메뉴 건너뛰기




Volumn 44, Issue 11, 2009, Pages 1270-1275

Biocatalytic synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida krusei SW2026: A practical process for high enantiopurity and product titer

Author keywords

Asymmetric reduction; Biosynthesis; Candida krusei; Ethyl (R) 2 hydroxy 4 phenylbutyrate ((R) HPBE); Ethyl 2 oxo 4 phenylbutyrate (OPBE)

Indexed keywords

ANGIOTENSIN-CONVERTING ENZYME; AQUEOUS MEDIUM; ASYMMETRIC REDUCTION; BIOCATALYTIC SYNTHESIS; BIOTRANSFORMATION REACTIONS; BIPHASIC SYSTEMS; CANDIDA KRUSEI; CO-SUBSTRATE; ENANTIOMERIC EXCESS; ENANTIOPURITY; ETHYL (R)-2-HYDROXY-4-PHENYLBUTYRATE ((R)-HPBE); ETHYL 2-OXO-4-PHENYLBUTYRATE (OPBE); FED BATCHES; GREEN CHEMISTRY; LARGE-SCALE PRODUCTION; MICROBIAL REDUCTION; OPTIMAL CONDITIONS; PHTHALATES; PRACTICAL PROCESS; PRODUCT CONCENTRATION; REDUCTION PROCESS;

EID: 70249098768     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2009.07.011     Document Type: Article
Times cited : (44)

References (37)
  • 1
    • 0035898137 scopus 로고    scopus 로고
    • Stereoselective reduction of alkyl 3-oxobutanoate by carbonyl reductase from Candida magnoliae
    • Yasohara Y., Kizaki N., Hasegawa J., Wada M., Kataoka M., and Shimizu S. Stereoselective reduction of alkyl 3-oxobutanoate by carbonyl reductase from Candida magnoliae. Tetrahedron Asymmetry 12 (2001) 1713-1718
    • (2001) Tetrahedron Asymmetry , vol.12 , pp. 1713-1718
    • Yasohara, Y.1    Kizaki, N.2    Hasegawa, J.3    Wada, M.4    Kataoka, M.5    Shimizu, S.6
  • 2
    • 14944383719 scopus 로고    scopus 로고
    • Asymmetric reduction of a variety of ketones with a recombinant carbonyl reductase: identification of the gene encoding a versatile biocatalyst
    • Ema T., Yagasaki H., Okita N., Nishikawa K., Korenaga T., and Sakai T. Asymmetric reduction of a variety of ketones with a recombinant carbonyl reductase: identification of the gene encoding a versatile biocatalyst. Tetrahedron Asymmetry 16 (2005) 1075-1078
    • (2005) Tetrahedron Asymmetry , vol.16 , pp. 1075-1078
    • Ema, T.1    Yagasaki, H.2    Okita, N.3    Nishikawa, K.4    Korenaga, T.5    Sakai, T.6
  • 3
    • 28844495378 scopus 로고    scopus 로고
    • Reaction engineering studies on beta-ketoester reductions with whole cells of recombinant Saccharomyces cerevisiae
    • Engelking H., Pfaller R., Wich G., and Weuster B.D. Reaction engineering studies on beta-ketoester reductions with whole cells of recombinant Saccharomyces cerevisiae. Enzyme Microb Technol 38 (2006) 536-544
    • (2006) Enzyme Microb Technol , vol.38 , pp. 536-544
    • Engelking, H.1    Pfaller, R.2    Wich, G.3    Weuster, B.D.4
  • 4
    • 0000887143 scopus 로고    scopus 로고
    • Enzymatic synthesis of chiral intermediates for drug development
    • Patel R.N. Enzymatic synthesis of chiral intermediates for drug development. Adv Synth Catal 343 (2001) 527-546
    • (2001) Adv Synth Catal , vol.343 , pp. 527-546
    • Patel, R.N.1
  • 5
    • 0021888747 scopus 로고
    • Angiotensin I-converting enzyme inhibitor derived from an enzymatic hydrolysate of casein
    • Maruyama S., Nakagomi K., Tomizuka N., and Suzuki H. Angiotensin I-converting enzyme inhibitor derived from an enzymatic hydrolysate of casein. Agric Biol Chem 49 (1985) 1405-1409
    • (1985) Agric Biol Chem , vol.49 , pp. 1405-1409
    • Maruyama, S.1    Nakagomi, K.2    Tomizuka, N.3    Suzuki, H.4
