Reaction engineering studies on β-ketoester reductions with whole cells of recombinant Saccharomyces cerevisiae

Enzyme and Microbial Technology

Volumn 38, Issue 3-4, 2006, Pages 536-544

  Engelking, H ^a   Pfaller, R ^b   Wich, G ^b   Weuster Botz, D ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b Consortium für Elektrochemische Industrie GmbH ^*  (Germany)

Author keywords

(S) 3 Hydroxy 3 phenylpropionate; (S) 4 Chloro 3 hydroxybutanoate; Baker's yeast; Enantioselective; Genetic algorithm

Indexed keywords

CELLS; GENETIC ALGORITHMS; GLUCOSE; ORGANIC SOLVENTS; REACTION KINETICS; YEAST;

BAKER'S YEAST; ENANTIOSELECTIVE; KETOESTER;

ESTERS;

3 PHENYLHYDRACRYLIC ACID; 4 CHLORO 3 HYDROXYBUTANOIC ACID; ACETIC ACID DERIVATIVE; BENZENE DERIVATIVE; BETA OXOCARBOXYLIC ACID ESTER; BUTYRIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHYL 4 CHLOROACETIC ACID; ETHYLBENZOYLACETIC ACID; ORGANIC SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIOCATALYST; COMPARATIVE STUDY; CONTROLLED STUDY; DRY WEIGHT; ENANTIOSELECTIVITY; ENZYME ENGINEERING; FUNGAL STRAIN; GENETIC ALGORITHM; LIQUID; NONHUMAN; REACTION TIME; REDUCTION; SACCHAROMYCES CEREVISIAE; SCREENING TEST; STOCHASTIC MODEL; WHOLE CELL;

BACILLUS SUBTILIS; SACCHAROMYCES CEREVISIAE;

EID: 28844495378     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2005.07.007     Document Type: Article

References (21)

1. I. Chin-Joe, P.M. Nelisse, A.J.J. Straathof, J.A. Jongejan, J.T. Pronk, and J.J. Heijnen Hydrolytic activity in Baker's yeast limits the yield of asymmetric 3-oxo ester reduction Biotechnol Bioeng 69 2000 370 376
2. R.S. Pereira 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 64
3. S. Shimizu, M. Kataoka, and K. Kita Chiral alcohol synthesis with yeast carbonyl reductases J Mol Catal B 5 1998 321 325
4. M. Bertau How cell physiology affects enantioselectivity of the biotransformation of ethyl 4-chloro-acetoacetate with S. cerevisiae Biocatal Biotransform 20 2002 363 367
5. J.Y. Houng, H.F. Hsu, Y.H. Liu, and J.Y. Wu Applying the Tagouchi robust design to the optimization of the asymmetric reduction of ethyl 4-chloro acetoacetate by Bakers' yeast J Biotechnol 100 2003 239 250
6. O. Rotthaus, D. Krüger, M. Demuth, and K. Schaffner Reductions of keto esters with Baker's yeast in organic solvents - a comparison with the results in water Tetrahedron 53 1997 935 938
7. R. Chênevert, G. Fortier, and R.B. Rhalid Asymmetric synthesis of both enantiomers of fluoxetine via microbial reduction of ethyl benzoylacetate Tetrahedron 48 1992 6769 6776
8. H. Engelking, R. Pfaller, G. Wich, and D. Weuster-Botz Stereoselective reduction of ethyl 4-chloro acetoacetate with recombinant Pichia pastoris Tetrahedron - Asymm 15 2004 3591 3593
9. W.F.H. Sybesma, A.J.J. Straathof, and J.A. Jongejan Reductions of 3-oxo esters by Baker's yeast: current status Biocatal Biotransfor 1 1998 95 134
10. W.R. Shieh, A.S. Gopalan, and C.J. Sih Stereochemical control of yeast reductions. 5. Characterization of the oxidoreductases involved IN the reduction of ß-keto esters J Am Chem Soc 107 1985 2993 2994
11. P. Wenz, S. Schwank, U. Hoja, and H.J. Schüller A downstream regulatory element located within the coding sequence autoregulated expression of the yeast fatty acid gene FAS2 by the FAS1 gene product Nucl Acids Res 29 2001 4625 4632
12. N.W. Fadnavis, S.K. Vadivel, and U.T. Bhalerao Biotransformation with Baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β- ketoester reductions and carbon-carbon bond cleavages Tetrahedron - Asymm 8 1997 2355 2359
13. C. Medson, A.J. Smallridge, and M.A. Trewhella The stereoselective preparation of β-hydroxy esters using a yeast reduction in an organic solvent Tetrahedron - Asymm 8 1997 1049 1054
14. B. Zhou, A.S. Gopalan, F. VanMidlesworth, W.R. Shieh, and C.J. Sih Stereochemical control of yeast reductions. 1. Asymmetric synthesis of l-carnitin J Am Chem Soc 105 1983 5925 5926
15. E. Boccù, C. Ebert, L. Gardossi, T. Gianferrara, and P. Linda Chemometric optimization of an asymmetric reduction catalyzed by Baker's yeast Biotechnol Bioeng 35 1990 928 934
16. K. Nakamura, S. Kondo, Y. Kawai, and A. Ohno Stereochemical control in microbial reduction XXI. Effect of organic solvents on reduction of α-keto esters mediated by Bakers' yeast B Chem Soc Jpn 66 1993 2738 2743
17. K. Nakamura, K. Inoue, K. Ushio, S. Oka, and A. Ohno Effect of allyl alcohol on reduction of ß-keto esters by Bakers' yeast Chem Lett 9 1987 679 682
18. K. Ushio, J. Hada, Y. Tanaka, and K. Ebara Allyl bromide a powerful inhibitor against R-enzyme activities in Bakers' yeast reduction of ethyl 3-oxoalkanoates Enzyme Microb Technol 15 1993 222 228
19. D. Weuster-Botz Experimental design for fermentation media development: statistical design or global random search? J Biosci Bioeng 90 2000 473 483
20. L. Laouar, K.C. Lowe, and B.J. Mulligan Yeast responses to nonionic surfactants Enzyme Microb Technol 18 1996 733 738
21. M. Kataoka, K. Kita, M. Wada, Y. Yasohara, J. Hasegawa, and S. Shimizu Novel bioreduction system for production of chiral alcohols Appl Microbiol Biotechnol 62 2003 437 445