    • (1993) Trends Biochem. Sci. , vol.18 , pp. 20-25
    • Derewenda, Z.S.1    Sharp, A.M.2
  • 10
    • 0028809194 scopus 로고
    • Influence of water activity on the synthesis of triolein catalyzed by immobilized Mucor miehei lipase
    • Dudal, Y.; Lortie, R. Influence of water activity on the synthesis of triolein catalyzed by immobilized Mucor miehei lipase. Biotechnol. Bioeng. 1995, 45, 129-134.
    • (1995) Biotechnol. Bioeng. , vol.45 , pp. 129-134
    • Dudal, Y.1    Lortie, R.2
  • 11
    • 51249165212 scopus 로고
    • Lipase-catalyzed enantioselective acidolysis of chiral 2-methylalkanoates
    • Engel, K. H. Lipase-catalyzed enantioselective acidolysis of chiral 2-methylalkanoates. J. Am. Oil Chem. Soc. 1992, 69, 146-150.
    • (1992) J. Am. Oil Chem. Soc. , vol.69 , pp. 146-150
    • Engel, K.H.1
  • 12
    • 0000626186 scopus 로고
    • How can the solvent affect enzyme enantioselectivity?
    • Fitzpatrick, P. A.; Klibanov, A. M. How can the solvent affect enzyme enantioselectivity? J. Am. Chem. Soc. 1991, 113, 3166-3171.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 3166-3171
    • Fitzpatrick, P.A.1    Klibanov, A.M.2
  • 13
    • 0025727798 scopus 로고
    • Temperature as an enantioselective parameter in enzyme resolutions of racemic mixtures
    • Holmberg, E.; Huit, K. Temperature as an enantioselective parameter in enzyme resolutions of racemic mixtures. Biotechnol. Lett. 1991, 13, 323-326.
    • (1991) Biotechnol. Lett. , vol.13 , pp. 323-326
    • Holmberg, E.1    Hult, K.2
  • 14
    • 0025737085 scopus 로고
    • Reaction conditions for the resolution of 2-methylalkanoic acids in esterification and hydrolysis with lipase from Candida cylindracea
    • Holmberg, E.; Holmquist, M.; Hendenstroem, E.; Berglund, P.; Norin, T.; Hoeberg, H. E.; Hult, K. Reaction conditions for the resolution of 2-methylalkanoic acids in esterification and hydrolysis with lipase from Candida cylindracea. Appl. Microbiol. Biotechnol. 1991, 35, 572-578.
    • (1991) Appl. Microbiol. Biotechnol. , vol.35 , pp. 572-578
    • Holmberg, E.1    Holmquist, M.2    Hendenstroem, E.3    Berglund, P.4    Norin, T.5    Hoeberg, H.E.6    Hult, K.7
  • 15
    • 0342391578 scopus 로고    scopus 로고
    • Preparation of surfactant-coated lipases utilizing the molecular imprinting technique
    • Kamiya, N.; Goto, M. Preparation of surfactant-coated lipases utilizing the molecular imprinting technique. J. Biotechnol. 1998, 52, 81-88.
    • (1998) J. Biotechnol. , vol.52 , pp. 81-88
    • Kamiya, N.1    Goto, M.2
  • 16
    • 0024454134 scopus 로고
    • Esterification of chiral secondary alcohols with fatty acid in organic solvents by poly(ethylene glycol)-modified lipase
    • Kikkawa, S.; Takahashi, K.; Katada, T.; Inada, Y. Esterification of chiral secondary alcohols with fatty acid in organic solvents by poly(ethylene glycol)-modified lipase. Biochem. Int. 1989, 19, 1125-1131.
    • (1989) Biochem. Int. , vol.19 , pp. 1125-1131
    • Kikkawa, S.1    Takahashi, K.2    Katada, T.3    Inada, Y.4
  • 17
    • 0021699443 scopus 로고
    • Effects of organic solvents on lipase for fat splitting
    • Kim, K. H.; Kwon, D. Y.; Rhee, J. S. Effects of organic solvents on lipase for fat splitting. Lipids 1984, 19, 975-977.
    • (1984) Lipids , vol.19 , pp. 975-977
    • Kim, K.H.1    Kwon, D.Y.2    Rhee, J.S.3
  • 18
    • 0022724718 scopus 로고
    • Enzyme work in organic solvents
    • Klibanov, A. M. Enzyme work in organic solvents. Chemtech 1986, 16, 354-359.
    • (1986) Chemtech , vol.16 , pp. 354-359
    • Klibanov, A.M.1
  • 19
    • 0028928260 scopus 로고
    • Enzyme memory - What is remembered and why?
    • Klibanov, A. M. Enzyme memory - What is remembered and why? Nature 1995, 374, 596.
    • (1995) Nature , vol.374 , pp. 596
    • Klibanov, A.M.1
  • 20
    • 0014235891 scopus 로고
    • The catalytic and regulatory properties of enzymes
    • Koshland, D. E.; Neet, K. E. The catalytic and regulatory properties of enzymes. Annu. Rev. Biochem. 1968, 37, 359-410.
