Consecutive cyclic pentapeptide modules form short α-helices that are very stable to water and denaturants

Angewandte Chemie - International Edition

Volumn 43, Issue 20, 2004, Pages 2687-2690

  Shepherd, Nicholas E ^a   Abbenante, Giovanni ^a   Fairlie, David P ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Helical structures; Helicity; Helix mimetics; Peptidomimetics

Indexed keywords

DENATURANTS; HELICES;

PROTEINS;

WATER;

GUANIDINE HYDROCHLORIDE; MACROCYCLIC COMPOUND; PENTAPEPTIDE; TRYPSIN; WATER;

ALPHA HELIX; AMINO ACID SEQUENCE; ARTICLE; PROTEIN CONFORMATION; PROTEIN DEGRADATION; PROTEIN DENATURATION; PROTEIN STABILITY;

AMINO ACID SEQUENCE; CIRCULAR DICHROISM; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PROTEIN DENATURATION; PROTEIN STRUCTURE, SECONDARY; SOLVENTS; WATER;

EID: 4544349166     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352659     Document Type: Article

References (47)

1. Reviews: a) D. P. Fairlie, M. West, A. Wong, Curr. Med. Chem. 1998, 5, 29;
2. b) M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711.
3. a) B. Zimm, J. Bragg, J. Chem. Phys. 1959, 31, 526;
4. b) A. Scholtz, R. L. Baldwin, Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 95.
5. a) D. Kemp, T. Curran, J. Boyd, T. J. Allen, J. Org. Chem. 1991, 56, 6683;
6. b) K. Müller, D. Obrecht, A. Knierzinger, C. Stankovic, C. Spiegler, W. Bannwarth, A. Trzeciak, G. Englert, A. M. Labhardt, P. Schoenholzer, Perspect. Med. Chem. 1993, 513;
7. c) R. Austin, R. A. Maplestone, A. M. Sefler, K. Liu, W. N. Hruzewicz, C. Liu, H. S. Cho, D. E. Wemmer, P. A. Bartlett, J. Am. Chem. Soc. 1997, 119, 6461;
8. d) R. Aurora, G. D. Rose, Protein Sci. 1998, 7, 21.
9. a) M. R. Ghadiri, C. Choi, J. Am. Chem. Soc. 1990, 112, 1630;
10. b) F. Ruan, Y. Chen, P. B. Hopkins, J. Am. Chem. Soc. 1990, 112, 9403;
11. c) M. R. Ghadiri, H. Fernholz, J. Am. Chem. Soc. 1990, 112, 9633;
12. d) W. D. Kohn, C. M. Kay, B. D. Sykes, R. S. Hodges, J. Am. Chem. Soc. 1998, 120, 1124;
13. e) M. J. Kelso, H. Hoang, T. G. Appleton, D. P. Fairlie, J. Am. Chem. Soc. 2000, 122, 10488.
14. a) K. R. Rajashankar, S. Ramakumar, R. M. Jain, V. S. Chauhan, J. Am. Chem. Soc. 1995, 117, 10129;
15. b) I. L. Karle, P. Balaram, Biochemistry 1990, 29, 6747.
16. a) L. Mayne, S. W. Englander, R. Qiu, J. Yang, Y. Gong, E. J. Spek, N. R. Kallenbach, J. Am. Chem. Soc. 1998, 120, 10643;
17. b) J. S. Albert, A. Hamilton, Biochemistry 1995, 34, 984.
18. a) M. Pellegrini, M. Royo, M. Chorev, D. F. Mierke, J. Pept. Res. 1997, 49, 404;
19. b) D. Y. Jackson, D. S. King, J. Chmielewski, S. Singh, P. G. Schultz, J. Am. Chem. Soc. 1991, 113, 9391.
20. E. Cabezas, A. C. Satterthwait, J. Am. Chem. Soc. 1999, 121, 3862.
