Thia zip reaction for synthesis of large cyclic peptides: Mechanisms and applications

Journal of the American Chemical Society

Volumn 121, Issue 18, 1999, Pages 4316-4324

  Tam, James P ^a   Lu, Yi An ^a   Yu, Qitao ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BUFFER; CYCLOPEPTIDE; CYCLOPSYCHOTRIDE; CYSTEINE DERIVATIVE; DEFENSIN; DISULFIDE; LACTAM; THIOESTER; THIOLACTONE; UNCLASSIFIED DRUG; UREA;

ACYLATION; AMINO ACID SEQUENCE; ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; CYCLIZATION; DENATURATION; DISULFIDE BOND; ESCHERICHIA COLI; ESTERIFICATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PEPTIDE SYNTHESIS; PH; PSEUDOMONAS AERUGINOSA; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0033549108     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984480u     Document Type: Article

References (81)

1. (a) Nicolaou, K. C. Tetrahedron 1977, 33, 683-710.
2. (b) Stach, H.; Hesse, M. Tetrahedron 1988, 44, 1573-1590.
3. (a) Ognyanov, V.; Hesse, M. Helv. Chim. Acta 1989, 72, 1522-1526.
4. (b) Stefan, B.; Hesse, M. Helv. Chim. Acta 1987, 70, 1333-1340.
5. (c) Koch, T.; Hesse, M. Synthesis 1995, 251-252.
6. (d) Ivancev, W.; Ognyanov, V.; Vassil, I.; Hesse, M. Tetrahedron 1996, 52, 4363-4376.
7. (a) Borchardt, A.; Still, W. C. Synlett. 1995, 539-540.
8. (b) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1993, 115, 3328-3329.
9. (c) Matsuyama, H.; Nakamura, T.; Takatsuka, A.; Kobayashi, M.; Kamigata, N. Chem. Lett. 1988, 1931-1932.
10. (a) Tochtermann, W.; Kraft, P. Synlett 1996, 1029-1035.
11. (b) Dowd, P.; Choi, S. C. Tetrahedron Lett. 1991, 32, 565-568.
12. (c) Takeuchi, H.; Matsushita, Y.; Yuli, E. J. Org. Chem. 1991, 56, 1535-1537. (d)
13. (a) Guggisberg, A.; Dabrowski, B.; Kramer, U.; Heidelberger, C.; Hesse, M.; Schmid, H. Helv. Chim. Acta 1978, 61, 1039-1049.
14. (b) Kramer, U.; Guggisberg, A.; Hesse, M.; Schmid, H. Helv. Chim. Acta 1978, 61, 1342-1352.
15. (a) Kramer, U.; Guggisberg, A.; Hesse, M.; Schmid, H. Angew. Chem., Int. Ed. Engl. 1977, 16, 861-862.
16. (b). Kramer, U.; Guggisberg, A.; Hesse, M.; Schmid, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 200-202.
17. Liu, C.-F.; Tam, J. P. J. Am. Chem. Soc. 1994, 116, 4149-4153.
18. (b) Liu, C-.F.; Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6584-6588.
19. Botti, P.; Pallin, T. D.; Tam, J. P. J. Am. Chem. Soc. 1996, 118, 10018-10024.
20. Zhang, L.; Tam, J. P. J. Am. Chem. Soc. 1997, 119, 2363-2370.
21. Zhang, L.; Tam, J. P. Tetrahedron Lett. 1997, 38, 4375-4378.
22. (a) Tam, J.P.; Lu ,Y.-A. Protein Sci. 1998, 7, 1583-1592.
23. (b) Tam, J. P.; Lu, Y.-A. Tetrahedron Lett. 1997, 38, 5599-5602.
24. (a) Camarero, J. A.; Muir, T. W. Chem. Commun. 1997, 1369-1370.
25. (b) Camarero, J. A.; Joanna, P.; Muir, T. W. Angew. Chem., Int. Ed. 1998, 37, 347-349.
26. (c) Shao, Y.; Lu, W.; Kent, B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
27. Valters, R. E.; Fulop, F.; Korbonits, D. Advances In Heterocyclic Chemistry; Academic Press: New York, 1995; Vol. 64, pp 251-321.
28. Fulop, F. Acta Chim. Hung., Models Chem. 1994, 131, 697.
29. (a) Hruby, V. J. Life Sci. 1982, 31, 189-199.
30. (b) Hruby, V. J. Trends Pharm. Sci. 1985, 6, 259-262.
31. (c) Al-Obeidi, F.; Castrucci, A. M. del L.; Hadley, M. E.; Hruby, V. J. J. Med. Chem. 1989, 32, 2555-2561.
32. (a) Manesis, N. J.; Goodman, M. J. Org. Chem. 1987, 52, 5331-5341.
33. (b) Gilon, C.; Halle, D.; Chorev, M.; Selinger, Z.; Byk, G. Biopolymers 1991, 31, 745-750.
34. (c) McMurray, J. S. Tetrahedron Lett. 1992, 33, 4557-4560.
35. (d) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550.
36. (e) Kates, S. A.; Sole, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552
37. (a) Schiller, P. W.; Nguyen, T. M. D.; Miller, J. Int. J. Pept. Protein Res. 1985, 25, 171-177.
38. (b) Felix, A. M.; Wang, C. T.; Heimer, E. P.; Fournier, A. J. Int. J. Pept. Protein Res. 1988, 31, 231-238.
39. (c) Ehrlich, A.; Heyne, H. U.; Winter, R.; Beyermann, M.; Haber, H.; Carpino, L. A.; Bienert, M. J. Org. Chem. 1996, 61, 8831-8838.
