Reactive-site design in folded-polypeptide catalysts - The leaving group pKa of reactive esters sets the stage for cooperativity in nucleophilic and general-acid catalysis

Chemistry - A European Journal

Volumn 6, Issue 12, 2000, Pages 2214-2220

  Nilsson, Jonas ^b   Baltzer, Lars ^a  

^a LINKÖPING UNIVERSITY   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Catalysts; De novo design; Helical structures; Histidine

Indexed keywords

ESTER; PEPTIDE; POLYPEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; KINETICS; MOLECULAR GENETICS; PH; PKA; PROTEIN FOLDING; PROTON TRANSPORT; REACTION ANALYSIS;

AMINO ACID SEQUENCE; CATALYSIS; ESTERS; HYDROLYSIS; KINETICS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN FOLDING;

EID: 0034674345     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000616)6:12<2214::aid-chem2214>3.3.co;2-5     Document Type: Article

References (32)

1. L. Baltzer, Top. Curr. Chem. 1999, 202, 39-76.
2. W. F. DeGrado, C. M. Summa, V. Pavone, F. Nastri, A. Lombardi, Ann. Rev. Biochem. 1999, 68, 779-819.
3. L. Brive, G. T. Dolphin, L. Baltzer, J. Am. Chem. Soc. 1997, 119, 8598-8607.
4. B. R. Hill, W. F. DeGrado, J. Am. Chem. Soc. 1998, 120, 1138-1145.
5. J. J. Skalicky, B. R. Gibney, F. Rabanal, R. J. Bieber Urbauer, P. L. Dutton, A. J. Wand, J. Am. Chem. Soc. 1999, 121, 4941-4951.
6. S. T. R. Walsh, H. Cheng, J. W. Bryson, H. Roder, W. F. DeGrado, Proc. Natl. Acad. Sci. USA 1999, 96, 5486-5491.
7. T. Kortemme, M. Ramirez-Alvarado, L. Serrano, Science 1998, 281, 253-256.
8. H. L. Schenck, S. H. Gellman, J. Am. Chem. Soc. 1998, 120, 4869-4870.
9. M. D. Struthers, R. P. Cheng, B. Imperiali, Science 1996, 271, 342-345.
10. B. I. Dahiyat, S. L. Mayo, Science 1997, 278, 82-87.
11. M. Mutter, S. Vuilleumier, Angew. Chem. 1989, 101, 551-692; Angew. Chem. Int. Ed. Engl. 1989, 28, 535-676.
12. M. Mutter, S. Vuilleumier, Angew. Chem. 1989, 101, 551-692; Angew. Chem. Int. Ed. Engl. 1989, 28, 535-676.
13. G. Tuchscherer, C. Lehmann, M. Mathieu, Angew. Chem. 1998, 110, 3160-3164; Angew. Chem. Int. Ed. 1998, 37, 2990-2993.
14. G. Tuchscherer, C. Lehmann, M. Mathieu, Angew. Chem. 1998, 110, 3160-3164; Angew. Chem. Int. Ed. 1998, 37, 2990-2993.
15. H. K. Rau, W. Haehnel, J. Am. Chem. Soc. 1998, 120, 468-476.
16. K. Johnsson, R. K. Allemann, H. Widmer, S. A. Benner, Nature (London) 1993, 365, 530-532.
17. K. Severin, H. D. Lee, A. J. Kennan, M. R. Ghadiri, Nature (London) 1997, 389, 706-709.
18. H. Kuang, M. D. Distefano, J. Am. Chem. Soc. 1998, 120, 1072-1073.
19. M. A. Shogren-Knaak, B. Imperiali, Bioorg. Med. Chem. 1999, 7, 1993-2002.
20. K. S. Broo, L. Brive, P. Ahlberg, L. Baltzer, J. Am. Chem. Soc. 1997, 119, 11362-11372.
21. K. Broo, L. Brive, A.-C. Lundh, P. Ahlberg, L. Baltzer, J. Am. Chem. Soc. 1996, 118, 8172-8173.
22. M. Allert, M. Kjellstrand, K. Broo, Å. Nilsson, L. Baltzer, J. Chem. Soc. Perkin Trans. 2 1998, 2271-2274.
23. M. Allert, L. Baltzer, unpublished results.
24. K. S. Broo, H. Nilsson, J. Nilsson, A. Flodherg, L. Baltzer, J. Am. Chem. Soc. 1998, 120, 4063-4068.
25. T. C. Bruice, R. Lapinski, J. Am. Chem. Soc. 1958, 80, 2265-2267.
26. L. Baltzer, K. S. Broo, H. Nilsson, J. Nilsson, Bioorg. Med. Chem. 1999, 7, 83-91.
27. S. Olofsson, G. Johansson, L. Baltzer, J. Chem. Soc. Perkin Trans. 2 1995, 2047-2056.
28. Y. H. Chen, J. T. Yang, K. H. Chau, Biochemistry 1974, 13, 3350-3359.
29. M. Engel, R. W. Williams, B. W. Erickson, Biochemistry 1991, 30, 3161-3169.
30. K. S. Broo, H. Nilsson, J. Nilsson, L. Baltzer, J. Am. Chem. Soc. 1998, 120, 10287-10295.
31. A. Fersht, Structure and Mechanism in Protein Science, 1999, W. H. Freeman and Company, New York.
32. M. Page, A. Williams, Organic and Bio-organic Mechanisms, 1997, Longman, Harlow, p. 259.