Organic transformations catalyzed by engineered yeast cells and related systems

Current Opinion in Biotechnology

Volumn 11, Issue 4, 2000, Pages 363-368

  Stewart, Jon D ^a  

^a Univ of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANIC COMPOUND; UNSPECIFIC MONOOXYGENASE;

CATALYSIS; GENE SEQUENCE; GENETIC ENGINEERING; OXIDATION; PRIORITY JOURNAL; REDUCTION; REVIEW; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; YEAST;

BACTERIA (MICROORGANISMS); SACCHAROMYCES CEREVISIAE;

EID: 0033890961     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(00)00111-7     Document Type: Review

References (43)

1. Neuberg C. Biochemical reductions at the expense of sugars. Adv Carb Chem. 4:1949;75-117.
2. Servi S. Baker's yeast as a reagent in organic synthesis. Synthesis. 1990;1-25.
3. D'Arrigo P., Pedrocchi-Fantoni G., Servi S. Old and new synthetic capacities of baker's yeast. Adv Appl Microbiol. 44:1997;81-123.
4. Sybesma W.F.H., Straathof A.J.J., Jongejan J.A., Pronk J.T., Heignen J.J. Reductions of 3-oxo esters by baker's yeast: current status. Biocatal Biotrans. 16:1998;95-134.
5. Ema T., Sugiyama Y., Fukumoto M., Moriya H., Cui J-N., Sakai T., Utaka M. Highly enantioselective reduction of carbonyl compounds using a reductase purified from baker's yeast. J Org Chem. 63:1998;4996-5000.
6. Stewart J.D., Rodriguez S., Kayser M.M. Cloning, structure and activity of ketone reductases from baker's yeast. Kirst H.A., Yeh W-K., Zmijewski M.J. Enzyme Technologies for Pharmaceutical and Biotechnological Applications. 2000;Marcel Dekker, New York. in press. This chapter includes a systematic examination of the complete S. cerevisiae genome that attempts to answer the question: how many potential carbonyl reductases could be produced by baker's yeast?
7. Dahl A.C., Madsen J.Ø. Baker's yeast production of D- and L-3-hydroxy esters. Tetrahedron - Asymmetry. 9:1998;4395-4417.
8. Dao D.H., Okamura M., Akasaka T., Kawai Y., Hida K., Ohno A. Stereochemical control in microbial reduction. Part 31: reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions. Tetrahedron - Asymmetry. 9:1998;2725-2737.
9. Hayakawa R., Nozawa K., Shimizu M., Fujisawa T. Control of enantioselectivity in the baker's yeast reduction of β-keto ester derivatives in the presence of a sulfur compound. Tetrahedron Lett. 1998;67-70.
10. Anderson B.A., Hansen M.M., Harkness A.R., Henry C.L., Vicenzi J.T., Zmijewski M.J. Application of a practical biocatalytic reduction to an enantioselective synthesis of the 5H-2,3-benzodiazepine LY300164. J Am Chem Soc. 117:1995;12 358-12 359.
11. Sih C.J., Chen C-S. Microbial asymmetric catalysis - enantioselective reduction of ketones. Ang Chem Int Ed Engl. 23:1984;570-578.
12. D'Arrigo P., Fuganti C., Pedrocchi-Fantoni G., Servi S. Extractive biocatalysis: a powerful tool in selectivity control in yeast biotransformations. Tetrahedron. 54:1998;15 017-15 026.
13. D'Arrigo P., Lattanzio M., Fantoni G.P., Servi S. Chemo-enzymatic synthesis of the active enantiomer of the anorressant 2-benzylmorpholine. Tetrahedron - Asymmetry. 9:1998;4021-4026.
14. Shieh W-R., Gopalin A.S., 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.
15. Kayser M.M., Mihovilovic M.D., Kearns J., Feicht A., Stewart J.D. Baker's yeast-mediated reductions of α-keto esters and an α-keto-β-lactam. Two routes to the Paclitaxel sidechain. J Org Chem. 64:1999;6603-6608.