40. (a) Witherup, K. M.; Bogusky, M. J.; Anderson, P. S.; Ramjit, H.; Ransom, R. W.; Wood, T.; Sardana, M. J. Natl. Prod. 1994, 57, 1619-1625.
41. (b) Gustafson, K. R.; Sowder, R. C., II; Henderson, L. E.; Parsons, I. C.; Kashman, Y.; Cardellina, J. H., II; McMahon, J. B.; Buckheit, R. W., Jr.; Pannell, L. K.; Boyd, M. R. Plant Physiol. 1995, 108, 1353-1358.
42. (c) Gran, L. J. Am. Chem. Soc. 1994, 116, 9337-9338.
43. (a) Ganz, T.; Lehrer, R. I. Curr. Opin. Immunol. 1994, 6, 584-589.
44. (b) White, S. H.; Wimley, W. C.; Selsted, M. E. Curr. Opin. Struct. Biol. 1995, 5, 521-527.
45. (c) Ganz, T.; Lehrer, R. I. Curr. Opin. Immunol. 1998, 10, 41-44.
46. (d) Hancock, R. E.; Lehrer, R. I. Trends Biotechnol. 1998, 16, 82-88.
47. Gustafson, K. R.; Sowder, R. C., II; Henderson, L. E.; Parsons, I. C.; Kashman, Y.; Cardellina, J. H., II; McMahon, J. B.; Broekaert, W. F.; Terras, F. R.; Cammue, B. P.; Osborn, R. W. Plant Physiol. 1995, 108, 1353-1358.
48. (a) Lesieur, C.; Vecsey-Semjen, B.; Abraami, L.; Fivaz, M.; Gisou, van der Goot, F. Mol. Mem. Biol. 1997, 14, 45-64.
49. (b) Becerril, B.; Marangoni, S.; Possani, L. D. Toxicon 1997, 35, 821-835.
50. (a) Isaacs, N. W. Curr. Opinion Struct. Biol. 1995, 5, 391-395.
51. (b) Pallaghy, P. K.; Nielsen, K. J.; Craik, D. J.; Norton, R. S. Protein Sci. 1994, 3, 1833-1839.
52. (c) Narasimhan, L.; Singh, J.; Humblet, C.; Guruprasad, K.; Blundell, T. Nature Struct. Biol. 1994, 1, 850-852.
53. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
54. (b) Merrifield, R. B. Science 1986, 57, 1619-1625.
55. Hojo, H.; Aimoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 111-117.
56. Veber, D. F.; Milkowski, J. D.; Varga, S. L.; Denkewalter, R. G.; Hirschmann, R. J. Am. Chem. Soc. 1972, 94, 5456.
57. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648-2650.
58. (a) Tam, J. P.; Lu, Y.-A.; Liu, C.-F.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489.
59. (b) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
60. (a) Qu, X. D.; Harwig, S. S.; Shafer, W. M.; Lehrer, R. I. Infect. Immun. 1997, 65, 636-639.
61. (b) Yasin, B.; Lehrer, R. I.; Harwig, S. S.; Wagar, E. A. Infect. Immun. 1996, 64, 4863-4866.
62. (c) Saito, T.; Kawabata, S.; Shigenaga, T.; Takayenoki, Y.; Cho, J.; Nakajima, H.; Hirata, M.; Iwanaga, S. J. Biochem. 1995, 117, 1131-1137.
63. Sanger, F. Biochem. J. 1949, 45, 563-574.
64. Tam, J. P.; Wu, C.-R.; Liu, W.; Zhang, J.-W. J. Am. Chem. Soc. 1991, 113, 6657-6662.
65. Yang, Y.; Sweeney, W. V.; Schneider, K.; Chait, B. T.; Tam, J. P. Protein Sci. 1994, 3, 1267-1275.
66. (a) Liu, C. F.; Rao, C.; Tam, J. P. J. Am. Chem. Soc. 1996, 116, 4149-4153.
67. (b) Tam, J. P.; Yu, Q. Biopolymers 1998, 46, 319-327.
68. (a) Spetzler, J. C.; Tam, J. P. Int. J. Peptide Protein Res. 1995, 45, 78-85.
69. (b) Spetzler, J. C.; Tam, J. P. Peptide Res. 1996, 9, 290-296.
70. (c) Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893-3899.
71. (a) Muir, T. W.; Sondhi, D.; Cole, P. A. Proc. Natl. Acd. Sci. U.S.A. 1998, 95, 6705-6710.
72. (b) Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, B. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
73. (c) Hackeng, T. M.; Mounier, C. M.; Bon, C.; Dawson, P. E.; Griffin, J. H. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7845-7850.
74. (a) Zeng, F.; Zimmerman, S. C. J. Am. Chem. Soc. 1996, 118, 5326-5327.
75. (b) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073-12074.
76. Spetzler, J. C.; Tam, J. P. Int. J. Pept. Protein Res. 1995, 45, 78-85.
77. (b) Spetzler, J. C.; Tam, J. P. Peptide Res. 1996, 9, 290-296.
78. (c) Shao, J.; Tam, J. P. J. Am. Chem. Soc. 1995, 117, 3893-3899.
79. (a) Xu, M. Q.; Southworth, M. W.; Mersha, F. B.; Hornstra, L. J.; Perler, F. B. Cell 1993, 75, 1371-1377.
80. (b) Xu, M.-Q.; Comb, D. G.; Paulus, H.; Noren, C. J.; Shao, Y.; Perler, F. B. EMBO J. 1994, 13, 5517-5522.
81. Lehrer, R. I.; Rosenman, M.; Harwig, S. S. L.; Jackson, R.; Eisenhauer, P. J. Immunol. Methods 1991, 137, 167-173.