2-aroylbenzoyl serine proteases: Photoreversible inhibition or photoaffinity labeling?

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2753-2761

  Jones, Paul B ^a   Porter, Ned A ^b  

^a DUKE UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 GUANIDINOPHENYL 2 BENZOYLBENZOATE; 4 NITROPHENYL 2 AROYLBENZOATE; BLOOD CLOTTING FACTOR 10; CHYMOTRYPSIN; PROTEINASE INHIBITOR; THROMBIN; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ENZYME ACTIVITY; ENZYME STABILITY; IRRADIATION; PHOTOACTIVATION; PHOTOAFFINITY LABELING; PHOTOCHEMISTRY; PROTEINASE INHIBITION; SYNTHESIS;

EID: 0033620441     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9842518     Document Type: Article

References (38)

1. Blank, M.; Soo, L. M.; Wasserman, N. H.; Erlanger, B. F. Science 1981, 214, 70-72.
2. Takeshita, M.; Irie, M. Tetrahedron Lett. 1998, 39, 613-616.
3. (a) Willner, I.; Rubin, S.; Wonner, J.; Effenberger, F.; Bauerle, P. J. Am. Chem. Soc. 1992, 114, 3150-3151.
4. (b) for a review see: Willner, I.; Rubin, S., Angew. Chem., Int. Ed. Engl. 1996, 35, 367-385.
5. Willner, I.; Rubin, S.; Riklin, A. J. Am. Chem. Soc. 1991, 113, 3321-3325.
6. For a review, see: Porter, N. A.; Bruhnke, J. D.; Koenigs, P. Biological Applications of Photochemical Switches; Morrison, H., Ed.; John Wiley and Sons: New York, 1993; Vol. II, Chapter 4, pp 197-242.
7. (a) Turner, A. D. Ph.D. Thesis, Duke University, 1986.
8. (b) Turner, A. D.; Monroe, D. M.; Roberts, H. R.; Porter, N. A.; Pizzo, S. V. Biochemistry 1986, 25, 4929.
9. (c) Turner, A. D.; Pizzo, S. V.; Rozakis, G. W.; Porter, N. A. J. Am. Chem. Soc. 1987, 109, 1274.
10. (d) Turner, A. D.; Pizzo, S. V.; Rozakis, G. W.; Porter, N. A. J. Am. Chem. Soc. 1988, 110, 244.
11. Bruhnke, J. D. Ph.D. Thesis Duke University, 1990.
12. Koenigs, P. Ph.D. Thesis Duke University, 1993.
13. Porter, N. A.; Bush, K. A.; Kinter, K. S. J. Photochem. Photobiol., B 1997, 38, 61.
14. Porter, N. A.; Bruhnke, J. D. U.S. Patent 5,114,851, 1993.
15. Arroyo, J. G.; Jones, P. B.; Porter, N. A.; Hatchell, D. L. Thromb. Haemostasis 1997, 78, 791.
16. Jones, P. B.; Pollastri, M. P.; Porter, N. A. J. Org. Chem. 1996, 61, 9455.
17. 2) and acylchymotrypsin as Chymo-1 (phenyl).
18. Bhatt, M. V.; Rao, G. V.; Rao, K. S. J. Org. Chem. 1979, 44, 984.
19. Erlanger, B. F.; Kokowski, N.; Cohen, W. Arch. Biochem. Biophys. 1961, 95, 271.
20. (a) Wagner, P. J.; Chen, C.-P. J. Am. Chem. Soc. 1976, 98, 239.
21. (b) Wagner, P. J. Pure Appl. Chem. 1977, 49, 259.
22. (a) Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965.
23. (b) Wagner, P. J.; Wirz, J.; Haag, R. Helv. Chim. Acta 1977, 60, 2595.
24. For a review, see: Wagner, P. J.; Park, B. S. Organic Photochemistry: Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. XI, Chapter 4, pp 227-366.
25. Wagner, P. J.; Giri, B. P.; Scaiano, J. C.; Ward, D. L.; Gabe, E.; Lee, F. L. J. Am. Chem. Soc. 1985, 107, 5483.
26. Campbell, P.; Gioannini, T. L. Photochem. Photobiol. 1979, 29, 883.
27. Gioannini, T. L.; Campbell, P. Biochem. Biophys. Res. Commun. 1980, 96, 106.
28. Green, N. M. Adv. Protein Chem. 1975, 29, 85.
29. Green, N. M.; Toms, E. J. Biochem. J. 1973, 133, 687.
30. Guchait, R. B.; Polakis, S. E.; Dimroth, P.; Stoll, E.; Moss, J.; Lane, M. D. J. Biol. Chem. 1974, 249, 6633.
31. Henrickson, K. P.; Allen, S. H. G.; Maloy, W. L. Anal. Biochem. 1979, 94, 366.
32. Turro, N. J. Modern Molecular Photochemistry, University Science Books; Mill Valley, CA, 1991; pp 38-151, 153-195.
33. Wagner, P. J.; Truman, R. J.; Scaiano, J. C. J. Am. Chem. Soc. 1985, 107, 7093.
34. Russell, J.; Thomson, R. H. J. Chem. Soc. 1962, 3379.
35. Lagodzinski, K. Chem. Ber. 1895, 28, 117.
36. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Synth. Commun. 1993, 23, 1443.
37. Bargellini, G. Gazz. Chim. Ital. 1914, 441, 193.
38. Storrs, R. W.; Tropper, F. D.; Li, H. Y.; Song, C. K.; Kuniyoshi, J. K.; Sipkins, D. A.; Li, K. C. P.; Bednarski, M. D. J. Am. Chem. Soc. 1995, 117, 7301.