Hybrid helices: Motifs for secondary structure scaffolds in foldamers

Journal of the American Chemical Society

Volumn 131, Issue 47, 2009, Pages 17335-17344

  Sharma, Gangavaram V M ^a   Chandramouli, Nagula ^a   Choudhary, Madavi ^a   Nagendar, Pendem ^a   Ramakrishna, Kallaganti V S ^a   Kunwar, Ajit C ^a   Schramm, Peter ^b   Hofmann, Hans Jörg ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FOLDAMERS; HYBRID PEPTIDES; SECONDARY STRUCTURES;

AMINES; AMPHIPHILES; SCAFFOLDS;

PEPTIDES;

OLIGOMER; SCAFFOLD PROTEIN;

ARTICLE; MOLECULAR MIMICRY; PROTEIN ANALYSIS; PROTEIN MOTIF; PROTEIN SECONDARY STRUCTURE; STRUCTURE ANALYSIS;

MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; PROTEINS;

EID: 72249096678     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907074u     Document Type: Article

References (55)

1. (a) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
2. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071-13072.
3. Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941.
4. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
5. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
6. (c) Kirschenbaum, K.; Zuckerman, R. N.; Dill, D. A. Curr. Opin. Struct. Biol. 1999, 9, 530-535.
7. (d) Stigers, K. D.; Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1999, 3, 714-723.
8. (e) Smith, M. D.; Fleet, G. W. J. J. Pept. Sci. 1999, 5, 425-441.
9. (f) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
10. (g) Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131-3152.
11. (h) Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650-653.
12. (i) Martinek, T. A.; Fülöp, F. Eur. J. Biochem. 2003, 270, 3657-3666.
13. (j) Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111-1239.
14. (k) Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Nature Chem. Biol. 2007, 3, 252-262.
15. (l) Hecht, S., Huc, I., Eds.; Foldamers: Structure, Properties and Applications; Wiley-VCH: Weinheim, Germany, 2007.
16. (m) Brenner, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 1181-1189.
17. (n) Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 983-1002.
18. (o) Hanessian, S.; Luo, X. H.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569-8570.
19. (p) Hanessian, S.; Luo, X. H.; Schaum, R. Tetrahedron Lett. 1999, 40, 4925-4929.
20. (q) Vasudev, P. G.; Shamala, N.; Ananda, K.; Balaram, P. Angew. Chem., Int. Ed. 2005, 44, 4972-4975.
21. (r) Grison, C.; Coutrot, P.; Geneve, C.; Didierjean, C.; Marraud, M. J. Org. Chem. 2005, 70, 10753-10764.
22. (s) Szabo, L.; Smith, B. L.; McReynolds, K. D.; Parrill, A. L.; Morris, E. R.; Gervay, J. J. Org. Chem. 1998, 63, 1074-1078.
23. (t) Möhle, K.; Günther, R.; Thormann, M.; Sewald, N.; Hofmann, H.-J. Biopolymers 1999, 50, 167-184.
24. (u) Wu, Y.-D.; Wang, D.-P. J. Am. Chem. Soc. 1998, 120, 13485-13493.
25. (v) Wu, Y.-D.; Han, W.; Wang, D.-P.; Gao, Y.; Zhao, Y.-L. Acc. Chem. Res. 2008, 41, 1418-1427.
26. (w) Baldauf, C.; Günther, R.; Hofmann, H.-J. Helv. Chim. Acta 2003, 86, 2573-2588.
27. (x) Baldauf, C.; Günther, R.; Hofmann, H.-J. J. Org. Chem. 2004, 69, 6214-6220.
28. (a) Schmitt, M. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2004, 126, 6848-6849.