    • (1968) Annu. Rev. Biochem. , vol.37 , pp. 359-410
    • Koshland, D.E.1    Neet, K.E.2
  • 21
    • 0008711036 scopus 로고
    • Synthesis of stereoisomer trifluoroethylmandelates and their stereospecificities for the uses as the substrate of lipase in organic solvent
    • Kwon, D. Y. Synthesis of stereoisomer trifluoroethylmandelates and their stereospecificities for the uses as the substrate of lipase in organic solvent. J. Kor. Chem. Soc. 1992, 36, 125-130.
    • (1992) J. Kor. Chem. Soc. , vol.36 , pp. 125-130
    • Kwon, D.Y.1
  • 22
    • 51249183030 scopus 로고
    • Immobilization of lipase for fat splitting
    • Kwon, D. Y.; Rhee, J. S. Immobilization of lipase for fat splitting. Kor. J. Chem. Eng. 1983, 1, 153-156.
    • (1983) Kor. J. Chem. Eng. , vol.1 , pp. 153-156
    • Kwon, D.Y.1    Rhee, J.S.2
  • 24
    • 0030283991 scopus 로고    scopus 로고
    • Synthesis of medium-chain glycerides by lipase in organic solvent
    • Kwon, D. Y.; Song, H. N.; Yoon, S. H. Synthesis of medium-chain glycerides by lipase in organic solvent. J. Am. Oil Chem. Soc. 1996, 73, 1521-1525.
    • (1996) J. Am. Oil Chem. Soc. , vol.73 , pp. 1521-1525
    • Kwon, D.Y.1    Song, H.N.2    Yoon, S.H.3
  • 25
    • 0031258189 scopus 로고    scopus 로고
    • Esterification patterns of lipases for synthesizing tricaproylglycerols in organic solvent
    • Kwon, D. Y.; Song, H. N.; Yoon, S. H. Esterification patterns of lipases for synthesizing tricaproylglycerols in organic solvent. J. Am. Oil Chem. Soc. 1997, 74, 1287-1290.
    • (1997) J. Am. Oil Chem. Soc. , vol.74 , pp. 1287-1290
    • Kwon, D.Y.1    Song, H.N.2    Yoon, S.H.3
  • 26
    • 0342826303 scopus 로고    scopus 로고
    • Separation of enantiomers of (S)- and (R)-2-methylbutanoic acid methyl ester using chiral GC column
    • Kwon, D. Y.; Yang, H. J.; Yoon, S. H. Separation of enantiomers of (S)- and (R)-2-methylbutanoic acid methyl ester using chiral GC column. Food Sci. Biotechnol. 1999, 8, 139-141.
    • (1999) Food Sci. Biotechnol. , vol.8 , pp. 139-141
    • Kwon, D.Y.1    Yang, H.J.2    Yoon, S.H.3
  • 27
    • 33751330608 scopus 로고
    • The determination of enzyme dissociation constants
    • Lineweaver, H.; Burk, D. The determination of enzyme dissociation constants. J. Am. Chem. Soc. 1934, 56, 658-666.
    • (1934) J. Am. Chem. Soc. , vol.56 , pp. 658-666
    • Lineweaver, H.1    Burk, D.2
  • 29
    • 0008712344 scopus 로고
    • Microbial lipases catalysts for the interesterification of oils and fats
    • Ratledge, C., Dawson, P., Rattray, J., Eds.; AOCS Press: Champaign, IL
    • Macrae, A. R. Microbial lipases catalysts for the interesterification of oils and fats. In Biotechnology for the Oils and Fats Industry; Ratledge, C., Dawson, P., Rattray, J., Eds.; AOCS Press: Champaign, IL, 1984; pp 189-198.
    • (1984) Biotechnology for the Oils and Fats Industry , pp. 189-198
    • Macrae, A.R.1
  • 31
    • 0007886775 scopus 로고
    • Volatile flavor compounds of wood apple and a processed product
    • Macleod, A. J.; Pieris, N. M. Volatile flavor compounds of wood apple and a processed product. J. Agric. Food Chem. 1981, 29, 49-53.
    • (1981) J. Agric. Food Chem. , vol.29 , pp. 49-53
    • Macleod, A.J.1    Pieris, N.M.2
  • 32
    • 0000442242 scopus 로고
    • Kinetics of triglyceride lipases
    • Woolley, P., Petersen, S. B., Eds.; Cambridge University Press: Cambridge, U.K.
    • Martinelle, M.; Huit, K. Kinetics of triglyceride lipases. In Lipase; Woolley, P., Petersen, S. B., Eds.; Cambridge University Press: Cambridge, U.K., 1994; pp 159-180.
    • (1994) Lipase , pp. 159-180
    • Martinelle, M.1    Huit, K.2
  • 33
    • 0030570503 scopus 로고    scopus 로고
    • The influence of the mode of enzyme preparation on enzymatic enantioselectivity in organic solvents and its temperature dependence
    • Noritomi, H.; Almarsson, O.; Barletta, G. L.; Klibanov, A. M. The influence of the mode of enzyme preparation on enzymatic enantioselectivity in organic solvents and its temperature dependence. Biotechnol. Bioeng. 1996, 51, 95-99.