16. Ross-Macdonald P., Coelho P.S.R., Roemer T., Agarwal S., Kumar A., Jansen R., Cheung K-H., Sheehan A., Symoniatis D., Ummansky L.et al. Large-scale analysis of the yeast genome by transposon tagging and gene disruption. Nature. 402:1999;413-418. This project will provide an extremely useful resource for workers wishing to improve yeast-mediated reductions by gene knockout strategies. All of the yeast strains created by this project are available ( http://ycmi.med.yale.edu/YGAC/home.html) .
17. Winzeler A.E., Shoemaker D.D., Astromoff A., Liang H., Anderson K., Andre B., Bangham R., Benito R., Boeke J.D., Bussey H.et al. Functional characterization of the S. cerevisiae genome by gene deletion and parallel analysis. Science. 285:1999;901-906. This group is pursuing a different strategy with the same aim as in the previous reference: the creation of a library of S. cerevisiae strains that covers deletions of every open reading frame. Strains prepared by this group can be ordered ( http://www-sequence.stanford.edu/group/yeast_deletion_project/deletions3.html) .
18. Proteome Database on World Wide Web URL http://www.proteome.com/databases/index.html .
19. Rodriguez S., Kayser M.M., Stewart J.D. Improving the stereoselectivity of baker's yeast reductions by genetic engineering. Org Lett. 1:1999;1153-1155. This paper describes the first use of recombinant DNA technology specifically aimed at improving the stereoselectivity of yeast-mediated reductions.
20. Hajji K., Clotet J., Arino J. Disruption and phenotypic analysis of seven ORFs from the left arm of chromosome XV of Saccharomyces cerevisiae. Yeast. 15:1999;435-441.
21. Rodriguez Giordano, S. Baker's yeast β-keto ester reductions: whole cell biocatalysts with improved stereoselectivity by recombinant DNA techniques [PhD thesis]. Gainesville, FL: University of Florida; 2000.
22. Miya H., Kawada M., Sugiyama Y. Stereoselective reduction of ethyl 2-methyl-3-oxobutanoate by bacteria. Biosci Biotechnol Biochem. 60:1996;95-98.
23. Rodriguez S., Schroeder K.T., Kayser M.M., Stewart J.D. Asymmetric synthesis of β-hydroxy esters and α-alkyl-β-hydroxy esters by recombinant Escherichia coli expressing enzymes from baker's yeast. J Org Chem. 65:2000;2586-2587. These results demonstrate the feasibility of using whole E. coli cells expressing yeast reductases as a biocatalyst for asymmetric ketone reductions. This strategy avoids competition by other yeast reductases.
24. Kita K., Matsuzaki K., Hashimoto T., Yanase H., Kato N., Chung M.C-M., Kataoka M., Shimizu S. Cloning of the aldehyde reductase gene from a red yeast, Sporobolomyces salmonicolor, and characterization of the gene and its product. Appl Environ Microbiol. 62:1996;2303-2310.
25. Kita K., Fukura T., Nakase K-I., Okamoto K., Yanase H., Kataoka M., Shimizu S. Cloning, overexpression, and mutagenesis of the Sporobolomyces salmonicolor AKU4429 gene encoding a new aldehyde reductase, which catalyzes the stereoselective reduction of ethyl 4-chloro-3-oxobutanoate to ethyl (S)-4-chloro-3-hydroxybutanoate. Appl Environ Microbiol. 65:1999;5207-5211.
26. Nakamura K., Kawai Y., Nakajima N., 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.
27. Kataoka M., Rohani L.P.S., Yamamoto K., Wada M., Kawabata H., Kita K., Yanase H., Shimizu S. Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate: asymmetric reduction of ethyl-4-chloro-3-oxobutanoate by an Escherichia coli transformant expressing the aldehyde reductase gene from yeast. Appl Microbiol Biotechnol. 48:1997;699-703.
28. Kataoka M., Rohani L.P.S., Wada M., Kita K., Yanase H., Urabe I., Shimizu S. Escherichia coli transformant expressing the glucose dehydrogenase gene from Bacillus megaterium as a cofactor regenerator in a chiral alcohol production system. Biosci Biotechnol Biochem. 62:1998;167-169.
