Refoldable foldamers: Global conformational switching by deletion or insertion of a single hydrogen bond

Angewandte Chemie - International Edition

Volumn 55, Issue 6, 2016, Pages 2132-2136

  LeBailly, Bryden A F ^a   Byrne, Liam ^b   Clayden, Jonathan ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

biocatalysis; conformation; foldamers; peptides; photoswitches

Indexed keywords

CONFORMATIONS; HYDROGEN BONDS; PEPTIDES;

ASYMMETRIC INDUCTION; BIOCATALYSIS; CATALYTIC SITES; CONFORMATIONAL PREFERENCES; CONFORMATIONAL SWITCHING; DEPROTECTION; FOLDAMERS; PHOTOSWITCHES;

AMPHIPHILES;

EID: 84954457417     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201510605     Document Type: Article

References (61)

1. A. Fersht, Enzyme Structure and Mechanism, W.H. Freeman, New York, 1985.
2. L. T. J. Delbaere, W. L. B. Hutcheon, M. N. G. James, W. E. Thiessen, Nature 1975, 257, 758-763.
3. P. W. J. Rigby, B. D. Burleigh, B. S. Hartley, Nature 1974, 251, 200-204.
4. J.-C. Micheau, J. Zhao, J. Phys. Org. Chem. 2007, 20, 810-820.
5. S. C. R. Lummis, D. L. Beene, L. W. Lee, H. A. Lester, R. W. Broadhurst, D. A. Dougherty, Nature 2005, 438, 248-252.
6. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
7. J. M. Davis, L. K. Tsou, A. D. Hamilton, Chem. Soc. Rev. 2007, 36, 326-334.
8. S. Hecht, I. Huc, Foldamers: Structure, Properties and Applications, Wiley-VCH, Weinheim, 2007.
9. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4012.
10. G. Guichard, I. Huc, Chem. Commun. 2011, 47, 5933-5941.
11. A. Altmayer-Henzien, V. Declerck, J. Farjon, D. Merlet, R. Guillot, D. J. Aitken, Angew. Chem. Int. Ed. 2015, 54, 10807-10810;
12. Angew. Chem. 2015, 127, 10957-10960.
13. R. Lettieri, M. Bischetti, E. Gatto, A. Palleschi, E. Ricci, F. Formaggio, M. Crisma, C. Toniolo, M. Venanzi, Biopolymers 2013, 100, 51-63.
14. M. Crisma, M. DeZotti, F. Formaggio, C. Peggion, A. Moretto, C. Toniolo, J. Pept. Sci. 2015, 21, 148-177.
15. J. Solà, S. P. Fletcher, A. Castellanos, J. Clayden, Angew. Chem. Int. Ed. 2010, 49, 6836-6839;
16. Angew. Chem. 2010, 122, 6988-6991.
17. C. Toniolo, M. Crisma, F. Formaggio, C. Peggion, Biopolymers 2001, 60, 396-419.
18. J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152.
19. C. Toniolo, E. Benedetti, Trends Biochem. Sci. 1991, 16, 350-353.
20. I. L. Karle, P. Balaram, Biochemistry 1990, 29, 6747-6756.
21. C. Toniolo, G. M. Bonora, V. Barone, A. Bavoso, E. Benedetti, B. DiBlasio, P. Grimaldi, F. Lelj, V. Pavone, C. Pedone, Macromolecules 1985, 18, 895-902.
22. B. VenkataramPrasad, P. Balaram, CRC Crit. Rev. Biochem. 1984, 16, 307-348.
23. B. A. F. LeBailly, L. Byrne, V. Diemer, M. Foroozandeh, G. A. Morris, J. Clayden, Chem. Sci. 2015, 6, 2313-2322.
24. R.-P. Hummel, C. Toniolo, G. Jung, Angew. Chem. Int. Ed. Engl. 1987, 26, 1150-1152;
25. Angew. Chem. 1987, 99, 1180-1182.
26. B. Pengo, F. Formaggio, M. Crisma, C. Toniolo, G. M. Bonora, Q. B. Broxterman, J. Kamphuis, M. Saviano, R. Iacovino, F. Rossi, etal., J. Chem. Soc. Perkin Trans. 2 1998, 1651-1657.