  • 6
    • 0024591248 scopus 로고
    • A practical and diastereoselective synthesis of angiotensin converting enzyme-inhibitors
    • Iwasaki G., Kimura R., Numao N., and Kondo K. A practical and diastereoselective synthesis of angiotensin converting enzyme-inhibitors. Chem Pharm Bull 37 (1989) 280-283
    • (1989) Chem Pharm Bull , vol.37 , pp. 280-283
    • Iwasaki, G.1    Kimura, R.2    Numao, N.3    Kondo, K.4
  • 7
    • 0032150224 scopus 로고    scopus 로고
    • Production of ethyl (R)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo-4-phenylbutanoate in an interface bioreactor
    • Oda S., Inada Y., Kobayashi A., and Ohta H. Production of ethyl (R)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo-4-phenylbutanoate in an interface bioreactor. Biosci Biotechnol Biochem 62 (1998) 1762-1767
    • (1998) Biosci Biotechnol Biochem , vol.62 , pp. 1762-1767
    • Oda, S.1    Inada, Y.2    Kobayashi, A.3    Ohta, H.4
  • 8
    • 0028939972 scopus 로고
    • Enzymatic resolution of 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenylbutenoic acid
    • Chadha A., and Manohar M. Enzymatic resolution of 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenylbutenoic acid. Tetrahedron Asymmetry 6 (1995) 651-652
    • (1995) Tetrahedron Asymmetry , vol.6 , pp. 651-652
    • Chadha, A.1    Manohar, M.2
  • 9
    • 0041402634 scopus 로고    scopus 로고
    • Dynamic kinetic resolution of alpha-hydroxy acid esters
    • Huerta F.F., Laxmi Y.R.S., and Backvall J.E. Dynamic kinetic resolution of alpha-hydroxy acid esters. Org Lett 2 (2000) 1037-1040
    • (2000) Org Lett , vol.2 , pp. 1037-1040
    • Huerta, F.F.1    Laxmi, Y.R.S.2    Backvall, J.E.3
  • 10
    • 0037007536 scopus 로고    scopus 로고
    • Membrane reactor development for the kinetic resolution of ethyl 2-hydroxy-4-phenylbutyrate
    • Liese A., Kragl U., Kierkels H., and Schulze B. Membrane reactor development for the kinetic resolution of ethyl 2-hydroxy-4-phenylbutyrate. Enzyme Microb Technol 30 (2002) 673-681
    • (2002) Enzyme Microb Technol , vol.30 , pp. 673-681
    • Liese, A.1    Kragl, U.2    Kierkels, H.3    Schulze, B.4
  • 11
    • 1842735639 scopus 로고    scopus 로고
    • Kinetic resolution of (R,S)-ethyl 2-hydroxyl-4-phenylbutyrate via lipase-catalyzed hydrolysis and transesterification in isooctane
    • Huang S.H., Tsai S.W., and Mol J. Kinetic resolution of (R,S)-ethyl 2-hydroxyl-4-phenylbutyrate via lipase-catalyzed hydrolysis and transesterification in isooctane. J Mol Catal B: Enzym 28 (2004) 65-69
    • (2004) J Mol Catal B: Enzym , vol.28 , pp. 65-69
    • Huang, S.H.1    Tsai, S.W.2    Mol, J.3
  • 12
    • 0001462714 scopus 로고
    • Enantioselective hydrogenation of α-ketoacids using platinum catalysts modified with cinchona alkaloids
    • Blaser H.U., and Jalett H.P. Enantioselective hydrogenation of α-ketoacids using platinum catalysts modified with cinchona alkaloids. Stud Surf Sci Catal 78 (1993) 139-146
    • (1993) Stud Surf Sci Catal , vol.78 , pp. 139-146
    • Blaser, H.U.1    Jalett, H.P.2
  • 13
    • 0029969977 scopus 로고    scopus 로고
    • Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures
    • Chadha A., Manohar M., Soundarajan T., and Lokeswari T.S. Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures. Tetrahedron Asymmetry 7 (1996) 1571-1572
