Insertion of methylene units into the turn segment of designed β- hairpin peptides

Journal of the American Chemical Society

Volumn 121, Issue 23, 1999, Pages 5360-5363

  Shankaramma, S C ^a   Singh, S Kumar ^a   Sathyamurthy, Aruna ^a   Balaram, P ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR DYNAMICS; PEPTIDE ANALYSIS; PROTEIN DEGRADATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033575129     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990412b     Document Type: Article

References (41)

1. (a) Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015-2022.
2. (b) Banerjee, A.; Balaram, P. Curr. Sci. 1997, 73, 1067-1077.
3. (c) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
4. (a) Goodman, M.; Ro, S. In Medicinal Chemistry and Drug Design; Burger, A., Ed.; John Wiley & Sons: New York, 1994; Vol. I, pp 803-861.
5. (b) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219-266.
6. (a) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer H. Helv. Chim. Acta 1996, 79, 913-941.
7. (b) Daura, X.; Van Gunsteren, W. F.; Rigo, D.; Jaun, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410-1417.
8. (c) Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 983-1002.
9. (d) Apella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071-13072.
10. (e) Apella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381-382.
11. (f) Krauthaser, S.; Christianson, L. A.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 11719-11720.
12. (g) Wu, Y. D.; Wang, D. P. J. Am. Chem. Soc. 1998, 120, 13485-13493.
13. (h) Gademann, K.; Jaun, B.; Seebach, D.; Perozzo, R.; Scapozza, L.; Folkers, G. Helv. Chim. Acta 1999, 82, 1-11.
14. (i) Gung, B. W.; Mackay, J.; Zou, D. J. Org. Chem. 1999, 64, 700-706.
15. (a) Snyder, K. R.; Murray, T. F.; DeLander, G. E.; Aldrich, J. V. J. Med. Chem. 1993, 36, 1100-1103.
16. (b) Seebach, D.; Abele, S.; Sifferlen, T.; Hanggi, M.; Gruner, S.; Seiler, P. Helv. Chim. Acta 1998, 81, 2218-2243.
17. (c) Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507-2508.
18. (d) Hanessian, S.; Luo, X.; Schaun, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569-8570.
19. (e) Szabo, L.; Smith, B. L.; McReynolds, K. D.; Parill, A. L.; Morris, E. R.; Gervay, J. J. Org. Chem. 1998, 63, 1074-1078.
20. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087-9095.
21. (a) Raghothama, S.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137-143.
22. (b) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4869-4870.
23. (c) Struthers, M. D.; Cheng, R. P.; Imperiali, B. Science 1996, 271, 342-345.
24. (d) Das, C.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1998, 120, 5812-5813.
25. Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189-8193.
26. (a) Homomorphous segments are defined as having the same number of backbone atoms between the -NH and C=O groups of the ω-amino acids.
27. (b) Banerjee, A.; Pramanik, A.; Bhattacharjya, S.; Balaram, P. Biopolymers 1996, 39, 769-777.
28. Gunasekaran, K.; Ramakrishnan, C.; Balaram, P. Protein Eng. 1997, 10, 1131-1141.
29. Awasthi, S. K.; Raghothama, S.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1996, 2701-2706.
30. Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375-381.
31. Alvarado, M. R.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604-612.
32. Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836-5845.
33. The nomenclature for the dihedral angles in δ-Ava is as defined in ref 8. See also refs 1b and 5 for a suggestion regarding nomenclature for ω-amino acids in general.
34. Gunasekaran, K.; Gomathi, L.; Ramakrishnan, C.; Chandrasekhar, J.; Balaram, P. J. Mol. Biol. 1998, 284, 1505-1516.
35. (a) Chung, Y. J.; Christianson, L. A.; Stanger, H. E.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 10555-10556.
36. (b) Jones, I. G.; Jones, W.; North, M. J. Org. Chem. 1998, 63, 1505-1513.
37. (c) Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Pedone, C.; Iserniac, C.; Pavone, V. Biopolymers 1996, 38, 683-691.
38. (d) Mantsch, H. H.; Perczel, A.; Hollosi, M.; Fasman, G. D. Biopolymers 1993, 33, 201-207.
39. (a) Aleman, C.; Navarro, E.; Puiggali, J. J. Org. Chem. 1995, 60, 6135-6140.
40. (b) Navarro, E.; Aleman, C.; Puiggali, J. J. Am. Chem. Soc. 1995, 117, 7307-7310.
41. (c) Price, D. J.; Roberts, J. D.; Jorgenson, W. L. J. Am. Chem. Soc. 1998, 120, 9672-9679.