Bifunctional peptide boronate inhibitors of thrombin: Crystallographic analysis of inhibition enhanced by linkage to an exosite 1 binding peptide

Biochemistry

Volumn 37, Issue 41, 1998, Pages 14420-14427

  Skordalakes, Emmanuel ^a   Elgendy, Said ^a   Goodwin, Christopher A ^a   Green, Donovan ^a   Scully, Michael F ^a   Kakkar, Vijay V ^a   Freyssinet, Jean Marie ^b   Dodson, Guy ^c   Deadman, John J ^a  

^a THROMBOSIS RESEARCH INSTITUTE   (United Kingdom)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; HIRUDIN; THROMBIN INHIBITOR;

ARTICLE; BINDING AFFINITY; COMPETITIVE INHIBITION; CRYSTALLOGRAPHY; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SPECIFICITY; GENETIC LINKAGE; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; ANTITHROMBINS; BORONIC ACIDS; CARRIER PROTEINS; CRYSTALLOGRAPHY, X-RAY; HIRUDINS; HUMANS; KINETICS; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; PEPTIDES; RECOMBINANT PROTEINS; THROMBIN;

EID: 0032514767     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi980225a     Document Type: Article

References (42)

1. Claeson, G. (1994) Blood Coagulation Fibrinolysis 5, 411-436.
2. Kettner, C., Mersinger, L., and Knabb, R. (1990) J. Biol. Chem. 265, 18289-18297.
3. Nienaber, V. L., Mersinger, L. J., and Kettner, C. A. (1996) Biochemistry 35, 9690-9699.
4. Maraganore, J. M., Bourdon, P., Jablonski, J., Ramachandran, K. L., and Fenton, J. W. (1990) Biochemistry 29, 7095-7087.
5. DiMaio, J., Gibbs, B., Munn, D., Lefebvre, J., Ni, F., and Konishi, Y. (1990) J. Biol. Chem. 265, 21698-21703.
6. DiMaio, J., Ni, F., and Konishi, Y. (1991) FEBS. Lett. 287, 47-52.
7. Matteson, D. S. (1995) Stereodirected Synthesis with Organoboranes, Chapter 1, pp 1-52, Springer-Verlag, Berlin-Heidelberg.
8. Deadman, J. J., Elgendy, S., Goodwin, C. A., Green, D., Baban, J. A., Patel, G., Skordalakes, E., Chino, N., Claeson, G., Kakkar, V. V., and Scully, M. F. (1995) J. Med. Chem. 38, 1511-1522.
9. Elgendy, S., Patel, G., Green, D., Goodwin, C. A., Scully, M. F., Husman, W., Skordalakes, E., Kakkar, V. V., and Deadman, J. J. (1997) Tetrahedron Lett. 38, 3305-3308.
10. Leatherbarrow, R. J. (1987) Enzfitter: A Non-Linear regression data Analysis program for IBM PC, Elsevier-Biosoft, Amsterdam, U.K.
11. Baici, A., and Gyger-Marazzi, M. (1982) Eur. J. Biochem 129, 33-41.
12. Otwinowski, Z., and Minor, W. (1993) in Data Collection and Processing (Sawyer, L., Isaacs, N., and Bailey, S., Eds.) pp 556-562, SERC Daresbury Laboratory, Warrington, U.K.
13. Skrzypczak-Jankun, E., Carperos, V. E., Ravichandran, K. G., and Tulinsky, A. (1991) J. Mol. Biol. 221, 1379-1393.
14. CCP4 (1994) Acta Crystallogr. D50, 760-763.
15. Banner, D. W., and Hadvary, B. (1992) J. Biol. Chem. 266, 20085-20091.
16. Lamzin, V. S., and Wilson, K. S. (1993) Acta Crystallogr. D49, 127-149.
17. Callas, D., Bacher, P., Iqbal, O., Hoppensteadt, D., and Fareed, J. (1994) Thromb. Res. 74, 193-205.
