Synthesis of 3,5-difluorotyrosine-containing peptides: Application in substrate profiling of protein tyrosine phosphatases

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4605-4608

  Gopishetty, Bhaskar ^a   Ren, Lige ^a   Waller, Tiffany M ^a   Wavreille, Anne Sophie ^a   Lopez, Miguel ^a   Thakkar, Amit ^a   Zhu, Jinge ^a   Pei, Dehua ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIFLUOROTYROSINE; 3,5-DIFLUOROTYROSINE; DRUG DERIVATIVE; PEPTIDE; PROTEIN TYROSINE PHOSPHATASE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; MASS SPECTROMETRY; METABOLISM; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN TYROSINE PHOSPHATASES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SUBSTRATE SPECIFICITY; TYROSINE;

EID: 58149170357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801868a     Document Type: Article

References (22)

1. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-1369.
2. Battaini, G.; Monzani, E.; Casella, L.; Lonardi, E.; Tepper, A. W. J. W.; Canters, G. W.; Bubacco, L. J. Biol. Chem. 2002, 277, 44606-44612.
3. Phillips, R. S.; Von Tersch, R. L.; Secundo, F. Eur. J. Biochem. 1997, 244, 658-663.
4. Kim, K.; Cole, P. A. J. Am. Chem. Soc. 1998, 120, 6851-6858.
5. Martin, B.; Pallen, C. J.; Wang, J. H.; Graves, D. J. J. Biol. Chem. 1985, 260, 14932-14937.
6. Brooks, B.; Philips, R. S.; Benisek, W. F. Biochemistry 1998, 37, 9738-9742.
7. Yee, C. S.; Chang, M. C. Y.; Ge, J.; Nocera, D. G.; Stubbe, J. J. Am. Chem. Soc. 2003, 125, 10506-10507.
8. Garaud, M.; Pei, D. J. Am. Chem. Soc. 2007, 129, 5366-5367.
9. Seyedsayamdost, M. R.; Reece, S. Y.; Nocera, D. G.; Stubbe, J. J. Am. Chem. Soc. 2006, 128, 1569-1579.
10. Kirk, K. L. J. Org. Chem. 1980, 45, 2015-2016.
11. Yamamoto, T.; Ikawa, S.; Akiyama, T.; Nomura, N.; Miyajima, N.; Saito, T.; Toyoshima, K. Nature 1986, 319, 230-234.
12. (a) Zhang, Z.-Y.; Thieme-Sefler, A. M.; Maclean, D.; McNamara, D. J.; Dobrusin, E. M.; Sawyer, T. M.; Dixon, J. E. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4446-4450.
13. (b) Zhang, Z.-Y.; Maclean, D.; McNamara, D. J.; Sawyer, T. K.; Dixon, J. E. Biochemistry 1994, 33, 2285-2290.
14. Meldal, M. Tetrahedron Lett. 1992, 33, 3077-3080.
15. (a) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
16. (b) Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86.
17. (c) Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487-493.
18. Winder, A. J.; Harris, H. Eur. J. Biochem. 1991, 198, 317-326.
19. Thakkar, A.; Wavreille, A.-S.; Pei, D. Anal. Chem. 2006, 78, 5935-5939.
20. (a) Pellegriini, M. C.; Liang, H.; Mandiyan, S.; Wang, K.; Yuryev, A.; Vlattas, I.; Sytwu, T.; Li, Y.-C.; Wennogle, L. P. Biochemistry 1998, 37, 15598-15606.
21. (b) Vetter, S. W.; Keng, Y.-F.; Lawrence, D. S.; Zhang, Z.-Y. J. Biol. Chem. 2000, 275, 2265-2268.
22. (c) Walchli, S.; Espanel, X.; Harrenga, A.; Rossi, M.; Cesareni, G.; van Huijsduiinen, R. H. J. Biol. Chem. 2004, 279, 311-318.