Lactone and lactam library synthesis by silver ion-assisted orthogonal cyclization of unprotected peptides

Journal of the American Chemical Society

Volumn 121, Issue 14, 1999, Pages 3311-3320

  Zhang, Lianshan ^a,b   Tam, James P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Sphinx Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM; LACTONE; PEPTIDE; PEPTIDE LIBRARY; SILVER;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; ENTHALPY; ENTROPY; OLIGOMERIZATION; PH; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN STRUCTURE; SYNTHESIS;

EID: 0033553118     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983859d     Document Type: Article

References (73)

1. (a) Hruby, V. J. Life Sci. 1982, 31, 189-199.
2. (b) Hruby, V. J. Trends Pharm. Sci. 1985, 6, 259-262.
3. (c) Al-Obeidi, F.; Castrucci; A. M. del L.; Hadley, M. E.; Hruby, V. J. J. Med Chem. 1989, 32, 2555-2561.
4. (a) Blout, E. R. Biopolymers 1981, 20, 1901-1912.
5. (b) Kessler, H. Angew. Chem. 1986, 25, 997-999.
6. Karle, I. L. Biopolymers 1996, 40, 157-180.
7. Rizo, J.; Gierasch, L. M. Annu. Rev. Biochem. 1992, 61, 387-418.
8. (a) Cwirla, S. E.; Balasubramanian, P.; Duffin D. J.; Wagstrom, C. R.; Gates, C. M.; Singer, S. C.; Davis, A. M.; Tansik, R. L.; Mattheakis, L. C.; Boytos, C. M.; Schatz, P. J.; Baccanari, D. P.; Wrighton, N. C.; Barrett, R. W.; Dower, W. J. Science 1997, 276, 1696-1699.
9. (b) Wrighton, N. C.; Farrell, F. X.; Chang, R.; Kashyap, A. K.; Barbone, F. P.; Mulcahy, L. S.; Johnson, D. L.; Barrett, R. W.; Jolliffe, L. K.; Dower, W. J. Science 1996, 273, 458-464.
10. Spatola, A. F.; Crozet, Y. J. Med. Chem. 1996, 39, 3842-3846.
11. (a) Zhang, L.; Tam, J. P. J. Am. Chem. Soc. 1997, 119, 2363-2370.
12. (b) Spetzler, J.; Tam, J. P. Pept. Res. 1996, 9, 290-6;
13. (c) Pallin, T. D.; Tam, J. P. Chem. Commun. 1996, 1345-1346.
14. (a) Robey, F. A.; Fields R. L. Anal. Biochem. 1989, 177, 373-377.
15. (b) Tolman, R. L.; Bednarek, M. A.; Johnson, B. A.; Leanza, W. J.; Marburg, S.; Underwood, D. J.; Emini, E. A.; Conley, A. J. Int. J. Pept. Protein Res. 1993, 41, 455-466.
16. (c) Conley, A. J.; Conard, P.; Bondy, S.; Dolan, C. A.; Hannah, J.; Leanza, W. J.; Marburg, S.; Rivetna, M.; Rusiecki, V. K.; Sugg, E. E.; et al. Vaccine 1994, 12, 445-451.
17. Aston, K. W.; Henke, S. L.; Modak, A. S.; Riley, D. P.; Sample, K. R.; Weiss, R. H.; Neumann, W. L. Tetrahedron Lett. 1994, 35, 3687-3690.
18. (a) Manesis, N. J.; Goodman, M. J. Org. Chem. 1987, 52, 5331-5341.
19. (b) Gilon, C.; Halle, D.; Chorev, M.; Selinger, Z.; Byk, G. Biopolymers 1991, 31, 745-750.
20. (a) McMurray, J. S. Tetrahedron Lett. 1992, 33, 4557-4560.
21. (b) Kates, S. A.; Sole, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552.
22. (c) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550.
23. (a) Schiller, P. W.; Nguyen, T. M.-D.; Miller, J. Int. J. Pept. Protein Res. 1985, 25, 171-177.
24. (b) Felix, A. M.; Wang, C. T.; Heimer, E. P.; Fournier, A. J. Int. J. Pept. Protein Res. 1988, 31, 231-238.
25. (c) Ehrlich, A.; Heyne, H. U.; Winter, R.; Beyermann, M.; Haber, H.; Carpino L. A.; Bienert, M. J. Org. Chem. 1996, 61, 8831-8838.
26. Jackson, D. Y.; Burnier, J. P.; Wells, J. A. J. Am. Chem. Soc. 1995, 117, 819-820.
27. Botti, P.; Pallin, D. P.; Tam, J. P. J. Am. Chem. Soc. 1996, 118, 10018-10024.
28. (a) Tam, J. P.; Lu, Y.-A. Tetrahedron Lett. 1998, 7, 1583-1592.
29. (b) Tam, J. P.; Lu, Y.-A. Protein Sci. 1998, 7, 1583-1592.
30. (a) Tam, J. P.; Yu, Q. Biopolymers 1998, 46, 319-327.
31. (b) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
