Efficient α-helix induction in a linear peptide chain by n-capping with a bridged-tricyclic diproline analogue

Angewandte Chemie - International Edition

Volumn 52, Issue 36, 2013, Pages 9539-9543

  Hack, Verena ^a   Reuter, Cédric ^a   Opitz, Robert ^b   Schmieder, Peter ^b   Beyermann, Michael ^b   Neudörfl, Jörg Martin ^a   Kühne, Ronald ^b   Schmalz, Hans Günther ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

^b LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

Author keywords

conformational analysis; molecular modeling; peptides and peptide mimics; protein protein interactions; ring closing metathesis

Indexed keywords

CONFORMATIONAL ANALYSIS; HELIX FORMATION; PEPTIDE MIMICS; PROTEIN INTERACTION; PROTEIN-PROTEIN INTERACTIONS; RING CLOSING METATHESIS; SECONDARY STRUCTURES; STEREO-SELECTIVE;

AMINO ACIDS; MOLECULAR MODELING;

PEPTIDES;

PEPTIDE; PROLINE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATIONAL ANALYSIS; CYCLIZATION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES AND PEPTIDE MIMICS; PROTEIN SECONDARY STRUCTURE; PROTEIN-PROTEIN INTERACTIONS; RING-CLOSING METATHESIS; X RAY CRYSTALLOGRAPHY;

CONFORMATIONAL ANALYSIS; MOLECULAR MODELING; PEPTIDES AND PEPTIDE MIMICS; PROTEIN-PROTEIN INTERACTIONS; RING-CLOSING METATHESIS;

AMINO ACID SEQUENCE; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PEPTIDES; PROLINE; PROTEIN STRUCTURE, SECONDARY;

EID: 84883238732     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302014     Document Type: Article

References (54)