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 1571-1572
    • Chadha, A.1    Manohar, M.2    Soundarajan, T.3    Lokeswari, T.S.4
  • 14
    • 0037171619 scopus 로고    scopus 로고
    • Enantioselective reductions of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae dehydrogenases
    • Kaluzna I., Andrew A.A., Bonilla M., Martzen M.R., and Stewart J.D. Enantioselective reductions of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae dehydrogenases. J Mol Catal B: Enzym 17 (2002) 101-105
    • (2002) J Mol Catal B: Enzym , vol.17 , pp. 101-105
    • Kaluzna, I.1    Andrew, A.A.2    Bonilla, M.3    Martzen, M.R.4    Stewart, J.D.5
  • 15
    • 7444232716 scopus 로고    scopus 로고
    • Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: preparation of (R)-HPB ester
    • Fadnavis N.W., and Radhika K.R. Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: preparation of (R)-HPB ester. Tetrehedron Asymmetry 15 (2004) 3443-3447
    • (2004) Tetrehedron Asymmetry , vol.15 , pp. 3443-3447
    • Fadnavis, N.W.1    Radhika, K.R.2
  • 16
    • 23644444887 scopus 로고    scopus 로고
    • Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH)
    • Inoue K., Makino Y., and Itoh N. Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH). Tetrahedron Asymmetry 16 (2005) 2539-2549
    • (2005) Tetrahedron Asymmetry , vol.16 , pp. 2539-2549
    • Inoue, K.1    Makino, Y.2    Itoh, N.3
  • 17
    • 33745069991 scopus 로고    scopus 로고
    • Daucus carota L. mediated bioreduction of prochiral ketones
    • Blanchard N., and Weghe P. Daucus carota L. mediated bioreduction of prochiral ketones. Org Biomol Chem 4 (2006) 2348-2353
    • (2006) Org Biomol Chem , vol.4 , pp. 2348-2353
    • Blanchard, N.1    Weghe, P.2
  • 18
    • 33646922291 scopus 로고    scopus 로고
    • Microbial reduction of ethyl 2-oxo-4-phenylbutyrate. Searching for R-enantioselectivity. New access to the enalapril like ACE inhibitors
    • Lacerda P.S.B., Ribeiro J.B., Leite S.G.F., Ferrara M.A., Coelho R.B., Bon E.P.S., et al. Microbial reduction of ethyl 2-oxo-4-phenylbutyrate. Searching for R-enantioselectivity. New access to the enalapril like ACE inhibitors. Tetrahedron Asymmetry 17 (2006) 1186-1188
    • (2006) Tetrahedron Asymmetry , vol.17 , pp. 1186-1188
    • Lacerda, P.S.B.1    Ribeiro, J.B.2    Leite, S.G.F.3    Ferrara, M.A.4    Coelho, R.B.5    Bon, E.P.S.6
  • 20
    • 50949127503 scopus 로고    scopus 로고
    • Preparation the key intermediate of angiotensin-converting enzyme (ACE) inhibitors: high enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21
    • Chen Y.Z., Lin H., Xu X.Y., Xia S., and Wang L. Preparation the key intermediate of angiotensin-converting enzyme (ACE) inhibitors: high enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21. Adv Synth Catal 350 (2008) 426-430
    • (2008) Adv Synth Catal , vol.350 , pp. 426-430
    • Chen, Y.Z.1    Lin, H.2    Xu, X.Y.3    Xia, S.4    Wang, L.5
  • 21
    • 0000947096 scopus 로고
    • A simple preparation of (R)-2-hydroxy-4-phenylbutanoic acid
    • Sugai T., and Ohta H. A simple preparation of (R)-2-hydroxy-4-phenylbutanoic acid. Agric Biol Chem 55 (1991) 293-294
    • (1991) Agric Biol Chem , vol.55 , pp. 293-294
    • Sugai, T.1    Ohta, H.2
  • 22
    • 0034714254 scopus 로고    scopus 로고
    • New technical synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate of high enantiomeric purity
