Enhancement of asymmetric bioreduction of ethyl 4-chloro acetoacetate by the design of composition of culture medium and reaction conditions

Process Biochemistry

Volumn 42, Issue 1, 2007, Pages 1-7

  Houng, Jer Yiing ^a   Liao, Jia Hong ^a   Wu, Jiumn Yih ^a   Shen, Szu Chuan ^a   Hsu, Hsia Fen ^a  

^a I SHOU UNIVERSITY   (Taiwan)

Author keywords

Asymmetric reduction; Culture medium composition; Desirability function; Steepest ascent method; Stereospecificity; Taguchi method

Indexed keywords

BIOMASS; CELL CULTURE; GLUCOSE; MALTOSE; PH EFFECTS; RATE CONSTANTS; REDUCTION; YEAST;

ASYMMETRIC REDUCTION; BIOREDUCTION; BUFFERS; CULTURE MEDIUM COMPOSITION; PEPTONE; STEREOSPECIFICITY;

ORGANIC COMPOUNDS;

EID: 33751054045     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2006.03.035     Document Type: Article

References (35)

1. Pereira R.S. The use of baker's yeast in the generation of asymmetric centers to produce chiral drugs and other compounds. Crit Rev Biotechnol 18 (1998) 25-83
2. D'Arrigo P., Pedrocchi-Fantoni G., and Servi S. Stereoselective synthesis of chiral compounds using whole-cell biocatalysts. Stereoselective biocatalysis (2000), Dekker, New York p. 365-96
3. Kataoka M., Kita K., Wada M., Yasohara Y., Hasegawa J., and Shimizu S. Novel bioreduction system for the production of chiral alcohols. Appl Microbiol Biotechnol 62 (2003) 437-445
4. Shieh E.R., Gopalan A.S., and Sih C.J. Stereochemical control of yeast reductions. 5. Characterization of the oxidoreductases involved in the reduction of β-keto esters. J Am Chem Soc 107 (1985) 2993-2994
5. Heidlas J., Engel K.H., and Tressl R. Purification and characterization of two oxidoreductases involved in the enantioselective reduction of 3-oxo, 4-oxo and 5-oxo esters in baker's yeast. Eur J Biochem 172 (1988) 633-639
6. Nakamura K., Kawai Y., Nakajima N., and Ohno A. Stereochemical control of microbial reduction. 17. A method for controlling the enantioselectivity of reductions with baker's yeast. J Org Chem 56 (1991) 4778-4783
7. Zhou B., Gopalan A.S., VanMiddlesworth F., Shieh W.R., and Sih C.J. Stereochemical control of yeast reduction. 1. Asymmetric synthesis of l-carnitine. J Am Chem Soc 105 (1983) 5925-5926
8. Nakamura K., Kawai O., Shinzaburo K.A., and Ohno A. A new method for stereochemical control of microbial reduction. Reduction of β-keto esters with baker's yeast immobilized by magnesium alginate. Tetrahedron Lett 27 (1989) 2245-2246
9. Nakamura K., Inoue K., Ushio K., Oka S., and Ohno A. Effect of allyl alcohol on reduction of β-esters by baker's yeast. Chem Lett (1987) 679-682
10. Ushio K., Hada J., Tanaka Y., and Ebara K. Allyl bromide, a powerful inhibitor against R-enzyme activities in baker's yeast reduction of ethyl 3-oxoalkanoates. Enzyme Microb Technol 15 (1993) 222-228
11. Nakamura K., Kondo S., Kawai Y., and Ohno A. Stereochemical control in microbial reduction. XXI. Effect of organic solvents on reduction of α-keto esters mediated by baker's yeast. Bull Chem Soc Jpn 66 (1993) 2738-2743
12. Rotthaus O., Kruger D., Demuth M., and Schaffner K. Reductions of keto esters with baker's yeast in organic solvents-a comparison with the results in water. Tetrahedron 53 (1997) 935-938
13. Chen J., Wang K.P., Houng J.Y., and Lee S.L. Design of the pH profile for asymmetric bioreduction of ethyl 4-chloro-3-oxobutyrate on the basis of a data-driven method. Biotechnol Prog 18 (2002) 1414-1422
