Facile incorporation of a phosphatase activity-dependent quinone methide generating motif into phosphotyrosine

Synthesis

Volumn , Issue 22, 2009, Pages 3765-3768

  Shen, Kui ^a   Qi, Lixin ^a   Ravula, Mohini ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Amino acids; Fluorine; Hydrolyses; Phosphates; Quinomethanes; Quinone methides

Indexed keywords

FUNCTIONAL GROUP TRANSFORMATIONS; PHENOL MOIETY; PHOSPHATASE ACTIVITY; PHOSPHOTYROSINE; QUINONE METHIDE;

FLUORINE; FUNCTIONAL GROUPS; HYDROLYSIS; ORGANIC ACIDS; PHENOLS; PHOSPHATASES; PHOSPHATES;

AMINO ACIDS;

FUNCTIONAL GROUP; METHYL N CBZ TYROSINATE; PHENOL; PHOSPHATASE; PHOSPHOTYROSINE; QUINONE DERIVATIVE; TYROSINE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL LABELING; ENZYME ACTIVITY; PROTEIN ANALYSIS; PROTEIN SYNTHESIS; SYNTHESIS;

EID: 73649147705     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217025     Document Type: Article

References (31)

1. (a) Hunter, T. Cell 2000, 100, 113.
2. (b) Julien, S. G.; Dube, N.; Read, M.; Penney, J.; Paquet, M.; Han, Y.; Kennedy, B. P.; Muller, W. J.; Tremblay, M. L. Nature Genetics 2007, 39, 338.
3. (c) Saha, S.; Bardelli, A.; Buckhaults, P.; Velculescu, V. E.; Rago, C.; St. Croix, B.; Romans, K. E.; Choti, M. A.; Lengauer, C.; Kinzler, K. W.; Vogelstein, B. Science 2001, 294, 1343.
4. (d) Zeng, Q.; Dong, J. M.; Guo, K.; Li, J.; Tan, H. X.; Koh, V.; Pallen, C. J.; Manser, E.; Hong, W. Cancer Res. 2003, 63, 2716.
5. (e) Alonso, A.; Sasin, J.; Bottini, N.; Friedberg, I.; Friedberg, I.; Osterman, A.; Godzik, A.; Hunter, T.; Dixon, J.; Mustelin, T. Cell 2004, 117, 699.
6. (a) Blanchetot, C.; Chagnon, M.; Dube, N.; Halle, M.; Tremblay, M. L. Methods 2005, 35, 44.
7. (b) Zhang, X.; Guo, A.; Yu, J.; Possemato, A.; Chen, Y.; Zheng, W.; Polakiewicz, R. D.; Kinzler, K. W.; Vogelstein, B.; Veleulescu, V. E.; Wang, Z. J. Proč. Natl. Acad. Sci. U.S.A. 2007, 104, 4060.
8. (a) Cravatt, B. F.; Wright, A. T.; Kozarich, J. W. Annu. Rev. Biochem. 2008, 77, 383.
9. (b) Luo, Y.; Knuckley, B.; Bhatia, M.; Thompson, P. R. J. Am. Chem. Soc. 2006, 128, 1092.
10. Shen, K.; Qi, L.; Ravula, M.; Klimaszewski, K. Bioorg. Med. Chem. Lett. 2009, 19, 3264.
11. (a) Myers, J. K.; Widlanski, T. S. Science 1993, 262, 1451.
12. (b) Wang, Q.; Dechert, U.; Jirik, F.; Withers, S. G. Biochem. Biophys. Res. Commun. 1994, 200, 577.
13. (c) Born, T. L.; Myers, J. K.; Widlanski, T. S.; Rusnak, F. J. Biol. Chem. 1995, 270, 25651.
14. (d) Bolton, J. L.; Turnipseed, S. B.; Thompson, J. A. Chem.-Biol. Interact. 1997, 107, 185.
15. (e) Betley, J. R.; Cesaro-Tadic, S.; Mekhalfia, A.; Rickard, J. H.; Denham, H.; Partridge, L. J.; Plückthun, A.; Blackburn, G. M. Angew. Chem. Int. Ed. 2002, 41, 775.
16. (f) Zhu, Q.; Huang, X.; Chen, G. Y. J.; Yao, S. Q. Tetrahedron Lett. 2003, 44, 2669.
17. (g) Lo, L.-C.; Chiang, Y.-L.; Kuo, C-H.; Liao, H.-K.; Chen, Y.-J.; Lin, J.-J. Biochem. Biophys. Res. Commun. 2004, 326, 30.
18. (a) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
19. (b) Smyth, M. S.; Burke, T. R. Jr. Org. Prep. Proced. Int. 1996, 28, 77.
20. (c) Hubbard, C. E.; Barrios, A. M. Bioorg. Med. Chem. Lett. 2008, 18, 679.
21. (a) Dhawan, B .; Redmore, D. J. Org. Chem. 1984, 49, 4018.
22. (b) Dhawan, B.; Redmore, D. J. Org. Chem. 1986, 51, 179.
23. (c) Tian, Z.; Gu, C; Roeske, R. W.; Zhou, M.; Van Ettan, R. L. Int. J. Pept. Protein Res. 1993, 42, 155.
24. (d) Wakamiya, T.; Nishida, T.; Togashi, R.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 465.
25. (a) Hansen, T. V.; Skattebøl, L. Org Synth. 2005, 82, 64.
26. (b) Hofsløkken, N. U.; Skattebøl, L. Acta Chem. Scand. 1999, 53, 258.
27. Rachele, J. R. J. Org. Chem. 1963, 28, 2898.
28. (a) Smyth, M. S.; Burke, T. R. Jr. Tetrahedron Lett. 1994, 35, 551.
29. (b) Schwarzer, D.; Zhang, Z.; Zheng, W.; Cole, P. A. J. Am. Chem. Soc. 2006, 128, 4192.
30. Pascal, R.; Sola, R. Tetrahedron Lett. 1998, 39, 5031.
31. Shen, K. Methods 2007, 42, 234.