The role of water in the proton transfer reaction mechanism in tryptophan

Journal of Computational Chemistry

Volumn 31, Issue 14, 2010, Pages 2642-2649

  Vöhringer Martinez, Esteban ^a   Toro Labbé, Alejandro ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

proton transfer; reaction force; solvent effect; tryptophan; water catalysis

Indexed keywords

ACTIVATION BARRIERS; AMINO GROUP; BOND FORMATION; CONTINUUM MODEL; ELECTRONIC FLUX; IN-VACUUM; INFLUENCE OF WATER; INTERMOLECULAR REACTIONS; INTRAMOLECULAR PROTON TRANSFER; INTRAMOLECULAR REACTIONS; INTRINSIC REACTION COORDINATE; MEDIATED REACTIONS; NATURAL BOND ORDERS; PROTON TRANSFER REACTION MECHANISMS; PROTON-TRANSFER MECHANISM; REACTION COORDINATES; REACTION FORCES; REACTION MECHANISM; ROLE OF WATER; SOLVENT EFFECT; TRYPTOPHAN; WATER CATALYSIS; WATER MOLECULE;

AMINO ACIDS; CATALYSIS; CONTINUUM MECHANICS; FUNCTIONAL GROUPS; PROTON TRANSFER;

MOLECULES;

PROTON; TRYPTOPHAN; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR DYNAMICS; QUANTUM THEORY;

MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; PROTONS; QUANTUM THEORY; TRYPTOPHAN; WATER;

EID: 78149436417     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21559     Document Type: Article

References (32)

