New inhibitors of cysteine proteinases. Peptidyl acyloxymethyl ketones and the quiescent nucleofuge strategy

Journal of the American Chemical Society

Volumn 110, Issue 13, 1988, Pages 4429-4431

  Smith, Roger A ^a   Copp, Leslie J ^a   Coles, Peter J ^a   Robinson, Valerie J ^a   Heard, Stephen B ^a   Krantz, Allen ^a   Pauls, Henry W ^b   Spencer, Robin W ^c  

^a BioSci Research Canada Ltd   (Canada)

^b NPS Pharmaceutical Inc   (United States)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845278829     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00221a062     Document Type: Article

References (16)

1. Barrett, A. J.; Kirschke, H. Methods Enzymol. 1981, 80, 535–561.
2. Rich, D. H. In Proteinase Inhibitors; Barrett, A. J., Salvesen, G., Eds.; Elsevier: New York, 1986; pp 153–178.
3. Shaw, E. In Enzyme Inhibitors as Drugs; Sandler, M., Ed.; University Park Press: Baltimore, MD, 1980; pp 25–42.
4. Shaw, E.; Kettner, C. Acta Biol. Med. Ger. 1981, 40, 1503–1511. (b) Leary, R.; Larsen, D.; Watanabe, H.; Shaw, E. Biochemistry 1977, 16, 5857–5861.
5. Rasnick, D. Anal. Biochem. 1985, 149, 461–465. (b) Rauber, P.; Angliker, H.; Walker, B.; Shaw, E. Biochem. J. 1986, 238, 633–640. (c) Shaw, E.; Angliker, H.; Rauber, P.; Walker, B.; Wikstrom, P. Biomed. Biochem. Acta 1986, 45, 1397–1403.
6. Mathieu, J.; Allais, A.; Valls, J. Angew. Chem. 1960, 72, 71–74.
7. Clark, J. H.; Miller, J. M. Tetrahedron Lett. 1977, 599–602.
8. Green, G. D. J.; Shaw, E. J. Biol. Chem. 1981, 256, 1923–1928. (b) Ruscica, J.; Shaw, E. J. Biol. Chem. 1968, 243, 6312–6313.
9. Goering, H. L.; Rubin, T.; Newman, M. S. J. Am. Chem. Soc. 1954, 76, 787–791.
10. Bajkowski, A. S.; Frankfater, A. J. Biol. Chem. 1983, 258, 1645–1649.
11. Cleland, W. W. Methods Enzymol. 1979, 63, 103–138.
12. Serjeant, E. P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solution; Pergamon Press: NY, 1979.
13. Baici, A.; Gyger-Marazzi, M. Eur. J. Biochem. 1982, 129, 33–41.
14. Powers, J. C.; Gupton, B. F.; Harley, A. D.; Nishino, N.; Whitley, R. J. Biochim. Biophys. Acta 1977, 485, 156–166.
15. Takio, K.; Towatari, T.; Katanuma, N.; Teller, D. C.; Titani, K. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 3666–3670.
16. Drenth, J.; Kalk, K. H.; Swen, H. M. Biochemistry 1976, 15, 3731–3738.