27. M. DePoli, L. Byrne, R. A. Brown, J. Solà, A. Castellanos, T. Boddaert, R. Wechsel, J. D. Beadle, J. Clayden, J. Org. Chem. 2014, 79, 4659-4675.
28. B. A. F. LeBailly, J. Clayden, Chem. Commun. 2014, 50, 7949-7952.
29. R. A. Brown, T. Marcelli, M. DePoli, J. Solà, J. Clayden, Angew. Chem. Int. Ed. 2012, 51, 1395-1399;
30. Angew. Chem. 2012, 124, 1424-1428.
31. J. Solà, G. A. Morris, J. Clayden, J. Am. Chem. Soc. 2011, 133, 3712-3715.
32. Y. Inai, Y. Kurokawa, T. Hirabayashi, Biopolymers 1999, 49, 551-564.
33. Y. Inai, Y. Kurokawa, A. Ida, T. Hirabayashi, Bull. Chem. Soc. Jpn. 1999, 72, 55-61.
34. Y. Inai, Y. Kurokawa, N. Kojima, J. Chem. Soc. Perkin Trans. 2 2002, 1850-1857.
35. Y. Inai, S. Ashitaka, T. Hirabayashi, Polym. J. 1999, 31, 246-253.
36. N. Ousaka, Y. Takeyama, H. Iida, E. Yashima, Nat. Chem. 2011, 3, 856-861.
37. L. Byrne, J. Solà, T. Boddaert, T. Marcelli, R. W. Adams, G. A. Morris, J. Clayden, Angew. Chem. Int. Ed. 2014, 53, 151-155;
38. Angew. Chem. 2014, 126, 155-159.
39. Y. Inai, K. Tagawa, A. Takasu, T. Hirabayashi, T. Oshikawa, M. Yamashita, J. Am. Chem. Soc. 2000, 122, 11731-11732.
40. M. Crisma, C. Toniolo, Biopolymers 2015, 104, 46-64.
41. B. Amit, D. A. Ben-Efraim, A. Patchornik, J. Am. Chem. Soc. 1976, 98, 843-844.
42. S. Pass, B. Amit, A. Patchornik, J. Am. Chem. Soc. 1981, 103, 7674-7675.
43. S. P. Fletcher, J. Solà, D. Holt, R. A. Brown, J. Clayden, Beilstein J. Org. Chem. 2011, 7, 1304-1309.
44. H. Sigel, Angew. Chem. Int. Ed. Engl. 1968, 7, 137-138;
45. Angew. Chem. 1968, 80, 124-124.
46. H. Sigel, R. B. Martin, Chem. Rev. 1982, 82, 385-426.
47. T. Ramdahl, US Patent US20130183235 A1, 2013.
48. L. A. Rubenstein, R. J. Zauhar, R. G. Lanzara, J. Mol. Graphics Modell. 2006, 25, 396-409.
49. E. Ritter, M. Elgeti, F. J. Bartl, Photochem. Photobiol. 2008, 84, 911-920.
50. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673.
51. R. Wechsel, J. Maury, J. Fremaux, S. P. France, G. Guichard, J. Clayden, Chem. Commun. 2014, 50, 15006-15009.
52. A. Hamza, G. Schubert, T. Soõs, I. Papai, J. Am. Chem. Soc. 2006, 128, 13151-13160.
53. J. Clayden, A. Lund, L. S. Vallverdu, M. Helliwell, Nature 2004, 431, 966-971.
54. For an example in which chiral monomers induce asymmetric catalysis at remote achiral catalytic sites, see, L. M. S. Takata, H. Iida, K. Shimomura, K. Hayashi, A. A. dosSantos, E. Yashima, Macromol. Rapid Commun. 2015, 36, 2047-2054.
55. V. Blanco, D. A. Leigh, V. Marcos, Chem. Soc. Rev. 2015, 44, 5341-5370.
56. J. Wang, B. L. Feringa, Science 2011, 331, 1429-1432.
57. Y. Sohtome, S. Tanaka, K. Takada, T. Yamaguchi, K. Nagasawa, Angew. Chem. Int. Ed. 2010, 49, 9254-9257;
58. Angew. Chem. 2010, 122, 9440-9443.
59. S. Mortezaei, N. R. Catarineu, J. W. Canary, J. Am. Chem. Soc. 2012, 134, 8054-8057.
60. R. P. Megens, G. Roelfes, Chem. Eur. J. 2011, 17, 8514-8523.
61. M. Suginome, T. Yamamoto, Y. Nagata, T. Yamada, Y. Akai, Pure Appl. Chem. 2012, 84, 1759-1769.