Inactivation of microbial arginine deiminases by L-canavanine

Journal of the American Chemical Society

Volumn 130, Issue 6, 2008, Pages 1918-1931

  Li, Ling ^a   Li, Zhimin ^a   Chen, Danqi ^a   Lu, Xuefeng ^a   Feng, Xiaohua ^a   Wright, Elizabeth C ^a   Solberg, Nathan O ^a   Dunaway Mariano, Debra ^a   Mariano, Patrick S ^a   Galkin, Andrey ^b   Kulakova, Liudmila ^b   Herzberg, Osnat ^b   Green Church, Kari B ^c   Zhang, Liwen ^c  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE   (United States)

^c OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DEIMINASE (ADI); HYDROLYTIC CONVERSION;

AMMONIA; CATALYSIS; DEGRADATION; ENZYME INHIBITION; HYDROLYSIS; MASS SPECTROMETRY;

ENZYME KINETICS;

ALKYL GROUP; AMMONIA; ARGININE; ARGININE DEIMINASE; CANAVANINE; CITRULLINE; HOMOSERINE; ION; O UREIDOHOMOSERINE; THIOCARBAMIC ACID DERIVATIVE; THIOL DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACILLUS CEREUS; BURKHOLDERIA MALLEI; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INACTIVATION; ENZYME SUBSTRATE COMPLEX; ESCHERICHIA COLI; GIARDIA LAMBLIA; HYDROLYSIS; KINETICS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; PSEUDOMONAS AERUGINOSA; REACTION ANALYSIS; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; X RAY CRYSTALLOGRAPHY;

ANIMALS; BACILLUS CEREUS; BURKHOLDERIA MALLEI; CANAVANINE; CATALYSIS; ENZYME ACTIVATION; ENZYME INHIBITORS; ESCHERICHIA COLI; GIARDIA LAMBLIA; HYDROLASES; HYDROLYSIS; KINETICS; MOLECULAR CONFORMATION; PSEUDOMONAS AERUGINOSA; STEREOISOMERISM;

EID: 39049108427     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0760877     Document Type: Article

References (50)