1. Jensen, J.,;, Gordon, M., J Am Chem Soc 1995, 117, 8159.
2. Balta, B.,;, Aviyente, V., J Comput Chem 2004, 25, 690.
3. Tuñón, I.,;, Silla, E.,;, Ruiz-López, M., Chem Phys Lett 2000, 321, 433.
4. Kassab, E.,;, Langlet, J.,;, Evleth, E.,;, Akacem, Y., J Mol Struct 2000, 531, 267.
5. Tortonda, F.,;, PascualAhuir, J.,;, Silla, E.,;, Tunon, I., Chem Phys Lett 1996, 260, 21.
6. Twari, S.,;, Mishra, P. C.,;, Suhai, S., Int J Quantum Chem 2008, 108, 1004.
7. Balta, B.,;, Aviyente, V., J Comput Chem 2003, 24, 1789.
8. Tortonda, F.,;, Silla, E.,;, Tunon, I.,;, Rinaldi, D.,;, Ruiz-Lopez, M., Theor Chem Acc 2000, 104, 89.
9. Park, S.,;, Ahn, D.,;, Lee, S., Chem Phys Lett 2003, 403, 72.
10. Ahn, D.,;, Park, S.,;, Jeon, I.,;, Lee, M.,;, Kim, N.,;, Han, Y.,;, Lee, S., J Phys Chem B 2003, 107, 14109.
11. Meijer, G.,;, Suhai, S.,;, Paizs, B.,;, Oomens, J., J Phys Chem A 2007, 111, 7309.
12. Blancafort, L.,;, Gonzalez, D.,;, Olivucci, M.,;, Robb, M., J Am Chem Soc 2002, 124, 6398.
13. Snoek, L.,;, Kroemer, R.,;, Simons, J., Phys Chem Chem Phys 2002, 4, 2130.
14. Huang, Z.,;, Lin, Z., J Phys Chem A 2005, 109, 2656.
15. Sobolewski, A. L.,;, Shemesh, D.,;, Domcke, W., J Phys Chem A 2009, 113, 542.
16. Toro-Labbe, A., J Phys Chem A 1999, 103, 4398.
17. Toro-Labbe, A.,;, Gutierrerez-Oliva, S.,;, Murray, J. S.,;, Politzer, P., Mol Phys 2007, 105, 2619.
18. Burda, J. V.,;, Toro-Labbe, A.,;, Gutierrez-Oliva, S.,;, Murray, J. S.,;, Politzer, P., J Phys Chem A 2007, 111, 2455.
19. Herrera, B.,;, Toro-Labbe, A., J Phys Chem A 2007, 111, 5921.
20. Echegaray, E.,;, Toro-Labbe, A., J Phys Chem A 2008, 112, 11801.
21. Vogt-Geisse, S.,;, Toro-Labbe, A., J Chem Phys 2009, 130, 244308.
22. Martinez, J.,;, Toro-Labbe, A., J Math Chem 2009, 45, 911.
23. Herrera, B.,;, Toro-Labbe, A., J Chem Phys 2004, 121, 7096.
24. Toro-Labbé, A.,;, Gutiérrez-Oliva, S.,;, Concha, M.,;, Murray, J.,;, Politzer, P., J Chem Phys 2004, 121, 4570.
25. Parr, R. G.,;, Yang, W., Density Functional Theory of Atoms and Molecules; University Press: Oxford, 1989.
26. Janak, J., Phys Rev B Condens Matter Mater Phys 1978, 18, 7165.
27. Frisch, M. J.,;, Trucks, G. W.,;, Schlegel, H. B.,;, Scuseria, G. E.,;, Robb, M. A.,;, Cheeseman, J. R.,;, Montgomery, Jr., J. A.,;, Vreven, T.,;, Kudin, K. N.,;, Burant, J. C.,;, Millam, J. M.,;, Iyengar, S. S.,;, Tomasi, J.,;, Barone, V.,;, Mennucci, B.,;, Cossi, M.,;, Scalmani, G.,;, Rega, N.,;, Petersson, G. A.,;, Nakatsuji, H.,;, Hada, M.,;, Ehara, M.,;, Toyota, K.,;, Fukuda, R.,;, Hasegawa, J.,;, Ishida, M.,;, Nakajima, T.,;, Honda, Y.,;, Kitao, O.,;, Nakai, H.,;, Klene, M.,;, Li, X.,;, Knox, J. E.,;, Hratchian, H. P.,;, Cross, J. B.,;, Bakken, V.,;, Adamo, C.,;, Jaramillo, J.,;, Gomperts, R.,;, Stratmann, R. E.,;, Yazyev, O.,;, Austin, A. J.,;, Cammi, R.,;, Pomelli, C.,;, Ochterski, J. W.,;, Ayala, P. Y.,;, Morokuma, K.,;, Voth, G. A.,;, Salvador, P.,;, Dannenberg, J. J.,;, Zakrzewski, V. G.,;, Dapprich, S.,;, Daniels, A. D.,;, Strain, M. C.,;, Farkas, O.,;, Malick, D. K.,;, Rabuck, A. D.,;, Raghavachari, K.,;, Foresman, J. B.,;, Ortiz, J. V.,;, Cui, Q.,;, Baboul, A. G.,;, Clifford, S.,;, Cioslowski, J.,;, Stefanov, B. B.,;, Liu, G.,;, Liashenko, A.,;, Piskorz, P.,;, Komaromi, I.,;, Martin, R. L.,;, Fox, D. J.,;, Keith, T.,;, Al-Laham, M. A.,;, Peng, C. Y.,;, Nanayakkara, A.,;, Challacombe, M.,;, Gill, P. M. W.,;, Johnson, B.,;, Chen, W.,;, Wong, M. W.,;, Gonzalez, C.,; and, Pople, J. A., Gaussian 03, Revision D.02, Gaussian, Inc., Wallingford CT, 2004.
28. Tomasi, J.,;, Mennucci, B.,;, Cammi, R., Chem Rev 2005, 105, 2999.
29. Foster, J.,;, Weinhold, F., J Am Chem Soc 1980, 102, 7211.
30. Reed, A.,;, Curtiss, L.,;, Weinhold, F., Chem Rev 1988, 88, 899.
31. Glendening, E. D.,;, Reed A. E.,;, Carpenter J. E.,;, Weinhold, F., NBO Program, Version 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WL, 1994.
32. Cossi, M.,;, Mennucci, B.,;, Pitarch, J.,;, Tomasi, J., J Comput Chem 1998, 19, 833.