Application of combinatorial procedures in the search for serine- protease-like activity with focus on the acyl transfer step

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 145-148

  De Muynck, Hilde ^a   Madder, Annemieke ^a   Farcy, Nadia ^a   De Clercq, Pierre J ^a   Pérez Payán, M Nieves ^b   Öhberg, Liselotte M ^b   Davis, Anthony P ^b  

^a GHENT UNIVERSITY   (Belgium)

^b TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Combinatorial chemistry; Deconvolution; Serine proteases; Solid phase synthesis

Indexed keywords

AMINO ACID; ESTER DERIVATIVE; HEXAPEPTIDE; PEPTIDE LIBRARY; SERINE PROTEINASE;

AMINO ACID SEQUENCE; ARTICLE; ENZYME ACTIVITY; ENZYME ANALYSIS; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034598545     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<145::AID-ANIE145>3.0.CO;2-J     Document Type: Article

References (25)

1. Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758.
2. A. J. Kirby, Angew. Chem. 1996, 108, 770-740; Angew. Chem. Int. Ed. Engl. 1996, 35, 707-734.
3. A. J. Kirby, Angew. Chem. 1996, 108, 770-740; Angew. Chem. Int. Ed. Engl. 1996, 35, 707-734.
4. K. W. Hahn, W. A. Klis, J. M. Stewart, Science 1990, 248, 1544-1547.
5. For recent examples of artificial hydrolases not involving Ser, see a) J. Suh, S.S. Hah, J. Am. Chem. Soc. 1998, 120, 10088-10093;
6. b) L. Baltzer, K. S. Broo, H. Nilsson, J. Nilsson, Bioorg. Med. Chem. 1999, 7, 83-91.
7. A. Madder, P. J. De Clercq, J. Org. Chem. 1998, 63, 2548-2559.
8. For a recent combinatorial approach in the discovery of catalysts for phosphate hydrolysis, see D. A. Hérault, A. Berkessel, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105.
9. For a recent combinatorial approach in the discovery of catalysts for phosphate hydrolysis, see D. A. Hérault, A. Berkessel, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105.
10. D. M. Blow, Acc. Chem. Res. 1976, 9, 145-152.
11. J. F. Barry, A. P. Davis, M. N. Pérez-Payan, M. R. J. Elsegood, R. F. W. Jackson, C. Gennari, U. Piarulli, M. Gude, Tetrahedron Lett. 1999, 40, 2849-2852.
12. a) A. Furka, F. Sebestyen, M. Asgedom, G. Dibo, Int. J. Pept. Protein Res. 1991, 37, 487-493;
13. b) K. S. Lam, S. E. Salmon, E. M. Hersh, V. J. Hruby, W. M. Kazmierski, R. J. Knapp, Nature 1991, 354, 82-84;
14. c) R. A. Houghten, C. Pinila, S. E. Blondelle, J. R. Appel, C. T. Dooley, J. H. Cuervo, Nature 1991, 354, 84-86.
15. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
16. NF31 refers to Nadia Farcy, see A. Madder, N. Farcy, N. G. C. Hosten, H. De Muynck, P. J. De Clercq, J. Barry, A. P. Davis, Eur. J. Org. Chem. 1999, 11, 2787-2791.
17. 3CN).
18. a) E. Erb, K. D. Janda, S. Brenner, Proc. Natl. Acad. Sci. USA 1994, 91, 11 422-11 426;
19. b) S. M. Freier, D. A. M. Konings, J. R. Wyatt, D. J. Ecker, J. Med. Chem. 1995, 38, 344-352;
20. c) D. A. M. Konings, J. R. W. Wyatt, D. J. Ecker, S. M. Freier, J. Med. Chem. 1996, 39, 2710-2719;
21. d) L. Wilson-Lingardo, P. W. Davis, D. J. Ecker, N. Hébert, O. Acevedo, K. Sprankle, T. Brennan, L. Schwarcz, S. M. Freier, J. R. Wyatt, J. Med. Chem. 1996, 39, 2720-2726.
22. 50% cleavage of acetylimidazole is already observed in MeOH after 1 h at RT.
23. S. C. Zimmerman, J. S. Korthals, K. D. Cramer, Tetrahedron 1991, 47, 2649-2660.
24. The mechanism for the hydrolysis of p-nitrophenyl esters by serine proteases is still under discussion, see a) D. M. Quinn, J. P. Elrod, R. Ardis, P. Friesen, R. L. Schowen, J. Am. Chem. Soc. 1980, 102, 5358-5365;
25. b) R. A. Hess, A. C. Hengge, W. W. Cleland, J. Am. Chem. Soc. 1998, 120, 2703-2709.