47
Views
6
CrossRef citations to date
0
Altmetric
Original Article

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

, , , &
Pages 211-218 | Published online: 13 Aug 2009

References

  • Chadha A, Manohar M, Soundararajan T, Lokeswari TS. Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures. Tetrahedron Asymm 1996; 7: 1571–1572
  • Dahl AC, Fjedberg M, Madsen JØ. Baker's yeast: improving the d-stereoselectivity in reduction of 3-oxo esters. Tetrahedron Asymm 1999; 10: 551–559
  • Dao DH, Kawai Y, Hida K, Hornes S, Nakamura K, Ohno A, Okamura M, Akasaka T. 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 1998; 71: 425–432
  • Fadnavis NW, Radhika KR. Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: preparation of (R)-HPB ester. Tetrahedron Asymm 2004; 15: 3443–3447
  • Hegeman GD. Synthesis of enzymes of the mandelate pathway by Pseudomonas putida. J Bacteriol 1996; 91: 1140–1154
  • Kaluzna I, Andrew AA, Bonilla M, Martzen MR, Stewart JD. Enantioselective reductions of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae dehydrogenases. J Mol Catal B Enzym 2002; 17: 101–105
  • Lacerda PSB, Ribeiro JB, Leite SGF, Coelho RB, Lima ELS, Antunes OAC. Microbial enantioselective reduction of ethyl-2-oxo-4-phenyl-butanoate. Biochem Eng J 2006a; 28: 299–302
  • Lacerda PSB, Ribeiro JB, Leite SGF, Ferrara MA, Coelho RB, Bon EPS, Lima ELS, Antunes OAC. Microbial reduction of ethyl 2-oxo-4-phenylbutyrate. Searching for R-enantioselectivity. New access to the enalapril like ACE inhibitors. Tetrahedron Asymm 2006b; 17: 1186–1188
  • Li YN, Shi XA, Zong MH, Meng C, Dong YQ, Guo YH. Asymmetric reduction of 2-octanone in water/organic solvent biphasic system with Baker's yeast FD-12. Enzyme Microb Technol 2007; 40: 1305–1311
  • Lou WY, Zong MH, Fan XD, Lu JQ, Du W. Asymmetric microbial reduction of organosilyl ketone with immobilized Saccharomyces cerevisiae cells in water/organic solvent biphasic system. Prog Biochem Biophys 2002; 29: 297–301
  • Nakamura K, Kondo S, Kawai Y, Ohno A. Stereochemical control in microbial reduction. XXI. Effect of organic solvent on reduction of α-keto esters mediated by bakers’ yeast. Bull Chem Soc Jpn 1993; 66: 2738–2743
  • Nakamura K, Kinoshita M, Ohno A. Structure of solvent affects enantioselectivity of lipase-catalyzed transesterification. Tetrahedron 1995a; 51: 8799–8808
  • Nakamura K, Kondo S, Nakajima N, Ohno A. Mechanistic study for stereochemical control of microbial reduction of α-keto esters in an organic solvent. Tetrahedron 1995b; 51: 687–694
  • Oda S, Kikuchi Y, Nanishi Y. Synthesis of optically active mandelic acid via microbial oxidation of racemic 1-phenyl-1,2-ethanediol. Biosci Biotechnol Biochem 1992; 56: 1216–1220
  • Oda S, Inada Y, Kobayashi A, 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 1998; 62: 1762–1767
  • Ramos JL, Duque E, Gallegos MT, Godoy P, Romos ML, Rojas A, Terán W, Segura A. Mechanisms of solvent tolerance in gram-negative bacteria. Annu Rev Microbiol 2002; 56: 743–768
  • Sheldon RA. Chirotechnology: Industrial synthesis of optically active compounds. Marcel Dekker Inc, New York 1993; 362–367
  • Shi YG, Fang Y, Jiang N, Xia YM. Enantioselective synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate mediated by Saccharomyces cerevisiae in organic solvents. J Food Sci Biotechnol (Chin) 2006a; 25: 66–73
  • Shi YG, Fang Y, Jiang N, Xia YM. Synthesis of chiral ethyl-2-oxo-4-phenylbutyrate catalyzed by Saccharomyces cerevisiae in aqueous phase. Chem Res App (Chin) 2006b; 18: 426–430
  • 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.
  • Shi YG, Fang Y, Ren YP, Wu HP, Guan HL. Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae. J Ind Microbiol Biotechnol 2008b; 35: 1419–1424
  • Turner JJ, Healy JP, Dobson RCJ, Gerrard JA, Hutton CA. Two new irreversible inhibitors of dihydrodipicolinate synthase. Bioorg Med Chem Lett 2005; 15: 995–998

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.