21. a) J. W. Taylor, Biopolymers 2002, 66, 49;
22. b) E. Schievano, S. Mammi, A. Bisello, M. Rosenblatt, M. Chorev, E. Peggion, J. Pept. Sci. 1999, 5, 330;
23. c) C. Bracken, J. Gulyas, J. W. Taylor, J. Baum, J. Am. Chem. Soc. 1994, 116, 6431;
24. d) J. C. Phelan, N. J. Skelton, A. C. Braisted, R. S. McDowell, J. Am. Chem. Soc. 1997, 119, 455;
25. e) J. W. Taylor, C. Yu, Bioorg. Med. Chem. 1999, 7, 161;
26. f) S. T. Chen, H. J. Chen, H. M. Yu, K. T. J. Wang, J. Chem. Res. Synop. 1993, 228;
27. g) G. Osapay, J. W. Taylor, J. Am. Chem. Soc. 1992, 114, 6966;
28. h) C. Yu, J. W. Taylor, Tetrahedron Lett. 1996, 37, 1731;
29. i) T. R. Geistlinger, R. K. Guy, J. Am. Chem. Soc. 2001, 123, 1525.
30. a) C. E. Schafmeister, J. Po, G. L. Verdine, J. Am. Chem. Soc. 2000, 122, 5891;
31. b) H. E. Blackwell, J. D. Sadowsky, R. J. Howard, J. N. Sampson, J. A. Chao, W. E. Steinmetz, D. J. O'Leary, R. H. Grubbs, J. Org. Chem. 2001, 66, 5291;
32. c) J. K. Judice, J. Y. K. Tom, W. Huang, T. Wrin, J. Vennari, C. J. Petropoulos, R. S. McDowell, Proc. Natl. Acad. Sci. USA 1997, 94, 13426.
33. a) B. P. Orner, J. T. Ernst, A. D. Hamilton, J. Am. Chem. Soc. 2001, 123, 5382;
34. b) O. Kutzki, H. S. Park, J. T. Ernst, B. P. Orner, H. Yin, A. D. Hamilton, J. Am. Chem. Soc. 2002, 124, 11838
35. c) J. T. Ernst, J. Becerril, H. S. Park, H. Yin, A. D. Hamilton, Angew. Chem. 2003, 115, 553; Angew. Chem. Int. Ed. 2003, 42, 535.
36. c) J. T. Ernst, J. Becerril, H. S. Park, H. Yin, A. D. Hamilton, Angew. Chem. 2003, 115, 553; Angew. Chem. Int. Ed. 2003, 42, 535.
37. -1 (P. Luo, R. L. Baldwin, Biochemistry 1997, 36, 8413) and k = 2.6 (Y. H. Chen, Biochemistry 1974, 13, 3350).
38. 0192 did not change when the concentration was halved, doubled, or quadrupled, which indicates that the peptides were monomeric (see the Supporting Information).
39. a) P. Wallimann, R. J. Kennedy, J. S. Miller, W. Shalongo, D. S. Kemp, J. Am. Chem. Soc. 2003, 125, 1203;
40. b) "Synthesis of Peptides and Peptidomimetics": R. W. Woody in Methods of Org. Chem., Vol. E22 (Houben-Weyl), 4th ed. 1995;
41. c) J. R. Lawrence, W. C. Johnson, Biophys. Chem. 2002, 101-102, 375.
42. H. J. Dyson, P. E. Wright, Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519.
43. J. P. Waltho, V. A. Feher, G. Merutka, H. J. Dyson, P. E. Wright, Biochemistry 1993, 32, 6337.
44. K. Wüthrich, M. Billeter, W. Braun, J. Mol. Biol. 1984, 180, 715.
45. αN(i, i + 4) NOE interactions in this region, for clarity ambiguous NOE interactions were omitted from structural calculations.
46. P. Güntert, C. Mumenthaler, K. Wüthrich, J. Mol. Biol. 1997, 273, 283.
47. A. T. Brünger, X-PLOR Manual Version 3.1, 1992, Yale University, New Haven, CT.