Unique α,β- and α,α,β,β-peptide foldamers based on cis-β-aminocyclopentanecarboxylic acid

Angewandte Chemie - International Edition

Volumn 51, Issue 9, 2012, Pages 2208-2212

  Berlicki, Łukasz ^a,b   Pilsl, Ludwig ^a   Wéber, Edit ^c   Mándity, István M ^c   Cabrele, Chiara ^d,e   Martinek, Tamás A ^c   Fülöp, Ferenc ^c   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF SZEGED   (Hungary)

^d RUHR UNIVERSITY BOCHUM   (Germany)

^e UNIVERSITY OF SALZBURG   (Austria)

Author keywords

amino acids; cis pentacine; foldamers; helical structures; peptides

Indexed keywords

AQUEOUS MEDIA; BUILDING BLOCKES; CIS-PENTACINE; FOLDAMERS; HELICAL STRUCTURES; HIGH STABILITY;

AMINO ACIDS; METHANOL;

PEPTIDES;

CYCLOLEUCINE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE;

CYCLOLEUCINE; MODELS, MOLECULAR; PEPTIDES; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY;

EID: 84857609735     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107702     Document Type: Article

References (56)

1. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180
2. A. D. Bautista, C. J. Craig, E. A. Harker, A. Schepartz, Curr. Opin. Chem. Biol. 2007, 11, 685-692
3. C. M. Goodman, S. Choi, S. Shandler, W. F. DeGrado, Nat. Chem. Biol. 2007, 3, 252-262.
4. Y. Hamuro, J. P. Schneider, W. F. DeGrado, J. Am. Chem. Soc. 1999, 121, 12200-12201
5. E. A. Porter, X. Wang, H.-S. Lee, B. Weisblum, S. H. Gellman, Nature 2000, 404, 565
6. D. Liu, W. F. DeGrado, J. Am. Chem. Soc. 2001, 123, 7553-7559
7. P. I. Arvidsson, J. Frackenpohl, N. S. Ryder, B. Liechty, F. Petersen, H. Zimmermann, G. P. Camenisch, R. Woessner, D. Seebach, ChemBioChem 2001, 2, 771-773
8. T. L. Raguse, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 12774-12785
9. M. A. Schmitt, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2004, 126, 6848-6849
10. R. F. Epand, L. Raguse, S. H. Gellman, R. M. Epand, Biochemistry 2004, 43, 9527-9535
11. E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 11516-11529
12. P. I. Arvidsson, N. S. Ryder, H. M. Weiss, D. F. Hook, J. Escalante, D. Seebach, Chem. Biodiversity 2005, 2, 401-420
13. R. F. Epand, M. A. Schmitt, S. H. Gellman, R. M. Epand, Biochim. Biophys. Acta Biomembr. 2006, 1758, 1343-1350
14. M. A. Schmitt, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 417-428
15. G. N. Tew, R. W. Scott, M. L. Klein, W. F. DeGrado, Acc. Chem. Res. 2010, 43, 30-39.
16. J. A. Kritzer, J. D. Lear, M. E. Hodsdon, A. Schepartz, J. Am. Chem. Soc. 2004, 126, 9468-9469
17. J. A. Kritzer, N. W. Luedtke, E. A. Harker, A. Schepartz, J. Am. Chem. Soc. 2005, 127, 14584-14585
18. J. D. Sadowsky, M. A. Schmitt, H.-S. Lee, N. Umezawa, S. Wang, Y. Tomita, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 11966-11968
19. J. D. Sadowsky, W. D. Fairlie, E. B. Hadley, H.-S. Lee, N. Umezawa, Z. Nikolovska-Coleska, S. Wang, D. C. S. Huang, Y. Tomita, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 139-154
20. E. F. Lee, J. D. Sadowsky, B. J. Smith, P. E. Czabotar, K. J. Peterson-Kaufman, P. M. Colman, S. H. Gellman, W. D. Fairlie, Angew. Chem. 2009, 121, 4382-4386
21. Angew. Chem. Int. Ed. 2009, 48, 4318-4322.
22. F. RAa, S. Boussert, T. Parella, I. Díez-Pérez, V. Branchadell, E. Giralt, R. M. Ortuño, Org. Lett. 2007, 9, 3643-3645
23. E. Torres, E. Gorrea, K. K. Burusco, E. Da-Silva, P. Nolis, F. RAa, S. Boussert, I. Díez-Pérez, S. Dannenberg, S. Izquierdo, E. Giralt, C. Jaime, V. Branchadell, R. M. Ortuño, Org. Biomol. Chem. 2010, 8, 564-575
