Chemical protein synthesis by solid phase ligation of unprotected peptide segments

Journal of the American Chemical Society

Volumn 121, Issue 38, 1999, Pages 8720-8727

  Canne, Lynne E ^a,d   Botti, Paolo ^d   Simon, Reyna J ^b,d   Chen, Yijun ^c,d   Dennis, Edward A ^c,d   Kent, Stephen B H ^d  

^a EXELIXIS INC   (United States)

^b IntraBiotics Pharmaceuticals Inc   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Gryphon Therapeutics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; PEPTIDE; PHOSPHOLIPASE A2; POLYMER; POLYPEPTIDE; PROTEIN;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTEIN SYNTHESIS;

EID: 0033615313     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9836287     Document Type: Article

References (45)

1. (a) Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-225.
2. (b) Liu, C. F.; Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6584-6588.
3. (c) Rose, K. J. Am. Chem. Soc. 1994, 116, 30-34.
4. (d) Muir, T. W.; Williams, M. J.; Ginsberg, M. H.; Kent, S. B. H. Biochemistry 1994, 33, 7701-7708.
5. (e) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
6. Wilken, J.; Kent, S. B. H. Curr. Opin. Biotechnol. 1998, 9, 412-426.
7. (a) Williams, M. J.; Muir, T. W.; Ginsberg, M. H.; Kent, S. B. H. J. Am. Chem. Soc. 1994, 116, 10797-10798.
8. (b) Lu, W.; Qasim, M. A,; Kent, S. B. H. J. Am. Chem. Soc. 1996, 118, 8518-8523.
9. (c) Smith, R.; Brereton, I. M.; Chai, R. Y.; Kent, S. B. H. Nature Struct. Biol. 1996, 3, 946-950.
10. (d) Hackeng, T. M.; Mounier, C. M.; Bon, C.; Dawson, P. E.; Griffin, J. H.; Kent, S. B. H. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7845-7850.
11. (e) Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
12. (f) Lu, W.; Qasim, M. A.; Laskowski, M., Jr.; Kent, S. B. H. Biochemistry 1997, 36, 673-679.
13. (g) Lu, W.; Starovasnik, M. A.; Kent, S. B. H. FEBS Lett. 1998, 429, 31-35.
14. (h) Wilken, J.; Hoover, D.; Thompson, D. A.; Barlow, P. N.; McSparron, H.; Picard, L.; Wlodawer, A.; Lubkowski, J.; Kent, S. B. H. Chem. Biol. 1999, 6, 43-51.
15. (i) Bolin, K. A.; Anderson, D. J.; Trulson, J. A.; Gantz, I.; Thompson, D. A.; Wilken, J.; Kent, S. B. H.; Milhauser, G. L. FEBS Lett., 1999, 451, 125-131.
16. (a) Baca, M.; Muir, T. W.; Schnölzer, M.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 1881-87.
17. (b) Ueda, H.; Siani, M. A.; Gong, W.; Thompson, D. A.; Brown, G. G.; Wang, J. M. J. Biol. Chem. 1997, 272, 24966-24960.
18. (c) Campbell, J. J.; Hendrick, J.; Zlotnik, A.; Siani, M. A.; Thompson, D. A.; Butcher, E. C. Science 1998, 279, 381-384.
19. (d) Dealwis, C.; Fernandez, E. J.; Thompson, D. A.; Simon, R. J.; Siani, M. A.; Lolis, E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6941-6946.
20. (a) Rau, H. K.; Haehnel, W. J. Am. Chem. Soc. 1998, 120, 468-476.
21. (b) Figliozzi, G. M.; Siani, M. A.; Canne, L. E.; Robson, B.; Simon, R. J. Abstracts of Papers, 24th Symposium of the European Peptide Society, Edinburgh, Scotland; European Peptide Society: Swansea, U.K., 1996; p 202.
22. (c) Love, S. G.; Englebretsen, D. R.; Garnham, B.; Cavanagh, A. C.; Morton, H.; Chernushevich, I. C.; Standing, K. G.; Alewood, P. F. NATO Series on Molecular Aggregates 1996.
23. (a) Zhang, L.; Tam, J. P. J. Am. Chem. Soc. 1997, 119, 2363-2370.
24. (b) Camarero, J. A.; Pavel, J.; Muir, T. W. Angew. Chem., Int. Ed. 1998, 37, 347-349.
25. Canne, L. E.; Winston, R. L.; Kent, S. B. H. Tetrahedron Lett. 1997, 38, 3361-3364.
26. Protecting Groups in Organic Synthesis, 2nd ed.; Greene, T. W., Wuts, P. G. M., Eds.; John Wiley & Sons: New York, 1991.
27. Canne, L. E.; Ferré-D'Amaré, A. R.; Burley, S. K.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 2998-3007.
28. αCOSH; the sequence of the C-terminal segment was CADPSEEWVQKYVSDLELSA.
29. Mollison, K. W.; Mandecki, W.; Zuiderweg, E. R. P.; Fayer, L.; Fey, T. A.; Krause, R. A.; Conway, R. G.; Miller, L.; Edalji, R. P.; Shallcross, M. A.; Lane, B.; Fox, J. L.; Greer, J.; Carter, G. W. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 292-296.
30. αCOSH. The sequence of C5a(47-74) was CIKAF-TECCVVASQLRANISHKDMQLGR.
31. Bernhagen, J.; Mitchell, R. A.; Calandra, T.; Voelter, W.; Cerami, A.; Bucala, R. Biochemistry 1994, 33, 14144-14155.
32. αCOSW. The sequence of MIF(81-115) was CGLLAERLRISP-DRVYINYYDMNAASVGWNNSTFA.
33. Balboa, M. A.; Balsinde, J.; Winstead, M. V.; Tischfield, J. A.; Dennis, E. A. J. Biol. Chem. 1996, 271, 32381-32384.
34. Dennis, E. A. TrendsBiochem. Sci. 1999, 22, 1-2; Chen, Y.; Dennis E. A. Biochim. Biophys. Acta 1998, 1394, 57-64.
35. Dennis, E. A. TrendsBiochem. Sci. 1999, 22, 1-2; Chen, Y.; Dennis E. A. Biochim. Biophys. Acta 1998, 1394, 57-64.
36. Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
37. Merrifield, R.B. Science 1986, 232, 341-347.
38. Kent, S. B. H. Annu. Rev. Biochem. 1998, 57, 957-984.
39. To date, the largest polypeptide synthesized by the SPCL method described above has involved the chemical ligation of seven unprotected peptide segments to give a product of 28 kDa (Wuyuan Lu, personal communication).
40. Xu, R.; Ayers, B.; Cowburn, D.; Muir, T. W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 388-393.
41. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, 180-193.
42. (a) Hojo, H.; Aimoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 111-117.
43. (b) Hojo, H.; Kwon, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-06.
44. (a) Yamashiro, D.; Li, C. H. Int. J Pept. Protein Res. 1988, 31, 322-34.
45. (b) Canne, L. E.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217-1220.