Crystallographic characterization of 12-helical secondary structure in β-peptides containing side chain groups

Journal of the American Chemical Society

Volumn 132, Issue 39, 2010, Pages 13879-13885

  Choi, Soo Hyuk ^a,b   Guzei, Ilia A ^a   Spencer, Lara C ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL FUNCTIONS; CONFORMATIONAL BEHAVIOR; CRYSTALLOGRAPHIC CHARACTERIZATION; FIVE-MEMBERED RINGS; FOLDAMERS; HELICAL CONFORMATION; HELICAL FOLDING; HELICAL PARAMETERS; HOMO-OLIGOMERS; INTERNAL HYDROGEN BONDS; PEPTIDE BACKBONES; SECONDARY STRUCTURES; SIDE CHAINS; STRUCTURAL PARAMETER; TORSION ANGLE;

AMINO ACIDS; AMPHIPHILES; CONFORMATIONS; HYDROGEN; HYDROGEN BONDS; ORGANIC ACIDS;

PEPTIDES;

2 AMINOCYCLOPENTANECARBOXYLIC ACID; BETA AMINO ACID; PEPTIDE;

ALPHA HELIX; ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; CRYSTALLOGRAPHY; DIPOLE; HYDROGEN BOND; PEPTIDE ANALYSIS; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 77957302949     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1062532     Document Type: Article

References (44)

1. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173
2. Cheng, R. P., Gellman, S. H., and DeGrado, W. F. Chem. Rev. 2001, 101, 3219
3. Seebach, D., Hook, D. F., and Glattli, A. Biopolymers 2006, 84, 23
4. Crisma, M., Formaggio, F., Moretto, A., and Toniolo, C. Biopolymers 2006, 84, 3
5. Wu, Y. D. and Wang, D. P. J. Am. Chem. Soc. 1999, 121, 9352
6. Gunther, R., Hofmann, H. J., and Kuczera, K. J. Phys. Chem. B 2001, 105, 5559
7. Beke, T., Somlai, C., and Perczel, A. J. Comput. Chem. 2006, 27, 20
8. Appella, D. H., Christianson, L. A., Klein, D. A., Powell, D. R., Huang, X. L., Barchi, J. J., and Gellman, S. H. Nature 1997, 387, 381
9. Applequist, J., Bode, K. A., Appella, D. H., Christianson, L. A., and Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4891
10. Appella, D. H., Christianson, L. A., Klein, D. A., Richards, M. R., Powell, D. R., and Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 7574
11. Barchi, J. J., Huang, X. L., Appella, D. H., Christianson, L. A., Durell, S. R., and Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 2711
12. Wang, X. F., Espinosa, J. F., and Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 4821
13. Lee, H. S., Syud, F. A., Wang, X. F., and Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 7721
14. LePlae, P. R., Fisk, J. D., Porter, E. A., Weisblum, B., and Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 6820
15. Woll, M. G., Fisk, J. D., LePlae, P. R., and Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 12447
16. Park, J. S., Lee, H. S., Lai, J. R., Kim, B. M., and Gellman, S. H. J. Am. Chem. Soc. 2003, 125, 8539
17. Peelen, T. J., Chi, Y. G., English, E. P., and Gellman, S. H. Org. Lett. 2004, 6, 4411
18. Hetényi, A., To'th, G. K., Somlai, C., Vass, E., Martinek, T. A., and Fülöp, F. Chem. - Eur. J. 2009, 15, 10736
19. Hetényi, A., Szakonyi, Z., Mándity, I. M., Szolnoki, É., To'th, G. K., Martinek, T. A., and Fülöp, F. Chem. Commun. 2009, 177
20. While our paper was under review, a very thorough characterization of 12-helix formation by oligomers of trans -2-aminocyclobutanecarboxylic acid appeared: Fernandes, C., Faure, S., Pereira, E., Théry, V., Declerck, V., Guillot, R., and Aitken, D. J. Org. Lett. 2010, 12, 3606 - 3609. The crystal structure reported by Aitken et al. is not included in our structural analysis. See also: Winkler, J. D., Piatnitski, E. L., Mehlmann, J., Kasparec, J., and Axelsen, P. H. Angew. Chem. Int. Ed. 2001, 40, 743
21. Porter, E. A., Wang, X. F., Lee, H. S., Weisblum, B., and Gellman, S. H. Nature 2000, 404, 565
22. Porter, E. A., Weisblum, B., and Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324
23. English, E. P., Chumanov, R. S., Gellman, S. H., and Compton, T. J. Biol. Chem. 2006, 281, 2661
24. Imamura, Y., Watanabe, N., Umezawa, N., Iwatsubo, T., Kato, N., Tomita, T., and Higuchi, T. J. Am. Chem. Soc. 2009, 131, 7353
25. Simpson, G. L., Gordon, A. H., Lindsay, D. M., Promsawan, N., Crump, M. P., Mulholland, K., Hayter, B. R., and Gallagher, T. J. Am. Chem. Soc. 2006, 128, 10638
26. Kiss, L., Kazi, B., Forro', E., and Fülöp, F. Tetrahedron Lett. 2008, 49, 339
27. Menegazzo, I., Fries, A., Mammi, S., Galeazzi, R., Martelli, G., Orena, M., and Rinaldi, S. Chem. Commun. 2006, 4915
28. Chandrasekhar, S., Reddy, G. P. K., Kiran, M. U., Nagesh, C., and Jagadeesh, B. Tetrahedron Lett. 2008, 49, 2969
29. An alternative secondary structure has been observed for an AZT-derived subunits in a different solvent: Threlfall, R., Davies, A., Howarth, N. M., Fisher, J., and Cosstick, R. Chem. Commun. 2008, 585
30. Moretto, V., Crisma, M., Bonora, G. M., Toniolo, C., Balaram, H., and Balaram, P. Macromolecules 1989, 22, 2939
31. Choi, S. H., Guzei, I. A., and Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 13780
32. Choi, S. H., Guzei, I. A., Spencer, L. C., and Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 6544
33. Choi, S. H., Guzei, I. A., Spencer, L. C., and Gellman, S. H. J. Am. Chem. Soc. 2009, 131, 2917
34. Lee, H. S., LePlae, P. R., Porter, E. A., and Gellman, S. H. J. Org. Chem. 2001, 66, 3597
35. LePlae, P. R., Umezawa, N., Lee, H.-S., and Gellman, S. H. J. Org. Chem. 2001, 66, 5629
36. Horne, W. S., Price, J. L., and Gellman, S. H. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 9151
37. Hayen, A., Schmitt, M. A., Ngassa, F. N., Thomasson, K. A., and Gellman, S. H. Angew. Chem., Int. Ed. 2004, 43, 505
38. Karle, I. L. and Balaram, P. Biochemistry 1990, 29, 6747
39. Toniolo, C. and Benedetti, E. Trends Biochem. Sci. 1991, 16, 350
40. Ramachandran, G. N. and Sasisekharan, V. Adv. Protein Chem. 1968, 23, 283
41. Appella, D. H., Christianson, L. A., Karle, I. L., Powell, D. R., and Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206
42. Sugeta, H. and Miyazawa, T. Biopolymers 1967, 5, 673
43. Kahn, P. C. Comput. Chem. 1989, 13, 185
44. Barlow, D. J. and Thornton, J. M. J. Mol. Biol. 1988, 201, 601