Rational design of α-keto triglyceride analogues as inhibitors for Staphylococcus hyicus lipase

Biochemistry

Volumn 38, Issue 19, 1999, Pages 6346-6351

  Simons, Jan Willem F A ^b   Cox, Ruud C ^b   Egmond, Maarten R ^a   Verheij, Hubertus M ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBAMOYL PHOSPHATE; ETHER; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMICAL STRUCTURE; COMPETITIVE INHIBITION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MODIFICATION; ENZYME SUBSTRATE; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN INTERACTION; PROTEIN LOCALIZATION; STAPHYLOCOCCUS HYICUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

DRUG DESIGN; LIPASE; STAPHYLOCOCCUS; TRIGLYCERIDES;

BACTERIA (MICROORGANISMS); POSIBACTERIA; STAPHYLOCOCCUS HYICUS;

EID: 0033545839     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi982498b     Document Type: Article

References (39)

1. Jaeger, K.-E., Ransac, S., Dijkstra, B. W., Colson, C., van den Heuvel, M., and Misset, O. (1994) FEMS Microbiol. Lett. 15, 29-63.
2. Zaks, A., and Klibanov, A. M. (1984) Science 224, 1249-1251.
3. Mustranta, A., Forssell, P., and Poutanen, K. (1993) Enzyme Microb. Technol. 15, 133-139.
4. Winkler, F. K., D'Arcy, A., and Hunziker, W. (1990) Nature 343, 771-774.
5. van Tilbeurgh, H., Egloff, M.-P., Martinez, C., Rugani, N., Verger, R., and Cambillau, C. (1993) Nature 362, 814-820.
6. Brzozowski, A. M., Derewenda, U., Derewenda, Z. S., Dodson, G. G., Lawson, D. M., Turkenburg, J. P., Bjorkling, F., Huge-Jensen, B., Patkar, S. A., and Thim, L. (1991) Nature 351, 491-494.
7. Grochulski, P., Li, Y., Schrag, J., Bouthillier, F., Smith, P., Harrison, D., Rubin, B., and Cygler, M. (1993) J. Biol. Chem 268, 12843-12847.
8. Hermoso, J., Pignol, D., Kerfelec, B., Crenon, I., Chapus, C., and Fontecilla-Camps, J. C. (1996) J. Biol. Chem. 271, 18007-18016.
9. Kim, K. K., Song, H. K., Shin, D. H., Hwang, K. Y., and Suh, S. W. (1997) Structure 5, 173-185.
10. Schrag, J. D., Li, Y., Cygler, M., Lang, D., Burgdorf, T., Hecht, H.-J., Scmid, R., Schomburg, D., Rydel, T. J., Oliver, J. D., Strickland, L. C., Dunaway, C. M., Larson, S. B., Day, J., and McPherson, A. (1997) Structure 5, 187-202.
11. Grochulski, P., Bouthillier, F., Kazlauskas, R. J., Serreqi, A. N., Schrag, J. D., Ziomek, E., and Cygler, M. (1994) Biochemistry 33, 3494-3500.
12. Cygler, M., Grochulski, P., Kazlauskas, R. J., Schrag, J. D., Bouthellier, F., Rubin, B., Serregi, A. N., and Gupta, A. K. (1994) J. Am. Chem. Soc. 116, 3180-3186.
13. Egloff, M.-P., Marguet, F., Buono, G., Verger, R., Cambillau, C., and van Tilbeurgh, H. (1995) Biochemistry 34, 2751-2762.
14. Mannesse, M. L. M., Boots, J.-W. P., Dijkman, R., Slotboom, A. J., van der Hijden, H. T. W. M., Egmond, M. R., Verheij, H. M., and de Haas, G. H. (1995) Bichim. Biophys. Acta 1259, 56-64.
