Selective modification of Trp19 in β-lactoglobulin by a new diazo fluorescence probe

Journal of Proteome Research

Volumn 6, Issue 9, 2007, Pages 3835-3841

  Bao, Zhijuan ^a   Wang, Shujuan ^a   Shi, Wen ^a   Dong, Suying ^a   Ma, Huimin ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

lactoglobulin; Analytical methods; Fluorescent probe; Metallocarbene; Selective tryptophan modification

Indexed keywords

1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 DIAZO 1,6 HEPTADIENE 3,5 DIONE; 8 ANILINO 1 NAPHTHALENESULFONIC ACID; ALKADIENE; BETA LACTOGLOBULIN; CARBENOID; CURCUMIN; RETINOL; RHODIUM; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; FLAME PHOTOMETRY; FLUORESCENCE ANALYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR PROBE; PH MEASUREMENT; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DOMAIN; PROTEIN MODIFICATION; PROTEIN STABILITY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; ULTRAVIOLET RADIATION;

ANILINO NAPHTHALENESULFONATES; ANIMALS; CARBON; CATTLE; CIRCULAR DICHROISM; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; LACTOGLOBULINS; LIGANDS; MODELS, CHEMICAL; PROTEOMICS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; TEMPERATURE; TRYPTOPHAN; VITAMIN A;

EID: 34948869850     PISSN: 15353893     EISSN: None     Source Type: Journal    
DOI: 10.1021/pr070284n     Document Type: Article

References (50)

