Mixed oligoureas based on constrained bicyclic and acyclic β-amino acids derivatives: On the significance of the subunit configuration for folding

Chemistry - A European Journal

Volumn 19, Issue 50, 2013, Pages 16963-16971

  André, Christophe ^a   Legrand, Baptiste ^a   Moulat, Laure ^a   Wenger, Emmanuel ^b   Didierjean, Claude ^b   Aubert, Emmanuel ^b   Averlant Petit, Marie Christine ^b   Martinez, Jean ^a   Amblard, Muriel ^a   Calmes, Monique ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

Author keywords

bicyclic amino acid derivatives; conformation analysis; foldamers; helical structures; mixed oligoureas

Indexed keywords

AMINO ACIDS; DICHROISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; UREA;

AMINO ACID DERIVATIVES; CONFORMATION ANALYSIS; FOLDAMERS; HELICAL STRUCTURES; OLIGOUREAS;

CRYSTAL STRUCTURE;

AMINO ACID; BICYCLO COMPOUND; BICYCLOOCTANE; DRUG DERIVATIVE; OCTANE; UREA;

ARTICLE; BICYCLIC Β-AMINO ACID DERIVATIVES; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; CONFORMATION ANALYSIS; FOLDAMERS; HELICAL STRUCTURES; MIXED OLIGOUREAS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SECONDARY STRUCTURE; SOLUTION AND SOLUBILITY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

BICYCLIC Β-AMINO ACID DERIVATIVES; CONFORMATION ANALYSIS; FOLDAMERS; HELICAL STRUCTURES; MIXED OLIGOUREAS;

AMINO ACIDS; BICYCLO COMPOUNDS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OCTANES; PROTEIN STRUCTURE, SECONDARY; SOLUTIONS; STEREOISOMERISM; UREA;

EID: 84889587181     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302829     Document Type: Article

References (53)

1. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180
2. S. Hanessian, X. H. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569-8570
3. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011
4. R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232
5. C. M. Goodman, S. Choi, S. Shandler, W. F. DeGrado, Nat. Chem. Biol. 2007, 3, 252-262
6. F. Bouillère, S. Thetiot-Laurent, C. Kouklovsky, V. Alezra, Amino Acids 2011, 41, 687-707
7. T. A. Martinek, F. Fulop, Chem. Soc. Rev. 2012, 41, 687-702.
8. D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodiversity 2004, 1, 1111-1239.
9. S. De Pol, C. Zorn, C. D. Klein, O. Zerbe, O. Reiser, Angew. Chem. 2004, 116, 517-520
10. Angew. Chem. Int. Ed. 2004, 43, 511-514
11. A. Hayen, M. A. Schmitt, F. N. Ngassa, K. A. Thomasson, S. H. Gellman, Angew. Chem. 2004, 116, 511-516
12. Angew. Chem. Int. Ed. 2004, 43, 505-510
13. G. V. M. Sharma, P. Nagendar, P. Jayaprakash, P. R. Krishna, K. V. S. Ramakrishna, A. C. Kunwar, Angew. Chem. 2005, 117, 6028-6032
14. Angew. Chem. Int. Ed. 2005, 44, 5878-5882
15. G. Srinivasulu, S. K. Kumar, G. V. M. Sharma, A. C. Kunwar, J. Org. Chem. 2006, 71, 8395-8400
16. D. Seebach, B. Jaun, R. Sebesta, R. I. Mathad, O. Flogel, M. Limbach, H. Sellner, S. Cottens, Helv. Chim. Acta 2006, 89, 1801-1825
17. W. S. Horne, S. H. Gellman, Acc. Chem. Res. 2008, 41, 1399-1408
18. P. G. Vasudev, S. Chatterjee, N. Shamala, P. Balaram, Chem. Rev. 2011, 111, 657-687
19. L. K. A. Pilsl, O. Reiser, Amino Acids 2011, 41, 709-718
20. T. A. Martinek, I. M. Mándity, L. Fulop, G. K. Toth, E. Vass, M. Hollosi, E. Forro, F. Fulop, J. Am. Chem. Soc. 2006, 128, 13539-13544
21. I. M. Mándity, E. Weber, T. A. Martinek, G. Olajos, G. K. Toth, E. Vass, F. Fulop, Angew. Chem. 2009, 121, 2205-2209
22. Angew. Chem. Int. Ed. 2009, 48, 2171-2175
23. I. M. Mándity, L. Fulop, E. Vass, G. K. Toth, T. A. Martinek, F. Fulop, Org. Lett. 2010, 12, 5584-5587.
24. V. Semetey, D. Rognan, C. Hemmerlin, R. Graff, J. P. Briand, M. Marraud, G. Guichard, Angew. Chem. 2002, 114, 1973-1975
25. Angew. Chem. Int. Ed. 2002, 41, 1893-1895.
26. A. Violette, M. C. Averlant-Petit, V. Semetey, C. Hemmerlin, R. Casimir, R. Graff, M. Marraud, J. P. Briand, D. Rognan, G. Guichard, J. Am. Chem. Soc. 2005, 127, 2156-2164.
27. L. Fischer, P. Claudon, N. Pendem, E. Miclet, C. Didierjean, E. Ennifar, G. Guichard, Angew. Chem. 2010, 122, 1085-1088
28. Angew. Chem. Int. Ed. 2009, 49, 1067-1070.
29. L. Fischer, G. Guichard, Org. Biomol. Chem. 2010, 8, 3101-3117.
30. J. Fremaux, L. Fischer, T. Arbogast, B. Kauffmann, G. Guichard, Angew. Chem. 2011, 123, 11584-11587
31. Angew. Chem. Int. Ed. 2011, 50, 11382-11385.
32. C. André, B. Legrand, C. Deng, C. Didierjean, G. Pickaert, J. Martinez, M. C. Averlant-Petit, M. Amblard, M. Calmes, Org. Lett. 2012, 14, 960-963.
33. B. Legrand, C. André, E. Wenger, C. Didierjean, M. Averlant-Petit, J. Martinez, M. Calmès, M. Amblard, Angew. Chem. Int. Ed. 2012, 51, 11267-11270.
34. For a recent review, see:, V. Azzarito, K. Long, N. S. Murphy, A. J. Wilson, Nat. Chem. 2013, 5, 161-173.
35. V. Semetey, C. Hemmerlin, C. Didierjean, A. P. Schaffner, A. G. Giner, A. Aubry, J. P. Briand, M. Marraud, G. Guichard, Org. Lett. 2001, 3, 3843-3846.
36. D. A. Case, T. A. Darden, T. E. Cheatham III, C. L. Simmerling, J. Wang, R. E. Duke, R. Luo, M. Crowley, R. C. Walker, W. Zhang, K. M. Merz, B. Wang, S. Hayik, A. Roitberg, G. Seabra, I. Kolossváry, K. F. Wong, Paesani. F., J. Vanicek, X. Wu, S. R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, D. H. Mathews, M. G. Seetin, C. Sagui, V. Babin, P. A. Kollman, AMBER 10, University of California, San Francisco. 2008
37. V. Hornak, R. Abel, A. Okur, B. Strockbine, A. Roitberg, C. Simmerling, Proteins Struct. Funct. Bioinf. 2006, 65, 712-725.
38. M. E. Brezgunova, E. Aubert, S. Dahaoui, P. Fertey, S. Lebegue, C. Jelsch, J. G. Angyan, E. Espinosa, Cryst. Growth Des. 2012, 12, 5373-5386.
39. N. Pendem, C. Douat, P. Claudon, M. Laguerre, S. Castano, B. Desbat, D. Cavagnat, E. Ennifar, B. Kauffmann, G. Guichard, J. Am. Chem. Soc. 2013, 135, 4884-4892.
40. O. Songis, C. Didierjean, C. Laurent, J. Martinez, M. Calmes, Eur. J. Org. Chem. 2007, 3166-3172.
41. G. Guichard, V. Semetey, C. Didierjean, A. Aubry, J. P. Briand, M. Rodriguez, J. Org. Chem. 1999, 64, 8702-8705.
42. I. Bertini, D. A. Case, L. Ferella, A. Giachetti, A. Rosato, Bioinformatics 2011, 27, 2384-2390.
43. B. A. Johnson, R. A. Blevins, J. Biomol. NMR 1994, 4, 603-614.
44. Wüthrich, K. NMR of Proteins and Nucleic acids, Wiley-Interscience: New York, 1986.
45. D. A. Case, T. A. Darden, T. E. Cheatham, III, C. L. Simmerling, J. Wang, R. E. Duke, R. Luo, M. Crowley, R. C. Walker, W. Zhang, K. M. Merz, B. Wang, S. Hayik, A. Roitberg, G. Seabra, I. Kolossváry, K. F. Wong, F. Paesani, J. Vanicek, X. Wu, S. R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, D. H. Mathews, M. G. Seetin, C. Sagui, V. Babin, and P. A. Kollman, AMBER 10, University of California, San Francisco 2008.
46. R. Koradi, M. Billeter, K. Wuthrich, J. Mol. Graph. 1996, 14, 51-54.
47. C. E. Dempsey, J. Am. Chem. Soc. 1995, 117, 7526-7534.
48. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381-388.
49. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
50. Gaussian 09. Revision C.01, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E., Robb, M.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J. and Fox, D. J.: Gaussian, Inc., Wallingford CT, 2010.
51. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
52. AIMAll software, T. A. Keith, TK Gristmill Software, Overland Park KS, USA, 2012 (aim.tkgristmill.com), AIMAll (Version 12.06.03).
53. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170-173.