Solid-phase synthesis, mass spectrometric analysis of the zinc-folding, and phorbol ester-binding studies of the 116-mer peptide containing the tandem cysteine-rich C1 domains of protein kinase C gamma

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 6, 1999, Pages 1213-1221

  Fukuda, Hiroyuki ^a   Irie, Kazuhiro ^b   Nakahara, Akifumi ^b   Ohigashi, Hajime ^b   Wender, Paul A ^c  

^a Nihon PerSeptive Ltd   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c STANFORD UNIVERSITY   (United States)

Author keywords

Cysteine rich domain; Phorbol ester; Protein kinase C; Zinc finger

Indexed keywords

AMINO ACID; CYSTEINE DERIVATIVE; PEPTIDE; PHORBOL ESTER; PROTEIN KINASE C; ZINC FINGER PROTEIN;

ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; NEURALGIA; NONHUMAN; SCATCHARD PLOT; SIGNAL TRANSDUCTION; SOLID PHASE EXTRACTION; STOICHIOMETRY; TUMOR PROMOTION;

AMINO ACID SEQUENCE; BINDING SITES; CYSTEINE; ISOENZYMES; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDES; PHORBOL 12,13-DIBUTYRATE; PROTEIN CONFORMATION; PROTEIN ENGINEERING; PROTEIN KINASE C; TRITIUM; ZINC FINGERS;

EID: 0032974404     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00037-1     Document Type: Article

References (37)

