Synthesis of a cyclic peptide containing norlanthionine: Effect of the thioether bridge on peptide conformation

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 8193-8198

  Mohd Mustapa, M Firouz ^a   Harris, Richard ^a   Esposito, Diego ^a   Chubb, Nathan A L ^b   Mould, Jessica ^b   Schultz, Darren ^b   Driscoll, Paul C ^a,c   Tabor, Alethea B ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c LUDWIG INSTITUTE FOR CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; ETHERS; ISOMERS; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

STEREOISOMERS;

LANTHANUM COMPOUNDS;

CYCLOPEPTIDE; LANTHIONINE; LANTIBIOTIC; NORLANTHIONINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; SYNTHESIS;

ALANINE; BRIDGED COMPOUNDS; MOLECULAR STRUCTURE; NISIN; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; STEREOISOMERISM; SULFIDES;

EID: 0142026525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0346407     Document Type: Article

References (60)

1. For recent reviews, see: (a) Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. J. Chem. Soc., Perkin Trans. 1 2001, 471.
2. (b) Tabor, A. B. Synthetic Pathways to Naturally Occurring Cyclic Peptides. In The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000.
3. (c) Blackburn, C.; Kates, S. A. Solid-Phase Synthesis of Cyclic Homodetic Peptides. In Methods in Enzymology, Vol. 289: Solid-Phase Peptide Synthesis; Fields, G. B., Ed.; Academic Press: New York, 1997; p 175.
4. (d) Fairlie, D. P.; Abbenante, G.; March, D. R. Curr. Med. Chem. 1995, 2, 654.
5. (e) Kates, S. A.; Solé, N. A.; Alberico, F.; Barany, G. Solid-Phase Synthesis of Cyclic Peptides. In Peptides: Design, Synthesis and Biological Activity; Basava, C., Anantharamaiah, G. M., Eds.; Birkhauser: Boston, 1994; p 39.
6. Recent examples and reviews: (a) Boger, D. L. Med. Res. Rev. 2001, 21, 356.
7. (b) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
8. (c) Boger, D. L.; Kim, S. H.; Mori, Y.; Weng, J. H.; Rogel, O.; Castle, S. L.; McAtee, J. J. J. Am. Chem. Soc. 2001, 123, 1862.
9. (d) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Yue, T. Y.; Natarajan, S.; Chu, X. J.; Brase, S.; Rubsam, F. Chem. Eur. J. 1999, 5, 2584.
10. (e) Nicolaou, K. C.; Boddy, C. N. C.; Li, H.; Koumbis, A. E.; Hughes, R. ; Natarajan, S.; Jain, N. F.; Ramanjulu, J. M.; Brase, S.; Solomon, M. E. Chem. Eur. J. 1999, 5, 2602.
11. (f) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2700.
12. (g) Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2704.
13. For recent reviews, see: (a) Li, P.; Roller, P. P.; Xu, J. C. Curr. Org. Chem. 2002, 6, 411.
14. (b) Venkatrama, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131.
15. (c) Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479.
16. For recent reviews, see: (a) Jung, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1051.
17. (b) Sahl, H.-G.; Jack, R. W.; Bierbaum, G. Eur. J. Biochem. 1995, 230, 827.
18. (c) Sahl, H.-G.; Bierbaum, G. Annu. Rev. Microbiol. 1998, 52, 41.
19. (d) van Kraaij, C.; de Vos, W. M.; Siezen, R. J.; Kuipers, O. P. Nat. Prod. Rep. 1999, 16, 575.
20. (e) Breukink, E.; de Kruijff, B. Biochim. Biophys. Acta 1999, 1462, 223.
21. (f) Guder, A.; Wiedemann, I.; Sahl, H.-G. Biopolymers 2000, 55, 62.
22. (g) Chem. Br. March 2000, 16.
23. (h) Bower, C. K.; Bothwell, M. K.; McGuire, J. Coll Surf B: Biointerfaces 2001, 22, 259.
24. (a) Ösapay, G.; Prokai, L.; Kim, H.-S.; Medzihradszky, K. F.; Coy, D. H.; Liapakis, G.; Reisine, T.; Melacini, G.; Zhu, Q.; Wang, S. H.-H.; Mattern, R.-H.; Goodman, M. J. Med. Chem. 1997, 40, 2241.
25. (b) Melacini, G.; Zhu, Q.; Ösapay, G.; Goodman, M. J. Med. Chem. 1997, 40, 2252.
26. (c) Polinsky, A.; Cooney, M. G.; Toy-Palmer, A.; Ösapay, G.; Goodman, M. J. Med. Chem. 1992, 35, 4185.