18. Callas, D. D., and Fareed, J. (1995) Thromb. Res. 78, 457-460.
19. Tapparelli, C., Metternich, R., Gfeller, P., Gafner, B., and Powling, M. (1995) Thromb. Haemostasis 73, 641-647.
20. Bone, R., Frank, D., Kettner, C. A., and Agard, D. A. (1989) Biochemistry 28, 7600-7609.
21. Katz, B. A., Finer-Moore, J., Mortezaei. R., Rich, D. H., and Stroud, R. M. (1995) Biochemistry 34, 8264-8280.
22. Weber, P. C., Lee, S.-L., Lewandowski, F. A., Scadt, M. C., Chang, C-H., and Kettner, C. A. (1995) Biochemistry 34, 3750-3757.
23. Rehse, P. H., Steinmetzer, T., Li, Y., Konishi, Y., and Cygler, M. (1995) Biochemistry 34, 11537-11544.
24. Zdanov, A., Wu, S., DiMaio, J., Konishi, Y., Li, Y., Wu, X., Edwards, B. F. P., Martin, P. D., and Cygler, M. (1993) Proteins: Struct., Funct., Genet. 17, 252-265.
25. Krishnan, R., Tulinsky, A., Vlasuk, G. P., Pearson, D., Vallar, P., Bergum, P., Brunck, T. K., and Ripka, W. C. (1996) Protein Sci. 5, 422-433.
26. Féthière, J., Tsuda, Y., Coulombe, R., Konishi, Y., and Cygler, M. (1996) Protein Sci. 5, 1174-1183.
27. Bode, W., Mayr, I., Baumann, U., Huber, R., Stone, S. R., and Hofsteenge, J. (1989) EMBO J. 8, 3467-3475.
28. Martin, P. D., Robertson, W., Turk, D., Huber, R., Bode, W., and Edwards, B. F. P. (1992) J. Biol. Chem. 267, 7911-7920.
29. Betz, A., Hofsteenge, J., and Stone, S. R. (1991) Biochemistry 30, 9848-9853.
30. Wang, J., Szewczuk, Z., Yue, S.-Y., Tsuda, Y., Konishi, Y., and Purisima, E. O. (1995) J. Mol. Biol. 253, 473-492.
31. Qiu, X., Padmanabhan, K. P., Carperos, V. E., Tulinsky, A., Kline, T., Maraganore, J. M., and Fenton, J. W., II (1992) Biochemistry 31, 11689-11698.
32. Rydel, T. J., Tulinsky, A., and Bode, W. (1991) J. Mol. Biol. 221, 583-601.
33. Tsuda, Y., Szewczuk, Z., Wang, J., Yue, S. Y., Purisima, E., and Konishi, Y. (1995) Biochemistry 34, 8708-8714.
34. Bachovchin, W. W., Wong, W. Y. L., Farr-Jones, S., Shenvi, A. B., and Kettner, C. A. (1988) Biochemistry 27, 7689-7697.
35. Tsilikounas, E., Kettner, C. A., and Bachovchin, W. W. (1992) Biochemistry 31, 12839-12846.
36. Perona, J. J., Craik, C. S., and Fletterick, R. J. (1993) Science 261, 620-621.
37. Claeson, G., Phillip, M., Agner, E., Scully, M. F., Metternich, R., Kakkar, V. V., DeSoyza, T., and Niu, L.-H. (1993) Biochem. J. 290, 309-312.
38. Tapparelli, C., Metternich, R., Erhardt, C., Zurini, M., Claeson, G., Scully, M. F., and Stone, S. R. (1993) J. Biol. Chem. 268, 4734-4741.
39. Elgendy, S., Claeson, G., Kakkar, V. V., Green, D., Patel, G., Goodwin, C. A., Baban, J. A., Scully, M. F., and Deadman, J. (1994) Tetrahedron 50, 3803-3812.
40. Hajduk, P. J., Meadows, R. P., and Fesik, S. W. (1997) Science 278, 497-499.
41. Tsilikounas, E., Kettner, C. A., and Bachovchin, W. W. (1993) Biochemistry 32, 12651-12655.
42. Phillip, M., Niua, L.-H., DeSoyza, T., Claeson, G., and Metternich, R. (1993) in The Design Of Synthetic Inhibitors of Thrombin (Claeson, G., et al, Eds.) pp 67-68, Plenum Press, New York and London.