Directed evolution of an esterase from Pseudomonas fluorescens. Random mutagenesis by error-prone PCR or a mutator strain and identification of mutants showing enhanced enantioselectivity by a resorufin-based fluorescence assay

Biological Chemistry

Volumn 380, Issue 7-8, 1999, Pages 1029-1033

  Henke, Erik ^a   Bornscheuer, Uwe T ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Enantioselectivity; Error prone PCR; Esterase; High throughput screening; Mutator strain; Pseudomonas fluorescens; Resorufin

Indexed keywords

BACTERIAL ENZYME; ESTERASE; MUTANT PROTEIN; RESORUFIN;

ARTICLE; BACTERIAL GENE; CONTROLLED STUDY; DRUG HYDROLYSIS; ENZYME SPECIFICITY; ESCHERICHIA COLI; FLUORESCENCE ANALYSIS; MOLECULAR EVOLUTION; MUTAGENESIS; NONHUMAN; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS;

DIRECTED MOLECULAR EVOLUTION; ESTERASES; MUTAGENESIS; OXAZINES; POLYMERASE CHAIN REACTION; PSEUDOMONAS FLUORESCENS; SPECTROMETRY, FLUORESCENCE;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS FLUORESCENS;

EID: 0032853779     PISSN: 14316730     EISSN: None     Source Type: Journal    
DOI: 10.1515/BC.1999.128     Document Type: Article

References (26)

1. Amaki, Y., Tulin, E.E., Ueda, S., Ohmiya, K., and Yamane, T. (1992). Purification and properties of a thermostable esterase of Bacillus stearothermophilus produced by recombinant Bacillus brevis. Biosci. Biotech. Biochem. 56, 238-241.
2. Arnold, F.H. (1998). Design by directed evolution. Acc. Chem. Res. 31, 125-131.
3. Bornscheuer, U.T. (1998). Directed evolution of enzymes. Angew. Chem., Int. Ed. Engl. 37, 3105-3108.
4. Bornscheuer, U.T., Altenbuchner, J., and Meyer, H.H. (1998). Directed evolution of an esterase for the stereoselective resolution of a key intermediate in the synthesis of Epothilones. Biotechnol. Bioeng. 58, 554-559.
5. Bornscheuer, U.T., Altenbuchner, J., and Meyer, H.H. (1999). Directed evolution of an esterase: Screening of enzyme libraries based on pH-indicators and a growth assay. Bioorg. Med. Chem., in press.
6. Bornscheuer, U.T., and Kazlauskas, R.J. (1999). Hydrolases in Organic Synthesis - Regio- and Stereoselective Biotransformations. (Weinheim, Germany: Wiley-VCH).
7. Chen, C.S., Fujimoto, Y., Girdaukas, G., and Sih, C.J. (1982). Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104, 7294-7299.
8. Choi, K.D., Jeohn, G.H., Rhee, J.S., and Yoo, O.J. (1990). Cloning and nucleotide sequence of an esterase gene from Pseudomonas fluorescens and expression of the gene in Escherichia coli. Agric. Biol. Chem. 54, 2039-2045.
9. Faber, K. (1997). Biotransformations in Organic Chemistry. (Berlin: Springer).
10. Hecht, H.J., Sobek, H., Haag, T., Pfeifer, O., and Pée, K.H. v. (1994). The metal-ion-free oxidoreductase from Streptomyces aureofaciens has an α/β hydrolase fold. Nature Struct. Biol. 1, 532-537.
11. Hirose, Y., Kariya, K., Sasaki, I., Kurono, Y., Ebiike, H., and Achiwa, K. (1992). Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines. Tetrahedron Lett. 33, 7157-7160.
12. Kazlauskas, R.J., and Bornscheuer, U.T. (1998). Biotransformations with lipases. In: Biotechnology-Series, Vol. 8a, H.J. Rehm, G. Reed, A. Pühler, P.J.W. Stadler and D.R. Kelly, eds. (Weinheim, Germany: VCH-Wiley), pp. 37-191.
13. Khalameyzer, V., and Bornscheuer, U.T. (1999). Overexpression and characterization of an esterase from Streptomyces diastatochromogenes. Biotechnol. Lett. 21, 101-104.
14. Khalameyzer, V., Fischer, I., Bornscheuer, U.T., and Altenbuchner, J. (1999). Screening, nucleotide sequence and biochemical characterization of an esterase from Pseudomonas fluorescens with high activity toward lactones. Appl. Environm. Microbiol. 65, 477-482.
15. Krebsfänger, N., Schierholz, K., and Bornscheuer, U.T. (1998a). Enantioselectivity of a recombinant esterase from Pseudomonas fluorescens towards alcohols and carboxylic acids. J. Biotechnol. 60, 105-111.
16. Krebsfänger, N., Zocher, F., Altenbuchner, J., and Bornscheuer, U.T. (1998b). Characterization, and enantioselectivity of a recombinant esterase from Pseudomonas fluorescens. Enzyme Microb. Technol. 21, 641-646.
17. Leung, D.W., Chen, E., and Goeddel, D.V. (1989). A method for random mutagenesis of a defined DNA segment using a modified polymerase chain reaction. Technique 1, 11-15.
18. Pelletier, I., and Altenbuchner, J. (1995). A bacterial esterase is homologous with non-haem haloperoxidases and displays brominating activity. Microbiology 141, 459-468.
19. Phytian, S.J. (1998). Esterases. In: Biotechnology-Series, Vol. 8a, H.J. Rehm, G. Reed, A. Pühler, P.J.W. Stadler and D.R. Kelly, eds. (Weinheim, Germany: VCH-Wiley), pp. 193-241.
20. Reetz, M.T., and Jaeger, K.-E. (1999). Superior biocatalysts by directed evolution. Topic Curr. Chem. 200, 31-57.
21. Reetz, M.T., Zonta, A., Schimossek, K., Liebeton, K., and Jaeger, K.-E. (1997). Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution. Angew. Chem., Int. Ed. Engl. 36, 2830-2832.
22. Sakai, T., Kawabata, I., Kishimoto, T., Erna, T., and Utaka, M. (1997). Enhancement of the enantioselectivity in lipase-catalyzed kinetic resolutions of 3-phenyl-2H-azirine-2-methanol by lowering the temperature to -40 degree. J. Org. Chem. 62, 4906-4907.
23. Scheib, H., Pleiss, J., Stadler, P., Kovac, A., Potthof, A.P., Haalck, L., Spener, F., Paltauf, F., and Schmid, R.D. (1998). Rational design of Rhizopus oryzae lipase with modified stereoselectivity toward triradylglycerols. Protein Eng. 11, 675-682.
24. Stemmer, W.P.C. (1994). DNA shuffling by random fragmentation and reassembly: In vitro recombination for molecular evolution. Proc. Natl. Acad. Sci. USA 91, 10747-10751.
25. Stokes, T.M., and Oehlschlager, A.C. (1987). Enzyme reaction in apolar solvents: the resolution of (±)-sulcatol with porcine pancreatic lipase. Tetrahedron Lett. 28, 2091-2094.
26. Yang, H., Henke, E., and Bornscheuer, U.T. (1999). The use of vinyl esters significantly enhanced enantioselectivities and reaction rates in lipase-catalyzed resolutions of arlyaliphatic carboxylic acids. J. Org. Chem. 64, 1709-1712.