Synthesis and Biological Activity of Photoactivatable N-Ras Peptides and Proteins

Journal of the American Chemical Society

Volumn 125, Issue 42, 2003, Pages 12749-12758

  Völkert, Martin ^a,b   Uwai, Koji ^a,b,c   Tebbe, Andreas ^a   Popkirova, Boriana ^a   Wagner, Melanie ^a   Kuhlmann, Jürgen ^a   Waldman, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

^c TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; PROTEINS; SYNTHESIS (CHEMICAL);

BIOLOGICAL ACTIVITY;

POLYPEPTIDES;

BENZOPHENONE; FUNCTIONAL GROUP; GUANINE NUCLEOTIDE EXCHANGE FACTOR; HEPTAPEPTIDE; MECYSTEINE; RAS PROTEIN;

ARTICLE; CHEMICAL BOND; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PHOTOACTIVATION; PHOTOAFFINITY LABELING; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERIZATION; PRENYLATION; PROTEIN PROTEIN INTERACTION; WESTERN BLOTTING;

ANIMALS; BENZOPHENONES; CYSTEINE; OLIGOPEPTIDES; PC12 CELLS; PEPTIDE FRAGMENTS; PHOTOCHEMISTRY; RAS PROTEINS; RATS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 10744228189     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036178d     Document Type: Article

References (35)

1. Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem., Int. Ed. 1998, 37, 688-749.
2. Wittinghofer, A.; Waldmann, H. Angew. Chem., Int. Ed. 2000, 39, 4192-4214.
3. Barbacid, M. Annu. Rev. Biochem. 1987, 56, 779-789.
4. Hanahan, D.; Weinberg, R. A. Cell 2000, 100, 57-70.
5. Hancock, J. F.; Paterson, H.; Marshall, C. J. Cell 1990, 63, 133-139.
6. Völkert, M.; Wagner, M.; Peters, C.; Waldmann, H. Biol. Chem. 2001, 382, 1133-1145.
7. Sinensky, M. Biochim. Biophys. Acta 2000, 1529, 203-209.
8. McGeady, P.; Porfiri, E.; Gelb, H. Bioorg. Med. Chem. Lett. 1997, 7, 145-150.
9. Porfiri, E.; Evans, T.; Chardin, P.; Hancock, J. F. J. Biol. Chem. 1994, 269, 22672-22677.
10. Kadereit, D.; Kuhlmann, J.; Waldmann, H. ChemBioChem 2000, 1, 144-169.
11. Bader, B.; Kuhn, K.; Owen, D. J.; Waldmann, H.; Wittinghofer, A.; Kuhlmann, J. Nature 2000, 403, 223-226. Kuhn, K.; Owen, D. J.; Bader, B.; Wittinghofer, A.; Kuhlmann, J.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 1023-1035.
12. Bader, B.; Kuhn, K.; Owen, D. J.; Waldmann, H.; Wittinghofer, A.; Kuhlmann, J. Nature 2000, 403, 223-226. Kuhn, K.; Owen, D. J.; Bader, B.; Wittinghofer, A.; Kuhlmann, J.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 1023-1035.
13. Kotzyba-Hibert, F.; Kapfer, I.; Goeldner, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1296-1312.
14. Kotzyba-Hibert, F.; Kapfer, I.; Goeldner, M. Angew. Chem. 1995, 107, 1391-1408.
15. Dormán, G.; Prestwich, G. D. TIBTECH 2000, 18, 64-77.
16. Kuhlmann, J.; Tebbe, A.; Völkert, M.; Wagner, M.; Uwai, K.; Waldmann, H. Angew. Chem. 2002, 114, 2655-2658; Angew. Chem., Int. Ed. 2002, 114, 2546-2550.
17. Kuhlmann, J.; Tebbe, A.; Völkert, M.; Wagner, M.; Uwai, K.; Waldmann, H. Angew. Chem. 2002, 114, 2655-2658; Angew. Chem., Int. Ed. 2002, 114, 2546-2550.
18. Hancock, J. F.; Magee, A. I.; Childs, J. E.; Marshall, C. J. Cell 1989, 57, 1167-1177.
19. Schroeder, H.; Leventis, R.; Rex, S.; Schelhaas, M.; Nägele, E.; Waldmann, H.; Silvius, J. R. Biochemistry 1997, 36, 13102-13109.
20. Waldmann, H.; Schelhaas, M.; Nägele, E.; Kuhlmann, J.; Wittinghofer, A.; Schroeder, H.; Silvius, J. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2238-2241.
21. Siddiqui, A. A.; Garland, J. R.; Dalton, M. B.; Sinensky, M. J. Biol. Chem. 1998, 273, 3712-3717.
22. Dormán, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661-5673.
23. Kale, T. A.; Raab, C.; Yu, N.; Dean, D. C.; Distefano, M. D. J. Am. Chem. Soc. 2001, 123, 4373-4381.
24. Turek, T. C.; Gaon, I.; Distefano, M. D.; Strickland, C. L. J. Org. Chem. 2001, 66, 3253-3264.
25. Gaon, I.; Turek, T. C.; Weller, V. A.; Edelstein, R. L.; Singh, S. K.; Distefano, M. D. J. Org. Chem. 1996, 61, 7738-7745. Marecak, D. M.; Horiuchi, Y.; Arai, H.; Shimonaga, M.; Maki, Y.; Koyama, T.; Ogura, K.; Prestwich, G. D. Bioorg. Med. Chem. Lett. 1997, 7, 1973-1978.
26. Gaon, I.; Turek, T. C.; Weller, V. A.; Edelstein, R. L.; Singh, S. K.; Distefano, M. D. J. Org. Chem. 1996, 61, 7738-7745. Marecak, D. M.; Horiuchi, Y.; Arai, H.; Shimonaga, M.; Maki, Y.; Koyama, T.; Ogura, K.; Prestwich, G. D. Bioorg. Med. Chem. Lett. 1997, 7, 1973-1978.
27. Spector, A. A. J. Lipid Res. 1975, 16, 165-179.
28. Choi, J.K., Ho, J., Curry, S., Qin, D., Bittman, R., Hamilton, J. A. J. Lipid Res. 2002, 43, 1000-1010.
29. Bar-Sagi, D.; Feramisco, J. R. Cell 1985, 42, 841-848.
30. Boguski, M. S.; McCormick, F. Nature 1993, 366. 643-654.
31. Boriack-Sjodin, P. A.; Margarit, S. M.; Bar-Sagi, D.; Kuriyan, J. Nature 1998, 394, 337-343.
32. Tucker, J.; Sczakiel, G.; Feuerstein, J.; John, J.; Goody, R. S.; Wittinghofer, A. EMBO J. 1986, 5, 1351-1358.
33. Schmidt, G.; Lenzen, C.; Simon, I.; Deuter, R.; Cool, R. H.: Goody, R. S.; Wittinghofer, A. Oncogene 1996, 12, 87-96.
34. Schmidt, G.; Wittinghofer, A. FEBS Lett. 2000, 474, 184-188.
35. Hall, B. E.; Yang, S. S.; Boriack-Sjodin, P. A.; Kuriyan, J.; Bar-Sagi, D. J. Biol. Chem. 2001, 276, 27629-27637.