24. E. Torres, J. Puigmarti-Luis, A. Perez-del-Pino, R. M. Ortuño, D. B. Amabilino, Org. Biomol. Chem. 2010, 8, 1661-1665.
25. D. Seebach, D. F. Hook, A. Glättli, Biopolymers 2006, 84, 23-37
26. D. H. Appella, L. A. Christianson, D. A. Klein, D. R. Powell, X. Huang, J. J. Barchi, S. H. Gellman, Nature 1997, 387, 381-384
27. P. I. Arvidsson, N. S. Ryder, H. M. Weiss, G. Gross, O. Kretz, R. Woessner, D. Seebach, ChemBioChem 2003, 4, 1345-1347
28. G. V. M. Sharma, P. Nagendar, P. Jayaprakash, P. Radha-Krishna, K. V. S. Ramakrishna, A. C. Kunwar, Angew. Chem. 2005, 117, 6028-6032
29. Angew. Chem. Int. Ed. 2005, 44, 5878-5882
30. G. Srinivasulu, S. K. Kumar, G. V. M. Sharma, A. C. Kunwar, J. Org. Chem. 2006, 71, 8395-8400.
31. R. P. Cheng, W. F. DeGrado, J. Am. Chem. Soc. 2001, 123, 5162-5163
32. P. I. Arvidsson, M. Rueping, D. Seebach, Chem. Commun. 2001, 649-650
33. S. A. Hart, A. B. F. Bahadoor, E. E. Matthews, X. J. Qiu, A. Schepartz, J. Am. Chem. Soc. 2003, 125, 4022-4023.
34. F. Fülöp, T. A. Martinek, G. K. Tõth, Chem. Soc. Rev. 2006, 35, 323-334.
35. L. Pilsl, O. Reiser, Amino Acids 2011, 41, 709-718. Examples
36. A. Hayen, M. A. Schmitt, F. N. Ngassa, K. A. Thomasson, S. H. Gellman, Angew. Chem. 2004, 116, 511-516
37. Angew. Chem. Int. Ed. 2004, 43, 505-510
38. S. De-Pol, C. Zorn, C. D. Klein, O. Zerbe, O. Reiser, Angew. Chem. 2004, 116, 517-520
39. Angew. Chem. Int. Ed. 2004, 43, 511-514.
40. I. M. Mándity, E. Wéber, T. A. Martinek, G. Olajos, G. K. Tõth, E. Vass, F. Fülöp, Angew. Chem. 2009, 121, 2205-2209
41. Angew. Chem. Int. Ed. 2009, 48, 2171-2175.
42. R. V. Jones, L. Godorhazy, N. Varga, D. Szalay, L. Urge, F. Darvas, J. Comb. Chem. 2005, 8, 110-116
43. I. M. Mándity, L. Fülöp, E. Vass, G. K. Tõth, T. A. Martinek, F. Fülöp, Org. Lett. 2010, 12, 5584-5587.
44. M. M. Juban, M. M. Javadpour, M. D. Barkley, Methods Mol. Biol. 1998, 78, 73-78
45. W. C. Johnson, Annu. Rev. Biophys. Chem. 1988, 17, 145-166.
46. D. H. Appella, J. J. Barchi,- Jr., S. R. Durell, S. H. Gellman, J. Am. Chem. Soc. 1999, 121, 2309-2310
47. X. Wang, J. F. Espinosa, S. H. Gellman, J. Am. Chem. Soc. 2000, 122, 4821-4822
48. H.-S. Lee, F. A. Syud, X. Wang, S. H. Gellman, J. Am. Chem. Soc. 2001, 123, 7721-7722
49. P. R. LePlae, J. D. Fisk, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 6820-6821
50. T. L. Raguse, J. R. Lai, S. H. Gellman, J. Am. Chem. Soc. 2003, 125, 5592-5593
51. M. A. Schmitt, S. H. Choi, I. A. Guzei, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 13130-13131
52. T. Sawada, S. H. Gellman, J. Am. Chem. Soc. 2011, 133, 7336-7339
53. M. Lee, T. L. Raguse, M. Schinnerl, W. C. Pomerantz, X. Wang, P. Wipf, S. H. Gellman, Org. Lett. 2007, 9, 1801-1804
54. E. Vaz, W. C. Pomerantz, M. Geyer, S. H. Gellman, L. Brunsveld, ChemBioChem 2008, 9, 2254-2259.
55. It has been concluded that the analysis of temperature coefficients for α-polypeptides in water cannot be used alone to infer the presence of internal hydrogen bonds; see:, N. H. Andersen, J. W. Neidigh, S. M. Harris, G. M. Lee, Z. Liu, H. Tong, J. Am. Chem. Soc. 1997, 119, 8547-8561. However, the broad range of T-values observed within each single peptide in this study supports the presence of amide groups with different properties. This has been further corroborated by the refined structures based on the combination of ROEs and molecular dynamics.
56. C. Baldauf, R. Günther, H.-J. Hofmann, Biopolymers 2006, 84, 408-413. In this study several conformers of 16/18 helices were predicted, which have alternating i, i-4 and i, i+5 C-HN interactions.