Improved production of ethyl-(R)-2-hydroxy-4-phenylbutyrate with pretreated Saccharomyces cerevisiae in water/organic solvent two-liquid phase systems

Biocatalysis and Biotransformation

Volumn 27, Issue 3, 2009, Pages 211-218

  Shi, Yu Gang ^a   Fang, Yun ^a   Wu, Hong Ping ^a   Li, Feng ^a   Zuo, Xue Qin ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Asymmetric reduction; Baker's yeast; Ethyl (R) 2 hydroxy 4 phenylbutyrate; Two liquid phase system

Indexed keywords

ASYMMETRIC REDUCTION; BAKER'S YEAST; CATALYTIC ACTIVITY; CO-SUBSTRATE; CONCENTRATION OF; ETHYL-(R)-2-HYDROXY-4-PHENYLBUTYRATE; HIGH ACTIVITY; MOLAR CONVERSION; PHOSPHATE BUFFERS; PRODUCT INHIBITION; SACCHAROMYCES CEREVISIAE; TWO-LIQUID PHASE SYSTEM;

BENZENE; CHLORINE COMPOUNDS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ENZYME INHIBITION; ETHANOL; LIQUIDS; SUBSTRATES;

YEAST;

ALCOHOL; ARYLBUTYRIC ACID DERIVATIVE; ETHYL 2 HYDROXY 4 PHENYLBUTYRATE; ETHYL 2 OXO 4 PHENYLBUTYRATE; ORGANIC SOLVENT; PHENACYL CHLORIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; NONHUMAN; REDUCTION; SACCHAROMYCES CEREVISIAE;

SACCHAROMYCES CEREVISIAE;

EID: 68049106059     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420902808333     Document Type: Article

References (22)

1. Chadha A, Manohar M, Soundararajan T, Lokeswari TS. 1996. Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures. Tetrahedron Asymm 7:1571-1572.
2. Dahl AC, Fjedberg M, Madsen JØ.. 1999. Baker's yeast: Improving the d-stereoselectivity in reduction of 3-oxo esters. Tetrahedron Asymm 10:551-559.
3. Dao DH, Kawai Y, Hida K, Hornes S, Nakamura K, Ohno A, Okamura M, Akasaka T. 1998. Stereochemical control in microbial reduction. 30. Reduction of alkyl 2-oxo-4- phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors. Bull Chem Soc Jpn 71:425-432.
4. Fadnavis NW, Radhika KR. 2004. Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: Preparation of (R)-HPB ester. Tetrahedron Asymm 15:3443-3447.
5. Hegeman GD. 1996. Synthesis of enzymes of the mandelate pathway by Pseudomonas putida. J Bacteriol 91:1140-1154.
6. Kaluzna I, Andrew AA, Bonilla M, Martzen MR, Stewart JD. 2002. Enantioselective reductions of ethyl 2-oxo-4- phenylbutyrate by Saccharomyces cerevisiae dehydrogenases. J Mol Catal B Enzym 17:101-105.
7. Lacerda PSB, Ribeiro JB, Leite SGF, Coelho RB, Lima ELS, Antunes OAC. 2006a. Microbial enantioselective reduction of ethyl-2-oxo-4-phenyl-butanoate. Biochem Eng J 28:299-302.
8. Lacerda PSB, Ribeiro JB, Leite SGF, Ferrara MA, Coelho RB, Bon EPS, Lima ELS, Antunes OAC. 2006b. Microbial reduction of ethyl 2-oxo-4-phenylbutyrate. Searching for R-enantioselectivity. New access to the enalapril like ACE inhibitors. Tetrahedron Asymm 17:1186-1188.
9. Li YN, Shi XA, Zong MH, Meng C, Dong YQ, Guo YH. 2007. Asymmetric reduction of 2-octanone in water/organic solvent biphasic system with Baker's yeast FD-12. Enzyme Microb Technol 40:1305-1311.
10. Lou WY, Zong MH, Fan XD, Lu JQ, Du W. 2002. Asymmetric microbial reduction of organosilyl ketone with immobilized Saccharomyces cerevisiae cells in water/organic solvent biphasic system. Prog Biochem Biophys 29:297-301.
11. Nakamura K, Kondo S, Kawai Y, Ohno A. 1993. Stereochemical control in microbial reduction. XXI. Effect of organic solvent on reduction of α-keto esters mediated by bakers' yeast. Bull Chem Soc Jpn 66:2738-2743.
12. Nakamura K, Kinoshita M, Ohno A. 1995a. Structure of solvent affects enantioselectivity of lipase-catalyzed transesterification. Tetrahedron 51:8799-8808.
13. Nakamura K, Kondo S, Nakajima N, Ohno A. 1995b. Mechanistic study for stereochemical control of microbial reduction of α-keto esters in an organic solvent. Tetrahedron 51:687-694.
14. Oda S, Kikuchi Y, Nanishi Y. 1992. Synthesis of optically active mandelic acid via microbial oxidation of racemic 1-phenyl-1, 2-ethanediol. Biosci Biotechnol Biochem 56:1216-1220.
15. Oda S, Inada Y, Kobayashi A, Ohta H. 1998. Production of ethyl (R)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo- 4-phenylbutanoate in an interface bioreactor. Biosci Biotechnol Biochem 62:1762-1767.
16. Ramos JL, Duque E, Gallegos MT, Godoy P, Romos ML, Rojas A, Terán W, Segura A. 2002. Mechanisms of solvent tolerance in gram-negative bacteria. Annu Rev Microbiol 56:743-768.
17. Sheldon RA. 1993. Chirotechnology: Industrial synthesis of optically active compounds. New York: Marcel Dekker Inc. p362-367.
18. Shi YG, Fang Y, Jiang N, Xia YM. 2006a. Enantioselective synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate mediated by Saccharomyces cerevisiae in organic solvents. J Food Sci Biotechnol (Chin) 25:66-73.
19. Shi YG, Fang Y, Jiang N, Xia YM. 2006b. Synthesis of chiral ethyl-2-oxo-4-phenylbutyrate catalyzed by Saccharomyces cerevisiae in aqueous phase. Chem Res App (Chin) 18:426-430.
20. Shi YG, Fang Y, Ren YP, Guan HL, Zhang JY. 2008a. Applying α-phenacyl chloride to the enantioselective reduction of ethyl 2-oxo-4-phenylbutyrate with baker's yeast. J Chem Tech Biotechnol online (www.interscience.com) DOI 10.1002/jctb.2099.
21. Shi YG, Fang Y, Ren YP, Wu HP, Guan HL. 2008b. Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae. J Ind Microbiol Biotechnol 35:1419-1424.
22. Turner JJ, Healy JP, Dobson RCJ, Gerrard JA, Hutton CA. 2005. Two new irreversible inhibitors of dihydrodipicolinate synthase. Bioorg Med Chem Lett 15:995-998.