Photoactive analogs of farnesyl pyrophosphate containing benzoylbenzoate esters: Synthesis and application to photoaffinity labeling of yeast protein farnesyltransferase

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7738-7745

  Gaon, Igor ^a   Turek, Tammy C ^a   Weller, Valerie A ^a   Edelstein, Rebecca L ^a   Singh, Satinder K ^a   Distefano, Mark D ^a  

^a University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; FARNESYL DIPHOSPHATE; PROTEIN FARNESYLTRANSFERASE; TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME BINDING; PHOTOAFFINITY LABELING; PHOTOCHEMISTRY; YEAST;

EID: 0029849785     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9602736     Document Type: Article

References (26)

1. Chowdhry, V.; Westheimer, F. H. Ann. Rev. Biochem. 1979, 48, 293-325.
2. Burnner, J. Ann. Rev. Biochem. 1993, 62, 483-514.
3. (b) Fleming, S. A. Tetrahedron 1995, 51, 12479-12520.
4. (a) Goldstein, J.; Brown, M. S. Nature 1990, 343, 425-430.
5. (b) Sinensky, M.; Lutz, R. J. BioEssays 1992, 14, 25-31.
6. (a) Buss, J. E.; Marsters, J. C. Chem. Biol. 1995, 2, 787-791.
7. (b) Gibbs, J. B.; Oliff, A.; Kohl, N. E. Cell 1994, 77, 175-178.
8. (c) Tamanoi, F. TIBS 1993, 18, 349-353.
9. (a) Das, N. P.; Allen, C. M. Biochem. Biophys. Res. Commun. 1991, 181, 729-735.
10. (b) Omer, C. A.; Kral, A. M.; Diehl, R. E.; Prendergast, G. C.; Powers, S.; Allen, C. M.; Gibbs, J. B.; Kohl, N. E. Biochemistry 1993, 32, 5167-5176.
11. (c) Yokoyama, K.; McGeady, P.; Gelb, M. H. Biochemistry 1995, 34, 1344-1354.
12. (d) Bukhtiyarov, Y. E.; Omer, C. A.; Allen, C. M. J. Biol. Chem. 1995, 270, 19035-19040.
13. (a) Baba, T.; Allen, C. M. Biochemistry 1984, 23, 1312-1322.
14. (b) Baba, T.; Muth, J.; Allen, C. M. J. Biol. Chem. 1985, 260, 10467-10473.
15. Chowdhry, V.; Vaughan, R.; Westheimer, F. H. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 1406-1408.
16. Dorman, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661-5673.
17. Ying, W.; Sepp-Lorenzino, L.; Cai, K.; Aloise, P.; Coleman, P. S. J. Biol. Chem. 1994, 269, 470-477.
18. Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526-5527.
19. Davisson, V. J.; Woodside, A. B.; Poulter, C. D. Methods Enzymol. 1985, 110, 130-144.
20. (a) Bond, P. D.; Dolence, J. M.; Poulter, C. D. Methods Enzymol. 1995, 250, 30-43.
21. (b) Pompliano, D. L.; Gomez, R. P.; Anthony, N. J. J. Am. Chem. Soc. 1992, 114, 7945-7946.
22. Brown, M. J.; Milano, P. D.; Lever, D. C.; Epstein, W. W.; Poulter, C. D. J. Am. Chem. Soc. 1991, 113, 3176-3177.
23. Dolence, J. M.; Cassidy, P. B.; Mathis, J. R.; Poulter, C. D. Biochemistry 1995, 34, 16687-16694.
24. Barany, G.; Merrifield, R. B. In The Peptides; Academic Press: New York, 1979; Vol. 2; pp 1-284.
25. Mayer, M. P.; Prestwich, G. D.; Dolence, J. M.; Bond, P. D.; Wu, H.-y.; Poulter, C. D. Gene 1993, 132, 41-47.
26. Reed, B. C.; Rilling, H. C. Biochemistry 1976, 15, 3739-3745.