Design of amino acid aldehydes as transition-state analogue inhibitors of arginase

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10278-10284

  Shin, Hyunshun ^a   Cama, Evis ^a   Christianson, David W ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CHEMICAL BONDS; ENZYME INHIBITION; HYDROLYSIS; MANGANESE COMPOUNDS;

ELECTROPHILIC ALDEHYDE; HYDROXIDE ION; METALLOENZYME;

AMINO ACIDS;

ALDEHYDE; AMINO ACID; ARGINASE; ENZYME INHIBITOR; METALLOPROTEIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; KINETICS; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ALDEHYDES; AMINO ACIDS; ARGINASE; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HEPTANOIC ACIDS; KINETICS; MODELS, MOLECULAR;

EID: 4143103583     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047788w     Document Type: Article

References (40)

1. Christianson, D. W.; Cox, J. D. Annu. Rev. Biochem. 1999, 68, 33-57.
2. Ash, D. E.; Cox, J. D.; Christianson, D. W. Metal Ions in Biological Systems; Sigel, A., Sigel, H., Eds.; M. Dekker: New York, 2000; Vol. 37 (Manganese and its Role in Biological Processes), pp 408-428.
3. Morris, S. M., Jr. Annu. Rev. Nutr. 2002, 22, 87-105.
4. Kanyo, Z. F.; Scolnick, L. R.; Ash, D. E.; Christianson, D. W. Nature 1996, 383, 554-557.
5. Cama, E.; Colleluori, D. M.; Emig, F. A.; Shin, H.; Kim, S. W.; Kim, N. N.; Traish, A. M.; Ash, D. E.; Christianson, D. W. Biochemistry 2003, 42, 8445-8451.
6. Bewley, M. C.; Jeffrey, P. D.; Patchett, M. L.; Kanyo, Z. F.; Baker, E. N. Structure 1999, 7, 435-448.
7. Kuhn, N. J.; Talbot, J.; Ward, S. Arch. Biochem. Biophys. 1991, 286, 217-221.
8. Cama, E.; Emig, F. A.; Ash, D. E.; Christianson, D. W. Biochemistry 2003, 42, 7748-7758.
9. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334-338.
10. Cama, E.; Shin, H. S.; Christianson, D. W. J. Am. Chem. Soc. 2003, 125, 13052-13057.
11. Baggio, R.; Elbaum, D.; Kanyo, Z. F.; Carroll, P. J.; Cavalli, R. C.; Ash, D. E.; Christianson, D. W. J. Am. Chem. Soc. 1997, 119, 8107-8108.
12. Kim, N. N.; Cox, J. D.; Baggio, R. F.; Emig, F. A.; Mistry, S.; Harper, S. L.; Speicher, D. W.; Morris, S. M., Jr.; Ash, D. E.; Traish, A. M.; Christianson, D. W. Biochemistry 2001, 40, 2678-2688.
13. Cox, J. D.; Kim, N. N.; Traish, A. M.; Christianson, D. W. Nat. Struct. Biol. 1999, 6, 1043-1047.
14. Christianson, D. W.; Lipscomb, W. N. Acc. Chem. Res. 1989, 22, 62-69.
15. Pauling, L. Chem. Eng. News 1946, 24, 1375-1377.
16. Andersson, L.; Isley, T. C.; Wolfenden, R. Biochemistry 1982, 21, 4177-4180.
17. Andersson, L.; MacNeela, J.; Wolfenden, R. Biochemistry 1985, 24, 330-333.
18. Galardy, R. E.; Kortylewicz, Z. P. Biochemistry 1984, 23, 2083-2087.
19. Christianson, D. W.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 6840-6844.
20. Sträter, N.; Lipscomb, W. N. Biochemistry 1995, 34, 14792-14800.
21. Rüegg, U. T.; Russell, A. S. Anal. Biochem. 1980, 102, 206-212.
22. Cama, E.; Pethe, S.; Boucher, I.-L.; Han, S., Emig, F. A.; Ash, D. E.; Viola, R. E.; Mansuy, D.; Christianson, D. W. Biochemistry 2004, 43, 8987-8999.
23. Kanyo, Z. F.; Chen, C.-Y.; Daghigh, F.; Ash, D. E.; Christianson, D. W. J. Mol. Biol. 1992, 224, 1175-1177.
24. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
25. Navaza, J. Acta Crystallogr. 1994, A50, 157-163.
26. Collaborative Computational Project, No. 4. Acta Crystallogr. 1994, D50, 760-763.
27. Jones, T. A.; Zou, J.-Y.; Cowan, S. W.; Kjeldgaard, M. Acta Crystallogr. 1991, A47, 110-119.
28. Brünger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J.-S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr. 1998, D54, 905-921.
29. Esnouf, R. M. J. Mol. Graphics 1997, 15, 132-134.
30. Merritt, E. A.; Bacon, D. J. Methods Enzymol. 1997, 277, 505-524.
31. Adamczyk, M.; Johnson, D. D.; Reddy, R. E. Tetrahedron: Asymmetry 1999, 10, 775-781.
32. Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741-3744.
33. Padrón, J. M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W. A.; Martín, V. S. Tetrahedron: Asymmetry 1998, 9, 3381-3394.
34. Martín, R.; Islas, G.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 2001, 57, 6367-6374.
35. Samano, V.; Robins, M. J. J. Org. Chem. 1990, 55, 5186-5188.
36. Ellison, R. A.; Lukenbach, E. R.; Chiu, C. Tetrahedron Lett. 1975, 15, 499-502.
37. Lewis, C. A.; Wolfenden, R. Biochemistry 1977, 16, 4886-4890.
38. Pocker, Y.; Sarkanen, S. Adv. Enzymol. 1978, 47, 149-274.
39. Custot, J.; Boucher, J.-L.; Vadon, S.; Guedes, C.; Dijols, S.; Delaforge, M.; Mansuy, D. J. Biol. Inorg. Chem. 1996, 1, 73-82.
40. Collet, S.; Carreaux, F.; Boucher, J.-L.; Pethe, S.; Lepoivre, M.; Danion-Bougot, R.; Danion, D. J. Chem. Soc., Perkin Trans. 2000, 1, 177-182.