    • (1996) Biotechnol. Bioeng. , vol.51 , pp. 95-99
    • Noritomi, H.1    Almarsson, O.2    Barletta, G.L.3    Klibanov, A.M.4
  • 34
    • 0026451061 scopus 로고
    • Effect of the enzyme form on the activity, stability and enantioselectivity of lipoprotein lipase in toluene
    • Ottolina, G.; Carrea, G.; Riva, S.; Sartore, L.; Veronese, F. M. Effect of the enzyme form on the activity, stability and enantioselectivity of lipoprotein lipase in toluene. Biotechnol. Lett. 1992, 14, 947-952.
    • (1992) Biotechnol. Lett. , vol.14 , pp. 947-952
    • Ottolina, G.1    Carrea, G.2    Riva, S.3    Sartore, L.4    Veronese, F.M.5
  • 35
    • 0026863988 scopus 로고
    • Temperature effects on stereochemistry of enzymatic reactions
    • Phillips, R. S. Temperature effects on stereochemistry of enzymatic reactions. Enzymol Microbiol. Technol 1992, 14, 417-419.
    • (1992) Enzymol Microbiol. Technol , vol.14 , pp. 417-419
    • Phillips, R.S.1
  • 36
    • 0024297108 scopus 로고
    • Inhibitor-induced enzyme activation in organic solvents
    • Russel, A.; Klibanov, A. M. Inhibitor-induced enzyme activation in organic solvents. J. Biol. Chem. 1988, 263, 11624-11625.
    • (1988) J. Biol. Chem. , vol.263 , pp. 11624-11625
    • Russel, A.1    Klibanov, A.M.2
  • 37
    • 0001406913 scopus 로고
    • Action de la lipase pancreatique sur les esters en emulsion
    • Sarda, L.; Desnuelle, P. Action de la lipase pancreatique sur les esters en emulsion. Biochim. Biophys. Acta 1958, 30, 513-520.
    • (1958) Biochim. Biophys. Acta , vol.30 , pp. 513-520
    • Sarda, L.1    Desnuelle, P.2
  • 38
    • 0030737031 scopus 로고    scopus 로고
    • Molecular imprinting: Assembling the molecular cast
    • Vulfson, E. N.; Alexander, C.; Whitcombe, M. J. Molecular imprinting: Assembling the molecular cast. Chem. Brit. 1997, 33, 23-26.
    • (1997) Chem. Brit. , vol.33 , pp. 23-26
    • Vulfson, E.N.1    Alexander, C.2    Whitcombe, M.J.3
  • 39
    • 0242528545 scopus 로고
    • Enantiopreference of lipase from Pseudomonas cepacia toward primary alcohols
    • Weissfloch, A. N. E.; Kazlauskas, R. J. Enantiopreference of lipase from Pseudomonas cepacia toward primary alcohols. J. Org. Chem. 1995, 60, 6959-6969.
    • (1995) J. Org. Chem. , vol.60 , pp. 6959-6969
    • Weissfloch, A.N.E.1    Kazlauskas, R.J.2
  • 40
    • 0343703438 scopus 로고    scopus 로고
    • Lipase-catalyzed stereoselective esterification of di-menthol in organic solvent using acid anhydrides as acylation agents
    • Wen, H. W.; Akoh, C. C.; Phillips, R. S. Lipase-catalyzed stereoselective esterification of di-menthol in organic solvent using acid anhydrides as acylation agents. Enzymol. Microbiol. Technol. 1996, 18, 536-539.
    • (1996) Enzymol. Microbiol. Technol. , vol.18 , pp. 536-539
    • Wen, H.W.1    Akoh, C.C.2    Phillips, R.S.3
  • 41
    • 0028302684 scopus 로고
    • The solvent dependence of enzyme specificity
    • Wescott, C. R.; Klibanov, A. M. The solvent dependence of enzyme specificity. Biochim. Biophys. Acta 1994, 1206, 1-9.
    • (1994) Biochim. Biophys. Acta , vol.1206 , pp. 1-9
    • Wescott, C.R.1    Klibanov, A.M.2
  • 42
    • 0021763770 scopus 로고
    • Enzymatic catalysis in organic media at 100°C
    • Zaks, A.; Klibanov, A. M. Enzymatic catalysis in organic media at 100°C. Science 1984, 224, 1249-1251.
    • (1984) Science , vol.224 , pp. 1249-1251
    • Zaks, A.1    Klibanov, A.M.2
  • 43
    • 0024278258 scopus 로고
    • Enzymatic catalysis in nonaqueous solvents
    • Zaks, A.; Klibanov, A. M. Enzymatic catalysis in nonaqueous solvents. J. Biol. Chem. 1988, 263, 3194-3201.
    • (1988) J. Biol. Chem. , vol.263 , pp. 3194-3201
    • Zaks, A.1    Klibanov, A.M.2


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