Noncovalent inhibition of the serine proteases, α-chymotrypsin and trypsin by trifluoro(organo)borates

Organic and Biomolecular Chemistry

Volumn 3, Issue 5, 2005, Pages 941-944

  Smoum, Reem ^a   Rubinstein, Abraham ^a   Srebnik, Morris ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMINO ACIDS; DERIVATIVES; ELECTROSTATICS; ENZYME INHIBITION; HYDROGEN BONDS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; POLYPEPTIDES; POTASSIUM COMPOUNDS;

Α-CHYMOTRYPSIN; POTASSIUM HYDROGEN DIFLUORIDE (KHF2); SERINE PROTEASE; TRANSITION-STATE INHIBITORS;

ENZYMES;

BORIC ACID; CHYMOTRYPSIN; CHYMOTRYPSIN A; FLUORINE; SERINE PROTEINASE; SERINE PROTEINASE INHIBITOR; TRYPSIN; TRYPSIN INHIBITOR;

ARTICLE; BINDING COMPETITION; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HYDROGEN BOND; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; SYNTHESIS;

BINDING SITES; BINDING, COMPETITIVE; BORATES; CHYMOTRYPSIN; FLUORINE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; SERINE ENDOPEPTIDASES; SERINE PROTEINASE INHIBITORS; TRYPSIN; TRYPSIN INHIBITORS;

TRIFLUORO;

EID: 15244358939     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415957h     Document Type: Article

References (37)

1. B. Walker and J. F. Lynas, Cell. Mol. Life Sci., 2001, 58, 596 and references therein.
2. D. Leung, G. Abbenante and D. P. Fairlie, J. Med. Chem., 2000, 43, 305.
3. R. Babin and S. L. Bender, Chem. Rev., 1997, 97, 1359.
4. H. U. Demuth, J. Enzyme Inhib., 1990, 3, 249.
5. J. C. Powers, J. L. Asgian, O. D. Ekici and K. E. James, Chem. Rev., 2002, 102, 4639.
6. P. E. J. Sanderson, Med. Res. Rev., 1999, 19, 179.
7. F. Al-Obeidi and J. A. Ostrem, Drug Discovery Today, 1998, 3, 223.
8. M. R. Wiley and M. J. Fisher, Expert Opin. Ther. Pat., 1997, 7, 1265.
9. J. P. Vacca, Curr. Opin. Chem. Biol., 2000, 4, 394.
10. K. Tomoo, K. Satoh, Y. Tsuda, K. Wanaka, S. Okamoto, A. Hijikata-Okunomiya, Y. Okada and T. Ishida, J. Biochem., 2001, 129, 455.
11. S. R. Presnell, G. S. Patil, C. Mura, K. M. Jude, J. M. Conley, J. A. Bertrand, C.-M. Kam, J. C. Powers and L. D. Williams, Biochemistry, 1998, 37, 17068.
12. (a) K. A. Koehler and G. E. Lienhard, Biochemistry, 1971, 10, 2477;
13. (b) R. V. Wolfenden, Acc. Chem. Res., 1972, 5, 10;
14. (c) G. E. Lienhard, Science, 1973, 180, 149;
15. (d) R. V. Wolfenden and A. Radzicka, Curr. Opin. Struct. Biol., 1991, 1, 780.
16. E. Tsilikounas, C. A. Kettner and W. W. Bachovchin, Biochemistry, 1992, 31, 12839.
17. W. W. Bachovchin, W. Y. L. Wong, S. Farr-Jones, A. B. Shenvi and C. A. Kettner, Biochemistry, 1988, 27, 7689.
18. (a) T. Ohba, E. Ikeda and H. Takei, Bioorg. Med. Chem., 1996, 6, 1875;
19. (b) A. Kashima, Y. Inove, S. Sugio, I. Maeda, T. Nose and Y. Shimoshigashi, Eur. J. Biochem., 1998, 255, 12;
20. (c) M. F. Paria and R. H. Abeles, Biochemistry, 1992, 31, 9429.
21. D. H. Kinder and J. A. Katzenellenbogen, J. Med. Chem., 1985, 28, 1917.
22. E. Vedejs, R. W. Chapman, S. C. Fields, S. Lin and M. R. Shrimpf, J. Org. Chem., 1995, 60, 3020 and references therein.
23. S. Darses, G. Michaud and J.-P. Genêt, Eur. J. Org. Chem., 1999, 1875.
24. H.-J. Frohn, H. Franke, P. Fritzen and V. V. Bardin, J. Organomet. Chem., 2000, 598, 127.
25. S. Darses and J.-P. Genêt, Eur. J. Org. Chem., 2003, 4313.
26. (a) J.-P. Tremblay-Morin, S. Raeppel and F. Gaudette, Tetrahedron Lett., 2004, 45, 3471;
27. (b) T. E. Barder and S. L. Buchwald, Org. Lett., 2004, 16, 1523.
28. M. Dixon, Biochem. J., 1953, 55, 170.
29. D. G. Gorenstein and D. O. Shah, Biochemistry, 1982, 21, 4679.
30. D. O. Shah and D. G. Gorenstein, Biochemistry, 1983, 22, 6096.
31. B. D. Sykes and J. H. Weiner, in Magnetic Resonance In Biology, ed. J. S. Cohen, Wiley, New York, 1980, vol. 1, p. 171.
32. J. T. Gerig, in Biochemical Magnetic resonance, ch. 5, eds. L. J. Berliner and J. Reuben, Plenum Press, New York, 1978.
33. A. Saika and C. P. Slichter, J. Chem. Phys., 1954, 22, 26.
34. M. Karplus and T. P. Das, J. Chem. Phys., 1961, 34, 1683.
35. M. Tsavalos, B. C. Nicholson and T. M. Spotswood, Aust. J. Chem., 1978, 31, 2179.
36. H. J. Knight, E. H. Williams and T. M. Spotswood, Aust. J. Chem., 1978, 31, 2187.
37. D. G. Gorenstein and D. O. Shah, Biochemistry, 1982, 21, 4679.