1. H. Jubb, A. P. Higueruelo, A. Winter, T. L. Blundell, Trends Pharmacol. Sci. 2012, 33, 241-248
2. V. Azzarito, K. Long, N. S. Murphy, A. J. Wilson, Nat. Chem. 2013, 5, 161-173
3. S. Asada, Y. Choi, M. Uesugi, J. Am. Chem. Soc. 2003, 125, 4992-4993.
4. A. Shaginian, L. R. Whitby, S. Hong, I. Hwang, B. Farooqi, M. Searcey, J. Chen, P. K. Vogt, D. L. Boger, J. Am. Chem. Soc. 2009, 131, 5564-5572
5. L. R. Whitby, K. E. Boyle, L. Cai, X. Yu, M. Gochin, D. L. Boger, Bioorg. Med. Chem. Lett. 2012, 22, 2861-2865
6. L. R. Whitby, D. L. Boger, Acc. Chem. Res. 2012, 45, 1698-1709.
7. J. A. Hebda, I. Saraogi, M. Magzoub, A. D. Hamilton, A. D. Miranker, Chem. Biol. 2009, 16, 943-950
8. G. C. Cummings, A. D. Hamilton, Curr. Opin. Chem. Biol. 2010, 14, 341-346.
9. J. A. Wells, C. L. McClendon, Nature 2007, 450, 1001-1009
10. L. Jochim, P. S. Arora, ACS Chem. Biol. 2010, 5, 919-923.
11. Y. Che, B. R. Brooks, G. R. Marshall, Biopolymers 2007, 86, 288-297.
12. R. J. Simon, R. S. Kania, R. N. Zuckermann, V. D. Huebner, D. A. Jewell, S. Banville, S. Ng, L. Wang, S. Rosenberg, C. K. Marlowe, Proc. Natl. Acad. Sci. USA 1992, 89, 9367-9371.
13. T. Kimmerlin, R. Sebesta, A. M. Campo, A. K. Beck, D. Seebach, Tetrahedron 2004, 60, 7455-7506.
14. H. Yin, A. D. Hamilton, Angew. Chem. 2005, 117, 4200-4235
15. Angew. Chem. Int. Ed. 2005, 44, 4130-4163
16. H. Yin, G. I. Lee, K. A. Sedey, J. M. Rodriguez, H. G. Wang, S. M. Sebti, A. D. Hamilton, J. Am. Chem. Soc. 2005, 127, 5463-5468; see also
17. C. P. Gomes, A. Metz, J. W. Bats, H. Gohlke, M. W. Göbel, Eur. J. Org. Chem. 2012, 3270-3277; and references cited therein.
18. D. S. Kemp, J. G. Boyd, C. C. Muendel, Nature 1991, 352, 451-454; see also
19. D. S. Kemp, J. G. Boyd, C. C. Muendel, J. Am. Chem. Soc. 2006, 128, 7917-7928.
20. B. Heitmann, G. E. Job, R. J. Kennedy, S. M. Walker, D. S. Kemp, J. Am. Chem. Soc. 2005, 127, 1690-1704.
21. J. Zaminer, C. Brockmann, P. Huy, R. Opitz, C. Reuter, M. Beyermann, C. Freund, M. Müller, H. Oschkinat, R. Kühne, H.-G. Schmalz, Angew. Chem. 2010, 122, 7265-7269
22. C. Reuter, P. Huy, J.-M. Neudörfl, R. Kühne, H.-G. Schmalz, Chem. Eur. J. 2011, 17, 12037-12044.
23. K. S. Lee, J. H. Lim, Y. K. Kang, K. H. Yoo, D. C. Kim, K. J. Shin, D. J. Kim, Eur. J. Med. Chem. 2006, 41, 495-503
24. T. Honda, R. Takahashi, H. Namiki, J. Org. Chem. 2005, 70, 499-504
25. K. K. Schumacher, J. Jiang, M. M. Joullie, Tetrahedron: Asymmetry 1998, 9, 47-54.
26. K. Hamacher, J. Labelled Compd. Radiopharm. 1999, 42, 1135-1144
27. R. Caputo, M. Dellagreca, I. De Paola, L. Longobardo, D. Mastroianni, Amino Acids 2010, 38, 305-310.
28. R. J. Bridges, M. S. Stanley, M. W. Anderson, C. W. Cotman, A. R. Chamberlin, J. Med. Chem. 1991, 34, 717-725.
29. S. Scapecchi, R. Matucci, C. Bellucci, M. Buccioni, S. Dei, L. Guandalini, C. Martelli, D. Manetti, E. Martini, G. Marucci, M. Nesi, M. N. Romanelli, E. Teodori, F. Gualtieri, J. Med. Chem. 2006, 49, 1925-1931.
30. J. B. Epp, T. S. Widlanski, J. Org. Chem. 1999, 64, 293-295.
31. P. Huy, H.-G. Schmalz, Synthesis 2011, 954-960.
32. K. F. McClure, P. Renold, D. S. Kemp, J. Org. Chem. 1995, 60, 454-457.
33. F. Nagaike, Y. Onuma, C. Kanazawa, H. Hojo, A. Ueki, Y. Nakahara, Y. Nakahara, Org. Lett. 2006, 8, 4465-4468.
34. A. El-Faham, R. Subirõs Funosas, R. Prohens, F. Albericio, Chem. Eur. J. 2009, 15, 9404-9416.
35. I. Coin, M. Beyermann, M. Bienert, Nat. Protoc. 2007, 2, 3247-3256.
36. M. Beyermann, S. Rothemund, N. Heinrich, K. Fechner, J. Furkert, M. Dathe, R. Winter, E. Krause, M. Bienert, J. Biol. Chem. 2000, 275, 5702-5709.
37. J. Reed, T. A. Reed, Anal. Biochem. 1997, 254, 36-40.
38. N. Sreerama, S. Y. Venyaminov, R. Woody, Anal. Biochem. 2000, 287, 243-251.
39. G. Böhm, R. Muhr, R. Jaenicke, Protein Eng. 1992, 5, 191-191.
40. N. J. Greenfield, Nat. Protoc. 2007, 1, 2876-2890.
41. M. L. Tiffany, S. Krimm, Biopolymers 1969, 8, 347-359.
42. C. Toniolo, A. Polese, F. Formaggio, M. Crisma, J. Kamphuis, J. Am. Chem. Soc. 1996, 118, 2744-2745
43. Z. Biron, S. Khare, A. O. Samson, Y. Hayek, F. Naider, J. Anglister, Biochemistry 2002, 41, 12687-12696.
44. L. A. Compton, W. C. Johnson, Anal. Biochem. 1986, 155, 155-167.
45. G. Holzwarth, P. Doty, J. Am. Chem. Soc. 1965, 87, 218-228.
46. J. Cavanagh, M. Rance, J. Magn. Reson. 1992, 96, 670-678
47. A. Bax, D. G. Davis, J. Magn. Reson. 1985, 65, 355-360.
48. P. Schanda, E. Kupce, B. Brutscher, J. Biomol. NMR 2005, 33, 199-211.
49. D. S. Wishart, B. D. Skyes, Methods Enzymol. 1994, 239, 363-392.
50. A. A. Bothner-By, R. L. Stephens, J. Lee, C. D. Warren, R. W. Jeanloz, J. Am. Chem. Soc. 1984, 106, 811-813
51. H. Kessler, C. Griesinger, R. Kerssebaum, K. Wagner, R. R. Ernst, J. Am. Chem. Soc. 1987, 109, 607-609.
52. B. Forood, E. J. Feliciano, K. P. Nambiar, Proc. Natl. Acad. Sci. USA 1993, 90, 838-842.
53. M. L. Tiffany, S. Krimm, Biopolymers 1973, 12, 575-587.
54. CCDC 932373 (12) and CCDC 932374 (17) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.