    • Herold P., Indolese A.F., Jalett H.P., Siegrist U., and Blaser H.U. New technical synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate of high enantiomeric purity. Tetrehedron 56 (2000) 6497-6499
    • (2000) Tetrehedron , vol.56 , pp. 6497-6499
    • Herold, P.1    Indolese, A.F.2    Jalett, H.P.3    Siegrist, U.4    Blaser, H.U.5
  • 23
    • 0035806465 scopus 로고    scopus 로고
    • A practical synthesis of ethyl (R)- and (S)-2-hydroxy-4-phenylbutanoate and d-homophenylalanine ethyl ester hydrochloride from l-malic acid
    • Lin W.Q., He Z., Jing Y., Cui X., Liu H., and Mi A.Q. A practical synthesis of ethyl (R)- and (S)-2-hydroxy-4-phenylbutanoate and d-homophenylalanine ethyl ester hydrochloride from l-malic acid. Tetrehedron Asymmetry 12 (2001) 1583-1587
    • (2001) Tetrehedron Asymmetry , vol.12 , pp. 1583-1587
    • Lin, W.Q.1    He, Z.2    Jing, Y.3    Cui, X.4    Liu, H.5    Mi, A.Q.6
  • 25
    • 0347474982 scopus 로고    scopus 로고
    • Recent developments in asymmetric reduction of ketones with biocatalysts
    • Nakamura K., Yamanaka R., Matsuda T., and Harada T. Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron Asymmetry 14 (2003) 2659-2681
    • (2003) Tetrahedron Asymmetry , vol.14 , pp. 2659-2681
    • Nakamura, K.1    Yamanaka, R.2    Matsuda, T.3    Harada, T.4
  • 26
    • 33845205018 scopus 로고    scopus 로고
    • Asymmetric ketone reduction by a hyperthermophilic alcohol dehydrogenase. The substrate specificity, enantioselectivity and tolerance of organic solvents
    • Zhu D., Malik H.T., and Hua L. Asymmetric ketone reduction by a hyperthermophilic alcohol dehydrogenase. The substrate specificity, enantioselectivity and tolerance of organic solvents. Tetrahedron Asymmetry 17 (2006) 3010-3014
    • (2006) Tetrahedron Asymmetry , vol.17 , pp. 3010-3014
    • Zhu, D.1    Malik, H.T.2    Hua, L.3
  • 27
    • 28944451564 scopus 로고    scopus 로고
    • Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxy-butanoate in an aqueous-organic solvent biphasic system using Aureobasidium pullulans CGMCC 1244
    • He J.Y., Sun Z.H., Ruan W.Q., and Xu Y. Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxy-butanoate in an aqueous-organic solvent biphasic system using Aureobasidium pullulans CGMCC 1244. Process Biochem 41 (2006) 244-249
    • (2006) Process Biochem , vol.41 , pp. 244-249
    • He, J.Y.1    Sun, Z.H.2    Ruan, W.Q.3    Xu, Y.4
  • 28
    • 33847661580 scopus 로고    scopus 로고
    • Asymmetric reduction of 2-octanone in water/organic solvent biphasic system with Baker's yeast FD-12
    • Li Y.N., Shi X.A., Zong M.H., Meng C., Dong Y.Q., and Guo Y.H. Asymmetric reduction of 2-octanone in water/organic solvent biphasic system with Baker's yeast FD-12. Enzyme Microb Technol 40 (2007) 1305-1311
    • (2007) Enzyme Microb Technol , vol.40 , pp. 1305-1311
    • Li, Y.N.1    Shi, X.A.2    Zong, M.H.3    Meng, C.4    Dong, Y.Q.5    Guo, Y.H.6
  • 29
    • 0041152088 scopus 로고    scopus 로고
    • Properties and synthetic applications of enzymes in organic solvents
    • Carrea G., and Riva S. Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Ed 39 (2000) 2226-2254
    • (2000) Angew Chem Int Ed , vol.39 , pp. 2226-2254
    • Carrea, G.1    Riva, S.2
  • 30
    • 0030066698 scopus 로고    scopus 로고
    • Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation
