Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11369-11374

  Ingenito, Raffaele ^a   Bianchi, Elisabetta ^a   Fattori, Daniela ^a   Pessi, Antonello ^a  

^a IRBM   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; DIAZOMETHANE; PEPTIDE; SULFONAMIDE; THIOESTER; THIOL DERIVATIVE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PROTEIN SYNTHESIS; SOLID STATE;

EID: 0033572729     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992668n     Document Type: Article

References (49)

1. (a) Blake, J. Int. J. Peptide Protein Res. 1981, 18, 383-392.
2. (b) Blake, J. Int. J. Peptide Protein Res. 1986, 27, 273-274.
3. (c) Yamashiro, D.; Li, C. H. Int. J. Peptide Protein Res. 1988, 31, 322-334.
4. (a) Mitin, Y. V.; Zapelova, N. P. Int. J. Peptide Protein Res. 1990, 35, 352-356.
5. (b) Mihara, H.; Maeda, S.; Kurosaki, R.; Ueno, S.; Sakamoto, S.; Niidome, T.; Hojo, H.; Aimoto, S.; Aoyagi, H. Chem. Lett. 1995, 5, 397-398.
6. (a) Schnolzer, M.; Kent, S. B. H. Science 1992, 256, 221-225.
7. (b) Baca, M.; Kent, S. B. H. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11638-11642
8. (c) Williams, M. J.; Muir, T. W.; Ginsberg, M. H.; Kent, S. B. H. J. Am. Chem. Soc. 1994, 116, 10797-10798.
9. (a) Dawson, P. E.; Kent, S. B. H. J. Am. Chem. Soc. 1993, 115, 7263-7266.
10. (b) Futaki, S.; Sogawa, K.: Maruyama, J.; Asahara, T.; Niwa, M. Tetrahedron Lett. 1997, 38, 6237-6240.
11. (c) Camarero, J. A.; Pavel, J.; Muir, T. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 347-349.
12. Zhang, L.; Tam, J. P. J. Am. Chem. Soc. 1997, 119, 2363-2370.
13. Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
14. Powers, J. C.; Kam, C.-M. Methods Enzymol. 1995, 248, 3-18.
15. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
16. Tam, J. P.; Lu, Y. A.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489.
17. Wilken, J.; Kent, S. B. H. Curr. Opin. Biotechnol. 1998, 9, 412-426.
18. (a) 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.
19. (b) Lu, W.; Starovasnik, M. A.; Kent, S. B. H. FEBS Lett. 1998, 429, 31-35.
20. (c) Wilken, J.; Hoover, D.; Thompson, D. A.; Barlow, P. N.; McSparrow, H.; Picard, L.; Wlodawer, A.; Lubkowski, J.; Kent, S. B. H. Chem. Biol. 1999, 6, 43-51.
21. (d) Kochendoerfer, G. G.; Salom, D.; Lear, J. D.; Wilk-Orescan, R.; Kent, S. B. H.; DeGrado, W. F. Biochemistry 1999, 38, 11905-11913.
22. (e) Sydor, J. R.; Herrmann, C.; Kent, S. B. H.; Goody, R.; Engelhard, M. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 7865-7870.
23. (a) Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadiri, M. R. Nature 1996, 382, 525-528.
24. (b) Severin, K.; Lee, D. H.; Kennan, A. J.; Ghadiri, M. R. Nature 1997, 389, 706-709.
25. (c) Lee, D. H.; Garnja, J. A.; Severin, K.; Yokobayashi, Y.; Ghadiri, M. R. Nature 1997, 390, 591-594.
26. (e) Yao, S.; Ghosh. I.; Zutshi, R.; Chmielewski, J. J. Am. Chem. Soc. 1997, 119, 10559-10560.
27. (f) Yao, S.; Ghosh, I.; Zutshi, R.; Chmielewski, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 478-481.
28. (g) Yao, S.; Ghosh, I.; Zutshi, R.; Chmielewski, J. Nature 1998, 396, 447-450.
29. Canne, L. E.: Bark, S. J.; Kent, S. B. H. J. Am. Chem. Soc. 1996, 118, 5891-5896. In this work ligation is shown to be possible for both the X-Gly and the Gly-X junctions
30. Zhang, L.; Tam, J. P. Tetrahedron Lett. 1996, 38, 3-6.
31. Tam, J. P.; Yu, Q. Biopolymers 1998, 46, 319-327.
32. Beligere, G. S.; Dawson, P. E. J. Am. Chem. Soc. 1999, 121, 6332-6333.
33. (a) Camarero, J. A.; Cotton, G. J.; Adeva, A.; Muir, T. W. J. Peptide Res. 1998, 51, 303-316.
34. (b) Canne, L. E.; Botti, P.; Simon, R. J.; Chen, Y.; Dennis, E. A.; Kent, S. B. H. J. Am. Chem. Soc. 1999, 121, 8720-8727.
35. Hojio, H.; Aimoto, S. Bull Chem. Soc. Jpn. 1991, 64, 111-117.
36. Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269-1270.
37. Canne, L. E.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217-1220.
38. Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U.S.A. 1999, 10068-10073.
39. Li, X.; Kawakami, T.; Aimoto, S. Tetrahedron Lett. 1998, 39, 8669-8672.
40. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1971, 636-637.
41. Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
42. Backes, B. J.; Ellman, J. A. J. Org. Chem. 1999, 64, 2322-2330.
43. 5,15,18-21 (27) The resins used in our experiments were PEG-PS (Perkin-Elmer Perseptive), NovaSyn TG (NovaBiochem), and the already functionalized 3-carboxypropanesulfonamide-polystyrene (NovaBiochem).
44. Atherton, E.; Sheppard, R. C. Solid-phase peptide synthesis, a practical approach; IRL Press: Oxford, 1989.
45. 28 However, for all the peptides included in this study we used Reagent B (Sole, N. A.; Barany, G. J. Org. Chem. 1992, 57, 5399-5403) i.e., TFA-phenol-water-trisopropylsilane (88 5:5:2) and a cleavage time of 1.5 h.
46. a = 10 (F. G. Bordwell Acc. Chem. Res. 1988, 21, 456-463). The thiophenol produced through the exchange is expected to immediately lose its proton, thus regenerating the thiophenate anion.
47. Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
48. 31 α-benzyl thioesters have also been prepared with the same procedure.
49. Bianchi, E.; lngenito, R.; Simon, R. J.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 7698-7699.