1. Abdelal, A. T. Annu. Rev. Microbiol. 1979, 33, 139-168.
2. Cunin, R.; Glansdorff, N.; Pierard, A.; Stalon, V. Microbiol. Rev. 1986, 50, 314-352.
3. Zuniga, M.; Perez, G.; Gonzalez-Candelas, F. Mol. Phylogenet. Evol. 2002, 25, 429-444.
4. (a) Dong, Y.; Chen, Y. Y.; Snyder, J. A.; Burne, R. A. Appl. Environ. Microbiol. 2002, 68, 5549-5553.
5. (b) Knodler, L. A.; Sekyere, E. O.; Stewart, T. S.; Schofield, P. J.; Edwards, M. R. J. Biol. Chem. 1998, 273, 4470-4477.
6. Baur, H.; Luethi, E.; Stalon, V.; Mercenier, A.; Haas, D. Eur. J. Biochem. 1989, 179, 53-60.
7. Shibatani, T.; Kakimoto, T.; Chibata, I. J. Biol. Chem. 1975, 250, 4580-4583.
8. Kondo, K.; Sone, H.; Yoshida, H.; Toida, T.; Kanatani, K.; Hong, Y. M.; Nishino, N.; Tanaka, J. I. Mol. Gen. Genet. 1990, 221, 81-86.
9. Weickmann, J. L.; Fahrney, D. E. J. Biol. Chem. 1977, 252, 2615-2620.
10. Schimke, R. T.; Berlin, C. M.; Sweeney, E. W.; Carroll, W. R. J. Biol. Chem. 1966, 241, 2228-2236.
11. Schofield, P. J.; Edwards, M. R.; Matthews, J.; Wilson, J. R. Mol. Biochem. Parasitol. 1992, 51, 29-36.
12. Linstead, D.; Cranshaw, M. A. Mol. Biochem. Parasitol. 1983, 8, 241-252.
13. Yarlett, N.; Lindmark, D. G.; Goldberg, B.; Moharrami, M. A.; Bacchi, C. J. J. Eukaryotic Microbiol. 1994, 41, 554-559.
14. Biagini, G. A.; Yarlett, N.; Ball, G. E.; Billetz, A. C.; Lindmark, D. G.; Martinez, M. P.; Lloyd, D.; Edwards, M. R. Mol. Biochem. Parasitol. 2003, 128, 11-19.
15. Silva, L. M.; Baums, C. G.; Rehm, T.; Wisselink; H. J.; Goethe, R.; Valentin- Weigand, P. Vet Microbiol 2006 115, 117-27.
16. Gruening, P.; Fulde, M.; Valentin-Weigand, P.; Goethe, R. J. Bacteriol. 2006 188, 361-9.
17. Makhlin, J.; Kofman, T.; Borovok, I.; Kohler, C.; Engelmann, S.; Cohen, G.; Aharonowitz, Y. J. Bacteriol. 2007 189, 5976-86.
18. Seggewiss, J.; Becker, K.; Kotte, O.; Eisenacher, M.; Yazdi, M. R.; Fischer, A.; McNamara, P.; Al Laham, N.; Proctor, R.; Peters, G.; Heinemann, M.; von Eiff, C. J. Bacteriol. 2006, 188, 7765-77.
19. Galkin, A.; Kulakova, L.; Sarikaya, E.; Lim, K.; Howard, A.; Herzberg, O. J. Biol. Chem. 2004, 279, 14001-14008.
20. Galkin, A.; Lu, X. F.; Dunaway-Mariano, D.; Herzberg, O. J. Biol. Chem. 2005, 280, 34080-34087.
21. Lu, X. F.; Li, L.; Wu, R.; Mariano, P. S.; Dunaway-Mariano, D. Biochemistry 2006, 45, 1162-1172.
22. Lu, X.; Galkin, A.; Herzberg, O.; Dunaway-Mariano, D. J. Am. Chem. Soc. 2004, 126, 5374-5375.
23. Lu, X. F.; Li, L.; Feng, X. H.; Dunaway-Mariano, D.; Engen, D.; Mariano, P. S. J. Am. Chem. Soc. 2005, 127, 16412-16413.
24. Luo, Y.; Arita, K.; Bhatia, M.; Knuckley, B.; Lee, Y. H.; Stallcup, M. R.; Sato, M.; Thompson P. R. Biochemistry 2006, 45, 11727-36.
25. Luo, Y.; Knuckley, B.; Lee, Y. H.; Stallcup, M. R.; Thompson, P. R. J. Am. Chem. Soc. 2006, 128, 1092-3.
26. Stone, E. M.; Schaller, T. H.; Bianchi, H.; Person, M. D.; Fast, W. Biochemistry 2005, 44, 13744-52.
27. Hong, L; Fast, W, J. Biol. Chem. 2007, 282, 34684-34692.
28. Li, L.; Li, Z.; Wang, C. H.; Xu, D.; Mariano, P. S.; Dunaway-Mariano, D.; Guo, H. Biochemistry submitted for review.
29. Knodler, L. A.; Schofield, P. J.; Edwards, M. R. Microbiology 1995, 141, 2063-2070.
30. (a) Hudson, R. F. Angew. Chem., Int. Ed. 1973, 12, 36-56.
31. (b) Gerstein, J.; Jencks, W. P. J. Am. Chem. Soc. 1964, 86, 4655-4663.
32. (c) This effect is proposed to be responsible for cysteine protease inhibition by azapeptide analogs (ref 29d).
33. (d) Magrath, J.; Abeles, R. H. J. Med. Chem. 1992, 35, 4279-4283.
34. Kihara, H.; Snell, E. E. J. Biol. Chem. 1957, 226, 485-495.
35. Smith, D. W.; Ganaway, R. L.; Fahrney, D. E. J. Biol. Chem. 1978, 253, 6016-6020.
36. Rosenthal, G. A. Q. Rev. Biol. 1977, 52, 155-178.
37. Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145.
38. Silverman, R. Mechanism-based Enzymes Inactivators: Chemistry and Enzymology; Academic Press: Boca Raton, FL, 1988.
39. Raymackers, J.; Daniels, A.; De Brabandere, V.; Missiaen, C.; Dauwe, M.; Verhaert, P.; Vanmechelen, E.; Meheus, L. Electrophoresis 2000, 21, 2266-2283.
40. Gustafsson, E.; Thoren, K.; Larsson, T.; Davidsson, P.; Karlsson, K. A.; Nilsson, C. L. Rapid Commun. Mass Spectrom. 2001, 15, 428-432.
41. Biemann, K. Appendix 5. Nomenclature for peptide fragment ions (positive ions). Methods Enzymol. 1990, 193, 886-887.
42. Das, K.; Butler, G. H.; Kwiatkowski, V.; Clark, A. D., Jr.; Yadav, P.; Arnold, E. Structure 2004, 12, 657.
43. Albert, A.; Goldacre, R.; Phillips, J. J. Chem. Soc. 1948, 2240.
44. Tomiyama, T. I. J. Biol. Chem. 1935, 111, 45;
45. Boyar, A.; Marsh, R. E. J. Am. Chem. Soc. 1982, 104, 1995-1923.
46. Klayman, D. L.; Shine, R. J.; Bower, J. D. J. Org. Chem. 1972, 37, 1532-1537.
47. Chaturvedi, R. K.; MacMahon, A. E.; Schmir, G. L. J. Am. Chem. Soc. 1967, 89, 6984-6993.
48. Dufour, E.; Storer, A. C.; Menard, R. Biochemistry 1995, 34, 16382-16388.
49. Boehlein, S. K.; Rosa-Rodriguez, J. G.; Schuster, S. M.; Richards, N. G. J. Am. Chem. Soc. 1997, 119, 5785-5791.
50. http://pymol.sourceforge.net, DeLano Scientific LLC, San Carlos, California.