    • Philips R.S. Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol 14 (1996) 13-16
    • (1996) Trends Biotechnol , vol.14 , pp. 13-16
    • Philips, R.S.1
  • 31
    • 14644437141 scopus 로고    scopus 로고
    • Comparison of kinetic resolution between two racemic ibuprofen esters in an enzymic membrane reactor
    • Long W.S., Kow P.C., Kamaruddin A.H., and Bhatia S. Comparison of kinetic resolution between two racemic ibuprofen esters in an enzymic membrane reactor. Process Biochem 40 (2005) 2417-2425
    • (2005) Process Biochem , vol.40 , pp. 2417-2425
    • Long, W.S.1    Kow, P.C.2    Kamaruddin, A.H.3    Bhatia, S.4
  • 32
    • 29544435883 scopus 로고    scopus 로고
    • Cell adaptation to solvent, substrate and product: a successful strategy to overcome product inhibition in a bioconversion system
    • Carvalho C.C.C.R., Poretti A., and Fonseca M.M.R. Cell adaptation to solvent, substrate and product: a successful strategy to overcome product inhibition in a bioconversion system. Appl Microbiol Biotechnol 69 (2005) 268-275
    • (2005) Appl Microbiol Biotechnol , vol.69 , pp. 268-275
    • Carvalho, C.C.C.R.1    Poretti, A.2    Fonseca, M.M.R.3
  • 33
    • 0042967675 scopus 로고    scopus 로고
    • Cofactor recycling mechanism in asymmetric biocatalytic reduction of carbonyl compounds mediated by yeast: which is the efficient electron donor?
    • Zhang B.L., and Pionnier S. Cofactor recycling mechanism in asymmetric biocatalytic reduction of carbonyl compounds mediated by yeast: which is the efficient electron donor?. Chem Eur J 9 (2003) 3604-3610
    • (2003) Chem Eur J , vol.9 , pp. 3604-3610
    • Zhang, B.L.1    Pionnier, S.2
  • 34
    • 0242291798 scopus 로고    scopus 로고
    • Efficient anaerobic whole cell stereoselective bioreduction with recombinant Saccharomyces cerevisiae
    • Katz M., Frejd T., Hägerdal B.H., and Grauslund M.F.G. Efficient anaerobic whole cell stereoselective bioreduction with recombinant Saccharomyces cerevisiae. Biotechnol Bioeng 84 (2003) 573-582
    • (2003) Biotechnol Bioeng , vol.84 , pp. 573-582
    • Katz, M.1    Frejd, T.2    Hägerdal, B.H.3    Grauslund, M.F.G.4
  • 35
    • 0033548083 scopus 로고    scopus 로고
    • Baker's yeast: improving the d-stereoselectivity in reduction of 3-oxo esters
    • Dahl A.C., Fjeldberg M., and Madsen J.O. Baker's yeast: improving the d-stereoselectivity in reduction of 3-oxo esters. Tetrahedron Asymmetry 10 (1999) 551-559
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 551-559
    • Dahl, A.C.1    Fjeldberg, M.2    Madsen, J.O.3
  • 36
    • 0023385987 scopus 로고
    • Rules for optimization of biocatalysis in organic-solvents
    • Laane C., Boeren S., Vos K., and Veeger C. Rules for optimization of biocatalysis in organic-solvents. Biotechnol Bioeng 30 (1987) 81-87
    • (1987) Biotechnol Bioeng , vol.30 , pp. 81-87
    • Laane, C.1    Boeren, S.2    Vos, K.3    Veeger, C.4
  • 37
    • 47049089266 scopus 로고    scopus 로고
    • Asymmetric reduction of substituted α- and β-ketoesters by Bacillus pumilus Phe-C3
    • He C.M., Chang D.L., and Zhang J. Asymmetric reduction of substituted α- and β-ketoesters by Bacillus pumilus Phe-C3. Tetrahedron Asymmetry 19 (2008) 1347-1351
    • (2008) Tetrahedron Asymmetry , vol.19 , pp. 1347-1351
    • He, C.M.1    Chang, D.L.2    Zhang, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.