Enantioselective enzymes for organic synthesis created by directed evolution

Chemistry - A European Journal

Volumn 6, Issue 3, 2000, Pages 407-412

  Reetz, Manfred T ^a   Jaeger, Karl Erich ^b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Asymmetric catalysis; Directed evolution; Enzyme catalysis; High throughput screening; Mutagenesis

Indexed keywords

ENZYME; ESTER; ORGANIC COMPOUND; TRIACYLGLYCEROL LIPASE;

CATALYSIS; DIRECTED MOLECULAR EVOLUTION; ENZYME SYNTHESIS; GENE EXPRESSION; GENE EXPRESSION REGULATION; GENE LIBRARY; HYDROLYSIS; METHODOLOGY; MOLECULAR BIOLOGY; MUTAGENESIS; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; DIRECTED MOLECULAR EVOLUTION; ENZYMES; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE LIBRARY; MUTAGENESIS; STEREOISOMERISM;

EID: 0034603040     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000204)6:3<407::aid-chem407>3.3.co;2-p     Document Type: Article

References (66)

1. a) Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds (Eds.: A. N. Collins, G. N. Sheldrake, J. Crosby), Wiley, Chichester, 1992;
2. b) Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically Active Compounds (Eds.: A. N. Collins, G. N. Sheldrake, J. Crosby), Wiley, Chichester, 1997;
3. c) R. A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Dekker, New York, 1993.
4. a) Comprehensive Asymmetric Catalysis, Vol. I-III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
5. b) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, Vol. I-II, VCH, Weinheim, 1993;
6. c) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
7. d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993.
8. a) H. G. Davies, R. H. Green, D. R. Kelly, S. M. Roberts, Biotransformations in Preparative Organic Chemistry: The Use of Isolated Enzymes and Whole Cell Systems in Synthesis, Academic Press, London, 1989;
9. b) C. H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994;
10. c) Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), VCH, Weinheim, 1995;
11. d) K. Faber, Biotransformations in Organic Chemistry, 3rd ed., Springer, Berlin, 1997.
12. a) E. N. Jacobsen, N. S. Finney, Chem. Biol. 1994, 1, 85-90;
13. b) M. T. Reetz, Adv. Mater. 1997, 9, 943-954.
14. A. M. Klibanov, Trends Biotechnol. 1997, 15, 97-101.
15. R. S. Rogers, Chem. Eng. News 1999 (July 19), 87-91.
16. See for example: a) A. R. Fersht, Biochemistry 1987, 26, 8031-8037;
17. b) P. N. Bryan, Biotechnol. Adv. 1987, 5, 221-234;
18. c) J. A. Gerlt, Chem. Rev. 1987, 87, 1079-1105;
19. d) J. R. Knowles, Science 1987, 236, 1252-1258;
20. e) S. J. Benkovic, C. A. Fierke, A. M. Naylor, Science 1988, 239, 1105-1110;
21. f) J. A. Wells, D. A. Estell, Trends Biochem. Sci. 1988, 13, 291-297;
22. g) Y. Hirose, K. Kariya, Y. Nakanishi, Y. Kurono, K. Achiwa, Tetrahedron Lett. 1995, 36, 1063-1066;
23. h) Z. Shao, F. H. Arnold, Curr. Opin. Struct. Biol. 1996, 6, 513-518.
24. M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832.
25. M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832.
26. a) For the application of three-dimensional structural information as a guide to protein engineering by using genetic selection, see: P. Kast, D. Hilvert, Curr. Opin. Struct. Biol. 1997, 7, 470-479;
27. b) see also review concerning the creation of new molecular functions: D. R. Liu, P. G. Schultz, Angew. Chem. 1999, 111, 36-56; Angew. Chem. Int. Ed. 1999, 38, 36-54;
28. b) see also review concerning the creation of new molecular functions: D. R. Liu, P. G. Schultz, Angew. Chem. 1999, 111, 36-56; Angew. Chem. Int. Ed. 1999, 38, 36-54;
29. c) catalytic antibodies: P. G. Schultz, R. A. Lerner, Science 1995, 269, 1835-1842.
30. a) D. W. Leung, E. Chen, D. V. Goeddel, Technique 1989, 1, 11-15;
31. see also: b) K. A. Eckert, T. A. Kunkel, PCR Methods Appl. 1991, 1, 17-24;
32. c) R. C. Cadwell, G. F. Joyce, PCR Methods Appl. 1994, 3, S136-S140.
