Phosphorylimidazole derivatives: Potentially biosignaling molecules

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8003-8008

  Orth, Elisa S ^a   Wanderlind, Eduardo H ^a   Medeiros, Michelle ^a   Oliveira, Pedro S M ^a   Vaz, Boniek G ^b   Eberlin, Marcos N ^b   Kirby, Anthony J ^c   Nome, Faruk ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED PHOSPHATES; ESI-MS/MS; HALF LIVES;

PHOSPHORYLATION;

RADIOACTIVITY;

IMIDAZOLE DERIVATIVE; ORGANOPHOSPHATE; PHOSPHORYLIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; HALF LIFE TIME; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; SIGNAL TRANSDUCTION;

DRUG DESIGN; ESTERS; IMIDAZOLES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; SIGNAL TRANSDUCTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 80054103919     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2017394     Document Type: Article

References (29)

1. Fersht, A. R. Structure and Mechanism in Protein Science; 2nd ed.; Freeman: New York, 1999.
2. Raines, R. T. Chem. Rev. 1998, 98, 1045.
3. Steeg, P. S.; Palmieri, D.; Ouatas, T.; Salerno, M. Cancer Lett. 2003, 190, 1.
4. Breslow, R.; Dong, S. D.; Webb, Y.; Xu, R. J. Am. Chem. Soc. 1996, 118, 6588.
5. Klumpp, S.; Krieglstein, J. Eur. J. Biochem. 2002, 269, 1067.
6. Attwood, P. V.; Piggott, M. J.; Zu, X. L.; Besant, P. G. Amino Acids 2007, 32, 145.
7. Besant, P. G.; Attwood, P. V. Biochim. Biophys. Acta, Proteins Proteomics 2005, 1754, 281.
8. Cohen, P. Eur. J. Biochem. 2001, 268, 5001.
9. Breslow, R. J. Biol. Chem. 2009, 284, 1337.
10. Breslow, R. Acc. Chem. Res. 1995, 28, 146.
11. Niittymaki, T.; Lonnberg, H. Org. Biomol. Chem. 2006, 4, 15.
12. Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 8931.
13. Thomas, J. M.; Yoon, J. K.; Perrin, D. M. J. Am. Chem. Soc. 2009, 131, 5648.
14. Hultquist, D. E.; Moyer, R. W.; Boyer, P. D. Biochemistry 1966, 5, 322.
15. Hultquist, D. E. Biochim. Biophys. Acta 1968, 153, 329.
16. Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1965, 87, 3199.
17. Lloyd, G. J.; Cooperman, B. S. J. Am. Chem. Soc. 1971, 93, 4883.
18. Orth, E. S.; Brandao, T. A. S.; Milagre, H. M. S.; Eberlin, M. N.; Nome, F. J. Am. Chem. Soc. 2008, 130, 2436.
19. Orth, E. S.; Brandao, T. A. S.; Souza, B. S.; Pliego, J. R.; Vaz, B. G.; Eberlin, M. N.; Kirby, A. J.; Nome, F. J. Am. Chem. Soc. 2010, 132, 8513.
20. Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 1165.
21. Bunton, C. A.; Farber, S. J. J. Org. Chem. 1969, 34, 767.
22. Orth, E. S.; da Silva, P. L. F.; Mello, R. S.; Bunton, C. A.; Milagre, H. M. S.; Eberlin, M. N.; Fiedler, H. D.; Nome, F. J. Org. Chem. 2009, 74, 5011.
23. Silversmith, R. E.; Appleby, J. L.; Bourret, R. B. Biochemistry 1997, 36, 14965.
24. Domingos, J. B.; Longhinotti, E.; Brandão, T. A. S.; Santos, L. S.; Eberlin, M. N.; Bunton, C. A.; Nome, F. J. Org. Chem. 2004, 69, 7898.
25. Kirby, A. J.; Manfredi, A. M.; Souza, B. S.; Medeiros, M.; Priebe, J. P.; Brandao, T. A. S.; Nome, F. Arkivoc 2009, 28.
26. Kirby, A. J.; Souza, B. S.; Medeiros, M.; Priebe, J. P.; Manfredi, A. M.; Nome, F. Chem. Commun. 2008, 4428.
27. McQuarrie, D. A.; Simon, J. D. Physical Chemistry: A Molecular Approach; University Science Books: Mill Valley, CA, 1997.
28. Rawji, G.; Milburn, R. M. J. Org. Chem. 1981, 46, 1205.
29. Martell, A. E.; Smith, R. M.; Motekaitis, R. J. NIST Critical Stability Constants of Metal Complexes Database: NIST Standard Reference Database 46; NIST: Gaithersburg, MD, 1993.