1. For recent reviews, see: Houssa, B.; van Blitterswijk, W. J. Biochem. J. 1998, 331, 677-680; Hurley, J. H.; Grobler, J. A. Curr. Opin. Struct. Biol. 1997, 7, 557-565; Quest, A. F. G. Enzyme Protein 1996, 49, 231-261; Srinivasan, N.; Bax, B.; Blundell, T. L.; Parker, P. J. Proteins: Struct. Funct., and Genet. 1996, 26, 217-235.
2. For recent reviews, see: Houssa, B.; van Blitterswijk, W. J. Biochem. J. 1998, 331, 677-680; Hurley, J. H.; Grobler, J. A. Curr. Opin. Struct. Biol. 1997, 7, 557-565; Quest, A. F. G. Enzyme Protein 1996, 49, 231-261; Srinivasan, N.; Bax, B.; Blundell, T. L.; Parker, P. J. Proteins: Struct. Funct., and Genet. 1996, 26, 217-235.
3. For recent reviews, see: Houssa, B.; van Blitterswijk, W. J. Biochem. J. 1998, 331, 677-680; Hurley, J. H.; Grobler, J. A. Curr. Opin. Struct. Biol. 1997, 7, 557-565; Quest, A. F. G. Enzyme Protein 1996, 49, 231-261; Srinivasan, N.; Bax, B.; Blundell, T. L.; Parker, P. J. Proteins: Struct. Funct., and Genet. 1996, 26, 217-235.
4. For recent reviews, see: Houssa, B.; van Blitterswijk, W. J. Biochem. J. 1998, 331, 677-680; Hurley, J. H.; Grobler, J. A. Curr. Opin. Struct. Biol. 1997, 7, 557-565; Quest, A. F. G. Enzyme Protein 1996, 49, 231-261; Srinivasan, N.; Bax, B.; Blundell, T. L.; Parker, P. J. Proteins: Struct. Funct., and Genet. 1996, 26, 217-235.
5. Hurley, J. H.; Newton, A. C.; Parker, P. J.; Blumberg, P. M.; Nishizuka, Y. Protein Science 1997, 6, 477-480.
6. Ono, Y.; Fujii, T.; Igarashi, K.; Kuno, T.; Tanaka, C.; Kikkawa, U.; Nishizuka, Y. Proc. Natl. Acad. Sci. USA 1989, 86, 4868-4871.
7. Burns, D. J.; Bell, R. M. J. Biol. Chem. 1991, 266, 18330-18338.
8. Ishii, H.; Jirousek, M. R.; Koya, D.; Takagi, C.; Xia, P.; Clermont, A.; Bursell, S.-E.; Kern, T. S.; Ballas, L. M.; Heath, W. F.; Stramm, L. E.; Feener, E. P.; King, G. L. Science 1996, 272, 728-731.
9. Malmberg, A. B.; Chen, C.; Tonegawa, S.; Basbaum, A. I. Science 1997, 278, 279-283.
10. Geiger, T.; Müller, M.; Dean, N. M.; Fabbro, D. Anti-Cancer Drug Design 1998, 13, 35-45.
11. Hommel, U.; Zurini, M.; Luyten, M. Nat. Struct. Biol. 1994, 1, 383-387.
12. Ichikawa, S.; Hatanaka, H.; Takeuchi, Y.; Ohno, S.; Inagaki, F. J. Biochem. 1995, 117, 566-574.
13. Xu, R. X.; Pawelczyk, T.; Xia, T.-H.; Brown, S. C. Biochemistry 1997, 36, 10709-10717.
14. Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924.
15. Kazanietz, M. G.; Wang, S.; Milne, G. W. A.; Lewin, N. E.; Liu, H. L.; Blumberg, P. M. J. Biol. Chem. 1995, 270, 21852-21859.
16. Szallasi, Z.; Bogi, K.; Gohari, S.; Biro, T.; Acs, P.; Blumberg, P. M. J. Biol. Chem. 1996, 271, 18299-18301.
17. Hunn, M.; Quest, A. F. G. FEBS Lett. 1997, 400, 226-232.
18. Wender, P. A.; Irie, K.; Miller, B. L. Proc. Natl. Acad. Sci. USA 1995, 92, 239-243.
19. Irie, K.; Yanai, Y.; Ohigashi, H.; Wender, P. A.; Miller, B. L. Bioorg. Med. Chem. Lett. 1996, 6, 353-356.
20. Yanai, Y.; Irie, K.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1997, 7, 117-122.
21. Irie, K.; Yanai, Y.; Oie, K.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1997, 7, 965-970.
22. Irie, K.; Yanai, Y.; Oie, K.; Ishizawa, J.; Nakagawa, Y.; Ohigashi, H.; Wender, P. A.; Kikkawa, U. Bioorg. Med. Chem. 1997, 5, 1725-1737.
23. Irie, K.; Oie, K.; Nakahara, A.; Yanai, Y.; Ohigashi, H.; Wender, P. A.; Fukuda, H.; Konishi, H.; Kikkawa, U. J. Am. Chem. Soc. 1998, 120, 9159-9167.
24. Quest, A. F. G.; Bell, R. M. J. Biol. Chem. 1994, 269, 20000-20012.
25. Bowers, B. J.; Parham, C. L.; Sikela, J. M.; Wehner, J. M. Gene 1993, 123, 263-265.
26. Fukuda, H.; Irie, K.; Nakahara, A.; Oie, K.; Ohigashi, H.; Wender, P. A. Tetrahedron Lett. 1998, 39, 7943-7946.
27. Sharkey, N. A.; Blumberg, P. M. Cancer Res. 1985, 45, 19-24.
28. Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279-2282.
29. The stepwise solid-phase synthesis of the 104-mer peptide, see: Mascagni, P.; Sia, D. Y.; Coates, A. R. M.; Gibbons, W. A. Tetrahedron Lett. 1990, 31, 4637-4640.
30. Hubbard, S. R.; Bishop, W. R.; Kirschmeier, P.; George, S. J.; Cramer, S. P.; Hendrickson, W. A. Science 1991, 254, 1776-1779.
31. Quest, A. F. G.; Bloomenthal, J.; Bardes, E. S. G.; Bell, R. M. J. Biol. Chem. 1992, 267, 10193-10197.
32. For a review, see: Loo, J. A. Mass Spec. Rev. 1997, 16, 1-23.
33. Fabris, D.; Zaia, J.; Hathout, Y.; Fenselau, C. J. Am. Chem. Soc. 1996, 118, 12242-12243.
34. Konrat, R.; Weiskirchen, R.; Bister, K.; Kreutler, B. J. Am. Chem. Soc. 1998, 120, 7127-7128.
35. Witkoska, H. E.; Shackleton, C. H. L.; Dahlman-Wright, K.; Kim, J. Y.; Gustafsson, L. J. Am. Chem. Soc. 1995, 117, 3319-3324.
36. Dimitrijevic, S. M.; Ryves, W. J.; Parker, P. J.; Evans, F. J. Mol. Pharmacol. 1995, 48, 259-267.
37. Kazanietz, M. G.; Areces, L. B.; Bahador, A.; Mischak, H.; Goodnight, J.; Mushinski, J. F.; Blumberg, P. M. Mol. Pharmacol. 1993, 44, 298-307.