27. (d) Ösapay, G.; Goodman, M. J. Chem. Soc., Chem. Commun. 1993, 1599.
28. Yu, L.; Lai, Y.; Wade, J. V.; Coutts, S. M. Tetrahedron Lett. 1998, 39, 6633.
29. Feng, Y.; Pattarawarapan, M.; Wang, Z.; Burgess, K. Org. Lett. 1999, 1, 121.
30. Fukase, K.; Kitazawa, M.; Sano, A.; Shimbo, K.; Horimoto, S.; Fujita, H. ; Kubo, A.; Wakamiya, T.; Shiba, T. Bull. Soc. Chem. Jpn. 1992, 65, 2227.
31. Galande, A. K.; Spatola, A. F. Lett. Pept. Sci. 2001, 8, 247.
32. Mayer, J. P.; Zhang, J.; Groeger, S.; Liu, C.-F.; Jarosinski, M. A. J. Pept. Res. 1998, 51, 432.
33. Burrage, S.; Raynham, T.; Williams, G.; Essex, J. W.; Allen, C.; Cardno, M.; Swali, V.; Bradley, M. Chem. Eur. J. 2000, 6, 1455.
34. Zhou, H.; van der Donk, W. A. Org. Lett. 2002, 4, 1335.
35. (a) Hsu, S. T.; Breukink, E.; de Kruijff, B.; Kaptein, R.; Bonvin, A. M. J. J.; van Nuland, N. A. J. Biochemistry 2002, 41, 7670.
36. (b) Bonev, B. B.; Chan, W. C.; Bycroft, B. W.; Roberts, G. C.; Watts, A. Biochemistry 2000, 39, 11425.
37. (c) Schneider, T. R.; Karcher, J.; Pohl, E.; Lubini, P.; Sheldrick, G. M. Acta Crystallogr. D: Biol. Cryst. 2000, 56, 705.
38. (d) Turner, D. L.; Brennan, L.; Meyer, H. E.; Lohaus, C.; Siethoff, C.; Costa, H. C.; Gonzalez, B.; Santos, H.; Suárez, J. E. Eur. J. Biochem. 1999, 264, 833.
39. (e) Prasch, T.; Naumann, T.; Market, R. L. M.; Sattler, M.; Schubert, W. ; Schaal, S.; Bauch, M.; Kogler, H.; Griesinger, C. Eur. J. Biochem. 1997, 244, 501.
40. (f) van den Hooven, H. W.; Doeland, C. C.; van der Kamp, M.; Konings, R. N.; Hilbers, C. W.; van der Ven, F. J. Eur. J. Biochem. 1996, 235, 382.
41. (g) van der Ven, F. J.; van den Hooven, H. W.; Konings, R. N.; Hilbers, C. W. Eur. J. Biochem. 1991, 202, 1181.
42. (h) For a recent review of preceding work, see: van De Ven, F. J. M.; Jung, G. Antonie van Leeuwenhoek 1996, 69, 99.
43. Mohd Mustapa, M. F.; Harris, R.; Bulic-Subanovic, N.; Elliott, S. L.; Bregant, S.; Groussier, M. F. A.; Mould, J.; Chubb, N. A. L.; Schultz, D.; Gaffney, P. R. J.; Driscoll, P. C.; Tabor, A. B. J. Org. Chem. 2003, 68, 8185.
44. Alexander McNamara, L. M.; Andrews, M. J. I.; Mitzel, F.; Siligardi, G.; Tabor, A. B. J. Org. Chem. 2001, 66, 4585.
45. For preliminary results reporting the synthesis of the cyclic peptide, see: Mohd Mustapa, M. F.; Harris, R.; Mould, J.; Chubb, N. A. L.; Schultz, D.; Driscoll, P. C.; Tabor, A. B. Tetrahedron Lett. 2002, 43, 8363.
46. Fmoc Solid-Phase Synthesis: A Practical Approach; Chang, W., White, P., Eds.; OUP: Oxford, 1999.
47. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G. ; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552; Kates, S. A.; Daniels, S. B.; Albericio, F. Anal. Biochem. 1993, 212, 303.
48. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G. ; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552; Kates, S. A.; Daniels, S. B.; Albericio, F. Anal. Biochem. 1993, 212, 303.
49. Kaiser, E. T.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 84, 595.
50. McMurray J. S.; Lewis, C. A.; Obeyesekere, N. U. Pept. Res. 1994, 7, 195.
51. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355.
52. Bodenhausen, G.; Ruben, D. J. Chem. Phys. Lett. 1980, 69, 185.
53. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093.
54. Piotto, M.; Saudek, V.; Sklenar, V. J. Biomol. NMR 1992, 2, 661.
55. Delaglio, F.; Grzesiek, S.; Vuister, G. W.; Zhu, G.; Pfiefer, J.; Bax, A. J. Biomol. NMR 1995, 6, 277.
56. Kraulis, P. J. J. Magn. Reson. 1989, 24, 627.
57. Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
58. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811.
59. Brünger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gro, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr. 1998, 54, 905.
60. Linge, J. P.; Nilges, M. J. Biomol. NMR 1999, 13, 51.