29. (b) Sadowsky, J. D.; Schmitt, M. A.; Lee, H. S.; Umezawa, N.; Wang, S.; Tomita, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11966-11968.
30. (c) Horne, W. S.; Price, J. L.; Keck, J. L.; Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 4178-4180.
31. (d) Price, J. L.; Horne, W. S.; Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 6376-6377.
32. (e) Seebach, D.; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366-1375.
33. (f) David, R.; Günther, R.; Baumann, L.; Lühmann, T.; Seebach, D.; Hofmann, H.-J.; Beck-Sickinger, A. G. J. Am. Chem. Soc. 2008, 130, 15311-15317.
34. (g) Sadowsky, J. D.; Fairlie, W. D.; Hadley, E. B.; Lee, H. S.; Umezawa, N.; Nikolovska-Coleska, Z.; Wang, S.; Huang, D. C. S.; Tomita, Y.; Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 139-154.
35. (h) Lee, E. F.; Sadowsky, J. D.; Smith, B. J.; Czabotar, P. E.; Peterson-Kauman, K. J.; Colman, P. M.; Gellman, S. H.; Fairlie, W. D. Angew. Chem., Int. Ed. 2009, 48, 4318-4322.
36. Sharma, G. V. M.; Reddy, V. G.; Chander, A. S.; Reddy, K. R. Tetrahedron Asymmetry 2002, 13, 21-24.
37. (a) Sharma, G. V. M.; Reddy, K. R.; Krishna, P. R.; Sankar, A. R.; Narsimulu, K.; Kumar, S. K; Jayaprakash, P.; Jagannadh, B.; Kunwar, A. C. J. Am. Chem. Soc. 2003, 125, 13670-13671.
38. (b) Sharma, G. V. M.; Reddy, K. R.; Krishna, P. R.; Sankar, A. R.; Jayaprakash, P.; Jagannadh, B.; Kunwar, A. C. Angew. Chem., Int. Ed. 2004, 43, 3961-3965.
39. Hayen, A.; Schmitt, M. A.; Nagassa, N.; Thomson, K. A.; Gellman, S. H. Angew. Chem., Int. Ed. 2004, 43, 505-510.
40. De Pol, S.; Zorn, C.; Klein, C. D.; Zerbe, O.; Reiser, O. Angew. Chem., Int. Ed. 2004, 43, 511-514.
41. Horne, W. S.; Gellman, S. H. Acc. Chem. Res. 2008, 41, 1399-1408.
42. (a) Sharma, G. V. M.; Nagendar, P.; Jayaprakash, P.; Krishna, P. R.; Ramakrishna, K. V. S.; Kunwar, A. C. Angew. Chem., Int. Ed. 2005, 44, 5878-5882.
43. (b) Srinivasulu, G.; Kumar, S. K.; Sharma, G. V. M.; Kunwar, A. C. J. Org. Chem. 2006, 71, 8395-8400.
44. (c) Baldauf, C.; Günther, R.; Hofmann, H.-J. Biopolymers 2006, 84, 408-413.
45. Sharma, G. V. M.; Nagendar, P.; Ramakrishna, K. V. S.; Chandramouli, N.; Choudhary, M.; Kunwar, A. C. Chem. Asian J. 2008, 3, 969-983.
46. (a) Sharma, G. V. M.; Jadhav, V. B.; Ramakrishna, K. V. S.; Jayaprakash, P.; Narsimulu, K.; Subash, V.; Kunwar, A. C. J. Am. Chem. Soc. 2006, 128, 14657-14668.
47. (b) Baldauf, C.; Günther, R.; Hofmann, H.-J. J. Org. Chem. 2006, 71, 1200-1208.
48. (c) Sharma, G. V. M.; Babu, B. S.; Ramakrishna, K. V. S.; Nagendar, P.; Kunwar, A. C.; Schramm, P.; Baldauf, C.; Hofmann, H.-J. Chem. - Eur. J. 2009, 15, 5552-5566.
49. (d) Sharma, G. V. M.; Babu, B. S.; Deepak, C.; Ramakrishna, K. V. S.; Kunwar, A. C.; Schramm, P.; Baldauf, C.; Hofmann, H.-J. J. Org. Chem. 2009, 74, 6703-6713.
50. (a) Chan, L. C.; Cox, G. B. J. Org. Chem. 2007, 72, 8863-8869.
51. (b) Bodanszky, M. Peptide Chemistry: A Practical Textbook, Springer: New York, 1988.
52. See Supporting information.
53. 3 solutions of the peptides.
54. Brown, J. H.; Kim, K.-H.; Jun, G.; Greenfield, N. J.; Dominguez, R.; Volkmann, N.; Hitchcock-DeGregori, S. E.; Cohen, C. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 8496-8501.
55. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian Inc.: Wallingford, CT, 2004.