29. Kataoka M., Yamamoto K., Kawabata H., Wada M., Kita K., Yanase H., Shimizu S. Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by Escherichia coli transformant cells coexpressing the aldehyde reductase and glucose dehydrogenase genes. Appl Microbiol Biotechnol. 51:1999;486-490. The process described in the previous two references was simplified even further by co-expressing both the reductase and the cofactor regeneration enzyme in the same E. coli strain. This allowed a single cell type to be used in the bioconversion, and the method should be a useful model for other types of asymmetric reductions.
30. Wada M., Kataoka M., Kawabata H., Yasohara Y., Kizaki N., Hasegawa J., Shimizu S. Purification and characterization of NADPH-dependent carbonyl reductase, involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate, from Candida magnoliae. Biosci Biotechnol Biochem. 62:1998;280-285.
31. Wada M., Kawabata H., Kataoka M., Yasohara Y., Kizaki N., Hasegawa J., Shimizu S. Purification and characterization of an aldehyde reductase from Candida magnoliae. J Mol Catal B: Enzymatic. 6:1999;333-339.
32. Eugster H-P., Senstag C. Saccharomyces cerevisiae: an alternative source for human microsomal liver enzymes and its use in drug interaction studies. Toxicology. 82:1993;61-73.
33. Renaud J.P., Peyronneau M.A., Urban P., Truan G., Cullin C., Pompon D., Beaune P., Mansuy D. Recombinant yeast in drug metabolism. Toxicology. 82:1993;39-52.
34. Stewart J.D. Cyclohexanone monooxygenase: a useful reagent for asymmetric Baeyer-Villiger reactions. Curr Org Chem. 2:1998;211-232.
35. Trudgill P.W. Microbial degradation of the alicyclic ring. Structural relationships and metabolic pathways. Gibson D.T. Microbial Degradation of Organic Compounds. 1984;131-180 Marcel Dekker, New York. [Laskin AI, Mateles RI (Series editors): Microbiology Series, vol 13.].
36. Rissom S., Schwarlinek U., Vogel M., Tishkov V.I., Kragl U. Synthesis of chiral ε-lactones in a 2-enzyme system of cyclohexanone monooxygenase and formate dehydrogenase with integrating bubble-free-aeration. Tetrahedron - Asymmetry. 8:1997;2523-2526.
37. Stewart J.D., Reed K.W., Kayser M.M. 'Designer yeast': a new reagent for enantioselective Baeyer-Villiger oxidations. J Chem Soc Perkin Trans 1. 1996;755-757.
38. Stewart J.D., Reed K.W., Zhu J., Chen G., Kayser M.M. A 'designer yeast' that catalyzes the kinetic resolutions of 2-alkyl-substituted cyclohexanones by enantioselective Baeyer-Villiger oxidations. J Org Chem. 61:1996;7652-7653.
39. Stewart J.D., Reed K.W., Martinez C.A., Zhu J., Chen G., Kayser M.M. Recombinant baker's yeast as a whole-cell catalyst for asymmetric Baeyer-Villiger oxidations. J Am Chem Soc. 120:1998;3541-3548.
40. Kayser M.M., Chen G., Stewart J.D. Enantio- and regioselective Baeyer-Villiger oxidations of 2- and 3-substituted cyclopentanones using 'designer' oxidizing yeast. J Org Chem. 63:1998;7103-7106.
41. MacLeod R., Prosser H., Fikentscher L., Lanyi J., Mosher H.S. Asymmetric reductions. XII. Stereoselective ketone reductions by fermenting yeast. Biochemistry. 3:1964;838-846.
42. Ishihara K., Kondo S-I., Nakamura K., Nakajima N. Protein sequences of two keto ester reductases: possible identity as hypothetical proteins. Biosci Biotechnol Biochem. 60:1996;1538-1539.
43. Nakamura K., Kawai Y., Miyai T., Honda S., Nakajima N., Ohno A. Stereochemical control in microbial reduction. 18. Mechanism of stereocontrol in the diastereoselective reduction with baker's yeast. Bull Chem Soc Jpn. 64:1991;1467-1470.