15. Stadler, P., Zandonella, G., Haalck, L., Spener, F., Hermetter, A., and Paltauf, F. (1996) Biochim. Biophys. Acta 1304, 229-244.
16. Aldridge, W. N., and Reiner, E. (1972) Enzyme Inhibitors as Substrates: Interactions of Esterases with Esters of Organophosphorus and Carbamic Acids, North-Holland, Amsterdam.
17. Bencsura, A., Enyedy, I., and Kovach, I. M. (1995) Biochemistry 34, 8989-8999.
18. Lang, D. A., Mannesse, M. L. M., de Haas, G. H., Verheij, H. M., and Dijkstra, B. W. (1998) Eur. J. Biochem. 254, 333-340.
19. Mehdi, S., Angelastro, M. R., Burkhart, J. P., Koehl, J. R., Peet, N. P., and Bey, P. (1990) Biochem. Biophys. Res. Commun. 166, 595-600.
20. Peet, N. P., Burkhart, J. P., Angelastro, M. R., Giroux, E. L., Mehdi, S., Bey, P., Kolb, M., Neises, B., and Schirlin, D. (1990) J. Med. Chem. 33, 394-407.
21. Conde-Frieboes, K., Reynolds, L. J., Lio, Y.-C., Hale, M. R., Wasserman, H. H., and Dennis, E. A. (1996) J. Am. Chem. Soc. 118, 5519-5525.
22. Simons, J.-W. F. A., Adams, H., Cox, R., Dekker, N., Götz, F., Slotboom, A. J., and Verheij, H. M. (1996) Eur. J. Biochem. 242, 760-769.
23. Hall, R. T., and Shaefer, W. E. (1954) Organic Analysis 2, 19-70.
24. De Haas, G. H., Dijkman, R., Ransac, S., and Verger, R. (1990) Biochim. Biophys. Acta 1046, 249-257.
25. Van Oort, M. G., Deveer, A. M. Th. J., Dijkman, R., Leuveling Tjeenk, M., Verheij, H. M., De Haas, G. H., Wenzig, E., and Götz, F. (1989) Biochemistry 28, 9278-9285.
26. Brodeck, U., Schweikert, K., Gentinetta, R., and Rottenberg, M. (1979) Biochim. Biophys. Acta 567, 357-369.
27. Gelb, M. H., Svaren, J. P., and Abeles, R. H. (1985) Biochemistry 24, 1813-1817.
28. Prestwich, G. D., Eng, W.-S., Roe, R. M., and Hammock, B. D. (1984) Arch. Biochem. Biophys. 228, 639-645.
29. Imperiali, B., and Abeles, R. H. (1986) Biochemistry 25, 3760-3767.
30. Street, I. P., Lin, H.-K., Laliberté, F., Ghomashchi, F., Wang, Z., Perrier, H., Tremblay, N. M., Huang, Z., Weech, P. K., and Gelb, M. H. (1993) Biochemistry 32, 5935-5940.
31. Brady, K., Wei, A., Ringe, D., and Abeles, R. H. (1990) Biochemistry 29, 7600-7607.
32. Takahashi, L. H., Radhakrisnan, R., Rosenfield, R. E., Jr., Meyer, E. F., Jr., Trainor, D. A., and Stein, M. (1988) J. Mol. Biol. 201, 423-428.
33. Liang, T.-C., and Abeles, R. H. (1987) Biochemistry 26, 7603-7608.
34. Trimble, L. A., Street, I. P., Perrier, H., Tremblay, N. M., Weech, P. K., and Bernstein, M. A. (1993) Biochemistry 32, 12560-12565.
35. Morrison, J. F. (1982) Trends Biochem. Sci. 7, 102-105.
36. Williams, J. W., and Morrison, J. F. (1979) Methods Enzvmol. 63, 437-467.
37. Stein, R. L., Strimpler, A. M., Edwards, P. D., Lewis, J. J., Mauger, R. C., Schwartz, J. A., Stein, M. M., Trainor, D. A., Wildonger, R. A., and Zottola, M. A. (1987) Biochemistry 26, 2682-2689.
38. Brady, K., and Abeles, R. (1990) Biochemistry 29, 7608-7617.
39. Stadler, P., Kovac, A., Haalck, L., Spener, F., and Paltauf, F. (1995) Eur. J. Biochem. 227, 335-343.