32. (c) Camarero, J. A.; Muir, T. W. Chem. Commun. 1997, 1369-1370.
33. (d) Camarero, J. A.; Muir, T. W. In Peptides Chemistry, Structure and Biology, Proceedings of the 15th American Peptide Symposium; Tam, J. P., Kaumaya, P. T. P., Eds.; in press.
34. (a) Kemp, D. S. Biopolymers 1981, 20, 1793-1804.
35. (b) Fotouhi, N.; Galakatos, N.; Kemp, D. S. J. Org. Chem. 1989, 54, 2803-2817.
36. (c) Kemp, D. S.; Carey, R. I. Tetrahedron Lett. 1991, 32, 2845-2848.
37. (d) Kemp, D. S.; Carey, R. I. J. Org. Chem. 1993, 58, 2216-2222.
38. (a) Liu, C. F.; Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6584-6588.
39. (b) Liu, C. F.; Tam, J. P. J. Am. Chem. Soc. 1994, 116, 4149-4153.
40. (a) Tam, J. P., Lu, Y.-A.; Liu, C. F.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489.
41. (b) Dawson, P. E.; Kent, S. B. H. J. Am. Chem. Soc. 1993, 115, 7263-7266.
42. (a) Schwyzer, R.; Hürlimann, C. Helv. Chim. Acta. 1954, 37, 155-166.
43. (b) Boopsingh, B.; Satchell, D. P. N. J. Chem. Soc., Perkin Trans. 1978, 2, 23.
44. (c) Nambu, Y.; Endo, T.; Okawara, M. Bull. Chem. Soc. Jpn. 1981, 54, 3433.
45. (a) Blake, J.; Li, C. H. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4055-4058.
46. (b) Yamashiro, D.; Li, C. H. Int. J. Pept. Protein Res. 1988, 31, 322-334.
47. (c) Hojo, H.; Aimoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 111-117.
48. Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1974, 57, 2661-2663.
49. Masamune, S.; Kamata, S.; Schilling, W. J. Am. Chem. Soc. 1975, 97, 3515-3516.
50. Zhang, L.; Tam, J. P. Tetrahedron Lett. 1997, 38, 4375-4378.
51. Wieland, T.; Bokelmann, E.; Bauer, L.; Lang, H. U.; Lau, H. Liebigs Ann. Chem. 1953, 583, 129-149.
52. Sanger, F. Biochem. J. 1945, 39, 507-515.
53. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70-77.
54. (a) Hotchkiss, R. D.; Dubos, R. J. J. Biol. Chem. 1940, 136, 803-804.
55. (b) Wieland, T., Naturwissenschaften 1987, 74, 367-373.
56. (c) Wieland, T.; Lüben, G.; Ottenheym, H. C. J.; Faesel, J.; de Vires, J. X.; Konz, W.; Prox, A.; Schmid, J. Angew. Chem., Int. Ed. Engl. 1968, 7, 204-208.
57. (a) Belew, M.; Porath, J. J. Chromatogr. 1990, 516, 333-354.
58. (b) Sigel, H.; Martin, R. B. Chem. Rev. 1982, 82, 385-426.
59. (a) Richardson, J. S.; Richardson, D. C. Science 1988, 240, 1648-1652.
60. (b) Chakrabartty, A.; Doig, A. J.; Baldwin, R. L. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11332-11336.
61. (c) Kamtekar, S.; Schiffer, J. M.; Xiong, H.; Babik, J. M.; Hecht, M. H. Science 1993, 262, 1680-1685.
62. (a) Gurrath, M.; Müller, G.; Kessler, H.; Aumailley, M.; Timpl, R. Eur. J. Biochem. 1992, 210, 911-921.
63. (b) Müller, G.; Gurrath, M.; Kessler, H.; Timpl, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 326-328.
64. (a) Morita, H.; Kayashita, T.; Shishido, A.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1996, 52, 1165-1176.
65. (b) Morita, H.; Shishido, A.; Kayashita, T.; Takeya. K.; Itokawa, H. J. Nat. Prod. 1997, 60, 404-407.
66. Rapp, W.; Zhang, L.; Bayer, E. In Innovation and Perspective in Solid-Phase Synthesis, Peptides, Polypeptides and Oligonucleotides; Epton, R., Ed.; SPCC (UK) Ltd.: Birmingham, 1990; p 205.
67. Ostresh, J. M.; Winkle, J. H.; Hamashin, V. T.; Houghten, R. A. Biopolymers 1994, 34, 1681.
68. Zhang, L.; Tam, J. P. Tetrahedron Lett. 1997, 38, 3-6.
69. (a) Dale, J. Angew. Chem. 1966, 78, 1070.
70. (b) Kessler, H.; Kutscher, B. Liebigs Ann. Chem. 1986, 869.
71. (c) Kessler, H.; Kutscher, B. Liebigs Ann. Chem. 1986, 914.
72. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
73. Marfey, P. Carlsberg Res. Commun. 1984, 591-596.