14. Houng J.Y., Hsu H.F., Liu Y.H., and Wu J.Y. Applying the Taguchi robust design to the optimization of the asymmetric reduction of ethyl 4-chloro acetoacetate by bakers' yeast. J Biotechnol 100 (2003) 239-250
15. Houng J.Y., and Liau J.S. Applying slow-release biocatalysis to the asymmetric reduction of ethyl 4-chloro acetoacetate. Biotechnol Lett 25 (2003) 17-21
16. Katz M., Sarvary I., Frejd T., Hahn-Hägerdal B., and Gorwa-Grauslund M.F. An improved stereoselective reduction of a bicyclic diketone by Saccharomyces cerevisiae combining process optimization and strain engineering. Appl Microbiol Biotechnol 59 (2002) 641-648
17. Katz M., Frejd T., Hahn-Hägerdal B., and Gorwa-Grauslund M.F. Efficient anaerobic whole cell stereoselective bioreduction with recombinant Saccharomyces cerevisiae. Biotechnol Bioeng 84 (2003) 573-582
18. Dahl A.C., and Madsen J.Ø. Baker's yeast: production of d- and l-3-hydroxy esters. Tetrahedron Asymmetry 9 (1998) 4395-4417
19. Mu X.Q., Xu Y., Nie Y., Ouyang J., and Sun Z.H. Candida parapsilosis CCTCC M203011 and the optimization of fermentation medium for stereoinversion of (S)-1-phenyl-1,2-ethanediol. Process Biochem 40 (2005) 2345-2350
20. Patel R.N., McNamee C.G., Banerjee A., Howell J.M., Robison R.S., and Szarka L.J. Stereoselective reduction of β-keto esters by Geotrichum candidum. Enzyme Microb Technol 14 (1992) 731-738
21. Shimizu S., Kataoka M., and Kita K. Chiral alcohol synthesis with yeast carbonyl reductases. J Mol Catal B Enzym 5 (1998) 321-325
22. Cheng C., and Ma J.H. Enantioselective synthesis of S-(-)-1-phenylethanol in Candida utilis semi-fed-batch cultures. Process Biochem 31 (1996) 119-124
23. Harrington Jr. E.C. The desirability function. Ind Qual Control 21 (1965) 494-498
24. Derringer G., and Suich R. Simultaneous optimization of several response variables. J Qual Technol 12 (1980) 214-219
25. Elibol M. Optimization of medium composition for actinorhodin production by Streptomyces coelicolor A3(2) with response surface methodology. Process Biochem 39 (2004) 1057-1062
26. Abdel-Fattaha Y.R., Saeedb H.M., Goharc Y.M., and El-Bazb M.A. Improved production of Pseudomonas aeruginosa uricase by optimization of process parameters through statistical experimental designs. Process Biochem 40 (2005) 1707-1714
27. Rao R.S., Prakasham R.S., Prasad K.K., Rajesham S., Sarma P.N., and Rao L.V. Xylitol production by Candida sp.: parameter optimization using Taguchi approach. Process Biochem 39 (2004) 951-956
28. Stone R.A., and Veevers A. The Taguchi influence on designed experiments. J Chemometrics 8 (1994) 103-110
29. Jimenez L., Navarro E., Ferrer J.L., Lopez F., and Ariza J. Biobleaching of cellulose pulp from wheat straw with enzymes and hydrogen peroxide. Process Biochem 35 (1999) 149-157
30. Bocchini D.A., Alves-Prado H.F., Baida L.C., Roberto I.C., Gomes E., and Da Silva R. Optimization of xylanase production by Bacillus circulans D1 in submerged fermentation using response surface methodology. Process Biochem 38 (2002) 727-731
31. Taguchi G. System of experimental design. Engineering methods to optimize quality and minimize costs (1987), Kraus International Publications, New York
32. ® in technology and product development (1995), Addison-Wesley Publishing Company, New York
33. Box G.E.P., Hunter E.G., and Hunter J.S. Statistics for experimenters (1978), John Wiley and Sons, New York
34. 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
35. Bare G., Jacques P., Hubert J.B., Rikir R., and Thonart P. Bioconversion of an l-carnitine precursor in a one- or two-phase system. Appl Biochem Biotechnol 28/29 (1991) 445-456