Intramolecular amide stacking and its competition with hydrogen bonding in a small foldamer

Journal of the American Chemical Society

Volumn 131, Issue 40, 2009, Pages 14243-14245

  James III, William H ^a   Müller, Christian W ^a   Buchanan, Evan G ^a   Nix, Michael G D ^a,b   Guo, Li ^c   Roskop, Luke ^d   Gordon, Mark S ^d   Slipchenko, Lyudmila V ^a   Gellman, Samuel H ^c   Zwier, Timothy S ^a  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF YORK   (United Kingdom)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE GROUPS; CARBOXAMIDES; CHEMICAL EQUATIONS; H-BONDING; HYDROGEN BONDINGS; INFRARED SPECTRUM; ISOLATED MOLECULES; STACKING CONFIGURATIONS; STACKING INTERACTION;

AMIDES; AMINES; AMPHIPHILES; CHEMICAL REACTIONS; HYDROGEN; HYDROGEN BONDS; INFRARED SPECTROSCOPY;

CONFORMATIONS;

AMIDE; BETA AMINO ACID; C PEPTIDE;

ARTICLE; HYDROGEN BOND; IONIZATION; IRRADIATION; PROTEIN STRUCTURE; ULTRAVIOLET SPECTROSCOPY;

AMIDES; HYDROGEN BONDING; MODELS, MOLECULAR; PEPTIDES; PROTEIN FOLDING; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 70349941376     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9054965     Document Type: Article

References (23)

1. Cantor, C. R. ; Schimmenl, P. R. Biophysical Chemistry: I. The Conformation of Biological Macromolecules; W. H. Freeman and Co.: San Francisco, 1980.
2. Choudhary, A.; Gandla, D.; Krow, G. R.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 7244.
3. Yonezawa, T.; Morishim., I. B. Chem. Soc. Jpn. 1966, 39, 2346.
4. Rabinovitz, M.; Pines, A. J. Chem. Soc. B 1968, 1110.
5. Betson, M. S.; Clayden, J.; Lam, H. K.; Helliwell, M. Angew. Chem., Int. Ed. 2005, 44, 1241.
6. Clayden, J. Chem. Soc. Rev. 2009, 38, 817.
7. Maccallum, P. H.; Poet, R.; Milnerwhite, E. J. J. Mol. Biol. 1995, 248, 361.
8. Maccallum, P. H.; Poet, R.; Milnerwhite, E. J. J. Mol. Biol. 1995, 248, 374.
9. Hinderaker, M. P.; Raines, R. T. Protein Sci. 2003, 12, 1188.
10. Fischer, F. R.; Wood, P. A.; Allen, F. H.; Diederich, F. P. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 17290.
11. Chin, W.; Piuzzi, F.; Dimicoli, I.; Mons, M. Phys. Chem. Chem. Phys. 2006, 8, 1033.
12. Baquero, E. E.; James, W. H.; Choi, S. H.; Gellman, S. H.; Zwier, T. S. J. Am. Chem. Soc. 2008, 130, 4784.
13. Baquero, E. E.; James, W. H.; Choi, S. H.; Gellman, S. H.; Zwier, T. S. J. Am. Chem. Soc. 2008, 130, 4795.
14. James, W. H.; Baquero, E. E.; Shubert, V. A.; Choi, S. H.; Gellman, S. H.; Zwier, T. S. J. Am. Chem. Soc. 2009, 131, 6574.
15. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289.
16. Frisch, M. J., Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
17. Deev, V.; Collins, M. A. J. Chem. Phys. 2005, 122, 154102.
18. Gordon, M. S.; Mullin, J. M.; Pruitt, S. R.; Roskop, L. B.; Slipchenko, L. V.; Boatz, J. A. J. Phys. Chem. B 2009, 113, 9646.
19. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
20. Gordon, M. S.; Freitag, M. A.; Bandyopadhyay, P.; Jensen, J. H.; Kairys, V.; Stevens, W. J. J. Phys. Chem. A 2001, 105, 293.
21. Gordon, M. S.; Slipchenko, L. V.; Li, H.; Jensen, J. H. Ann. Rep. Comput. Chem. 2007, 3, 177.
22. Slipchenko, L. V.; Gordon, M. S. J. Comput. Chem. 2007, 28, 276.
23. Dian, B. C.; Longarte, A.; Winter, P. R.; Zwier, T. S. J. Chem. Phys. 2004, 120, 133.