1. D'Alfonso, L.; Collini, M.; Baldini, G. Biochemistry 2002, 41, 326-333.
2. Dong, S. Y.; Zhao, Z. W.; Ma, H. M. J. Proteome Res. 2006, 5, 26-31.
3. Cho, Y.; Batt, C. A.; Sawyer, L. J. Biol. Chem. 1994, 269, 11102-11107.
4. Friedman, M.; Cuq, J.-L. J. Agric. Food Chem. 1988, 36, 1079-1093.
5. Bao, Z. J.; Sun, S. N.; Chen, X. Q.; Li, J.; Dong, S. Y.; Ma, H. M. Angew. Chem., Int. Ed. 2006, 45, 6723-6725.
6. Weert, M. V.; Lagerwerf, F. M.; Haverkamp, J.; Heerma, W. J. Mass Spectrom. 1998, 33, 884-891.
7. Sapira, J. D.; Somani, S.; Shapiro, A. P.; Scheib, E. T.; Reihl, W. Metabolism 1971, 20, 474-486.
8. Vallejo-Manzur, F.; Mireles-Cabodevila, E.; Varon J. Am. J. Emerg. Med. 2005, 234, 521-524.
9. Murray, M. F. Lancet Infect. Dis. 2003, 3, 644-652.
10. Taylor, S. W.; Fahy, E.; Murray, J.; Capaldi, R. A.; Ghosh, S. S. J. Biol. Chem. 2003, 278, 19587-49590.
11. Aderson, L. B.; Maderia, M.; Ouellette, A. J.; Putnam-Evans, C.; Higgins, L.; Krick, T.; MacCoss, M. J.; Lim, H.; Yates, J. R., III; Barry, B. A. Proc. Natl. Acad. Sci. U.S.A 2002, 99, 14676-14681.
12. Dibowski, H.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 476-478.
13. Dong, S. Y.; Ma, H. M.; Chen, X. J.; Li, J. J. Proteome Res. 2005, 4, 161-166.
14. Duan, X. J.; Zhao, Z.; Ye, J. P.; Ma, H. M.; Xia, A. D.; Yang, G. Q.; Wang, C. C. Angew. Chem., Int. Ed. 2004, 43, 4216-4219.
15. Lundblad, R. L. Chemical Reagents for Protein Modification, 3rd ed.; CRC Press: Boca Raton, FL, 2005; pp 247-267.
16. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K. L. J. Am. Chem. Soc. 1990, 112, 1906-1912.
17. Gibe, R.; Kerr, M. A. J. Org. Chem. 2002, 67, 6247-6249.
18. Antos, J. M.; Francis, M. B. Curr. Opin. Chem. Biol. 2006, 10, 253-262.
19. Antos, J. M.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 10256-10257.
20. Moore, J.; Mcdermott, L.; Price, N. C.; Kelly, S. M.; Cooper, A.; Kennedy, M. W. Biochem. J. 1999, 340, 337-343.
21. Kunwar, A.; Barik A.; Pandey, R.; Priyadarsini, K. I. Biochim. Biophys. Acta 2006, 1760, 1513-1520.
22. Barik, A.; Priyadarsini, K. I.; Mohan, H. Photochem. Photobiol. 2003, 77, 597-603.
23. Valeur, B. Molecular Fluorescence Principle and Applications; Wiley-VCH: Weinheim, Germany, 2002; pp 62-63.
24. Khmelnitsky, Y. L.; Mozhaev, V. V.; Belova, A. B.; Sergeeva, M. V.; Martinek, K. Eur. J. Biochem. 1991, 198, 31-41.
25. Herskovits, T. T.; Jaillet, H. Science 1969, 163, 282-285.
26. Husband, F. A.; Garrood, M. J.; Mackie, A. R.; Burnett, G. R.; Wilde, P. J. J. Agric. Food Chem. 2001, 49, 859-866.
27. Reshetnyak, Y. K.; Burstein, E. A. Biophys. J. 2001, 81, 1710-1734.
28. Kumar, V.; Sharma, V. K.; Kalonia, D. S. Int. J. Pharm. 2005, 294, 193-199.
29. Dufour, E.; Hoa, G. H. B.; Haertlé, T. Biochim. Biophys. Acta 1994, 1206, 166-172.
30. Dufour, E.; Genot, C.; Haertlé, T. Biochim. Biophys. Acta 1994, 1205, 105-112.
31. Croguennec, T.; Molle, D.; Mehra, R.; Bouhallab, S. Protein Sci. 2004, 13, 1340-1346.
32. Bhattacharjee, C.; Das, K. P. Eur. J. Biochem. 2000, 267, 3957-3964.
33. Fessas, D.; Lametti, S.; Schiraldi, A.; Bonomi, F. Eur. J. Biochem. 2001, 268, 5439-5448.
34. Wang, F.; Huang, W. J. Pharm. Biomed. Anal. 2007, 43, 393-398.
35. Song, C. Y.; Chen, W. L.; Yang, M. C.; Huang, J. P.; Mao, S. J. T. J. Biol. Chem. 2005, 280, 3574-3582.
36. Ragona, L.; Fogolari, F.; Catalano, M.; Ugolini, R.; Zetta, L. J. Biol. Chem. 2003, 278, 38840-38846.
37. Sakurai, K.; Goto, Y. J. Mol. Biol. 2006, 356, 483-496.
38. Adams, J. J.; Anderson, B. F.; Norris, G. E.; Creamer, L. K.; Jameson, G. B. J. Struct. Biol. 2006, 154, 246-254.
39. Yagi, M.; Sakurai, K.; Kalidas, C.; Batt, C. A.; Goto, Y. J. Biol. Chem. 2003, 278, 47009-47015.
40. Iametti, S.; Scaglioni, L.; Mazzini, S.; Vecchio, G.; Bonomi, F. J. Agric. Food Chem. 1998, 46, 2159-2166, and references therein.
41. Kauffmann, E.; Darnton, N. C.; Austin, R. H.; Batt, C.; Gerwert, K. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 6646-6649.
42. Yang, J.; Dunker, A. K.; Powers, J. R.; Clark, S.; Swanson, B. G. J. Agric. Food Chem. 2001, 49, 3236-3243.
43. Viseu, M. I.; Carvalho, T. I.; Costa, S. M. B. Biophys. J. 2004, 86, 2392-2402.
44. Creamer, L. K. Biochemistry 1995, 34, 7170-7176.
45. Wang, Q.; Allen, J. C.; Swaisgood, H. E. J. Dairy Sci. 1997, 80, 1047-1053.
46. Andrade, S. M.; Carvalho, T. I.; Viseu, M. I.; Costa, S. M. B. Eur. J. Biochem. 2004, 271, 734-744.
47. Kanjilal, S.; Taulier, N.; Huérou, J. -Y. L.; Gindre, M.; Urbach, W.; Waks, M. Biophys. J. 2003, 85, 3928-3934.
48. Futterman, S.; Heller, J. J. Biol. Chem. 1972, 247, 5168-5172.
49. Katakura, Y.; Totsuka, M.; Ametani, A.; Kaminogawa, S. Biochim. Biophys. Acta 1994, 1207, 58-67.
50. Papiz, M. Z.; Sawyer, L.; Eliopoulos, E. E.; North, A. C. T.; Findlay, J. B. C.; Sivaprasadarao, R.; Jones, T. A.; Newcomer, M. E.; Kraulis, P. J. Nature 1986, 324, 383-385.