33. a) W. P. C. Stemmer, Nature 1994, 370, 389-391;
34. b) P. A. Patten, R. J. Howard, W. P. C. Stemmer, Curr. Opin. Biotechnol. 1997, 8, 724-733.
35. H. Zhao, L. Giver, Z. Shao, J. A. Affholter, F. H. Arnold, Nat. Biotechnol. 1998, 16, 258-261.
36. Z. Shao, H. Zhao, L. Giver, F. H. Arnold, Nucleic Acids Res. 1998, 26, 681-683.
37. a) J. Affholter, F. H. Arnold, CHEMTECH 1999, 29, 34-39; F. H. Arnold, Acc. Chem. Res. 1998, 31, 125-131.
38. a) J. Affholter, F. H. Arnold, CHEMTECH 1999, 29, 34-39; F. H. Arnold, Acc. Chem. Res. 1998, 31, 125-131.
39. M. T. Reetz, K.-E. Jaeger, Top. Curr. Chem. 1999, 200, 31-57.
40. a) M. T. Reetz, K.-E. Jaeger, Chem. Phys. Lipids 1998, 93, 3-14;
41. b) K.-E. Jaeger, B. W. Dijkstra, M. T. Reetz, Annu. Rev. Microbiol. 1999, 53, 315-351.
42. K. Liebeton, A. Zonta, K. Schimossek, M. Nardini, D. Lang, B. W. Dijkstra, M. T. Reetz, K.-E. Jaeger, unpublished results.
43. a) M. Eigen, R. Winkler-Oswatitisch, Steps towards Life: A Perspective on Evolution, Oxford University Press, Oxford, 1996;
44. b) J. M. Smith, E. Szathmáry, The Major Transitions in Evolution, Freeman/ Spektrum, Oxford, 1995.
45. J. E. Ness, M. Welch, L. Giver, M. Bueno, J. R. Cherry, T. V. Borchert, W. P. C. Stemmer, J. Minshull, Nat. Biotechnol. 1999, 17, 893-896.
46. M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650.
47. M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650.
48. M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stöckigt, Angew. Chem. 1999, 111, 1872-1875; Angew. Chem. Int. Ed. 1999, 38, 1758-1761.
49. M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stöckigt, Angew. Chem. 1999, 111, 1872-1875; Angew. Chem. Int. Ed. 1999, 38, 1758-1761.
50. M. Nardini, D. Lang, K.-E. Jaeger, B. W. Dijkstra, unpublished results.
51. M. T. Reetz, K.-E. Jaeger, A. Zonta, K. Schimossek, K. Liebeton (patent applied for with Studiengesellschaft Kohle mbH), DE-A 19731990.4, 1997 [Chem. Abs. 1999, 130, 149 528].
52. B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532.
53. B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532.
54. a) L. E. Janes, A. C. Löwendahl, R. J. Kazlauskas, Chem. Eur. J. 1998, 4, 2324-2331;
55. b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501;
56. b) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501;
57. c) G. Klein, J.-L. Reymond, Helv. Chim. Acta 1999, 82, 400-406;
58. d) J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758.
59. d) J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758.
60. a) P. Forrer, S. Jung, A. Plückthun, Curr. Opin. Struct. Biol. 1999, 9, 514-520;
61. b) J. Fastrez, Mol. Biotechnol. 1997, 7, 37-55.
62. a) In a brief report, random mutagenesis was used to improve the enantioselectivity of a transaminase from an ee value of 65 % to 98 % by creating a single mutant library, an evolutionary process not being necessary: X. Zhu, C. M. Lewis, M. C. Haley, M. B. Bhatia, S. Pannuri, S. Kamat, W. Wu, A. R. S. T. G. Bowen, poster and abstract at 2nd Annual Symposium on Exploiting Enzyme Technology for Industrial Applications; 20-21 February 1997, San Diego USA;
63. b) An esterase from Pseudomonas fluorescens was evolved in one step resulting in an ee value of 25 % in the synthesis of an epothilon building block: U. T. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559;
64. c) At the 37th IUPAC Congress in Berlin (18.08.99) Prof. C.-H. Wong presented a lecture in which he briefly mentioned the directed evolution of an aldolase for an enantioselective aldol addition.
65. A logical starting point in the quest to evolve enzymes as catalysts for enantioselective Diels - Alder reactions is with lipases, since the socalled acyl-enzyme intermediates, as in the case of acrylic acid, undergo H-bonding with the carbonyl function which induces activation through lowering of the LUMO.
66. M. Famulok, A. Jenne, Top. Curr. Chem. 1999, 202, 101-131.