Hydration of protonated aromatic amino acids: Phenylalanine, tryptophan, and tyrosine

Journal of the American Chemical Society

Volumn 131, Issue 13, 2009, Pages 4695-4701

  Gao, Bing ^a   Wyttenbach, Thomas ^a   Bowers, Michael T ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID SYSTEMS; AMMONIUM GROUPS; AROMATIC AMINO ACID; BOUND WATERS; CARBOXYL GROUPS; CHARGE-DIPOLE; DIPOLE DIPOLE INTERACTIONS; DRIFT CELLS; ELECTRONIC STRUCTURE CALCULATIONS; HIGH WATER; PROTONATED; SEQUENTIAL ADDITION; SIDE CHAINS; SOLVATION SHELL; WATER MOLECULE;

AMINATION; AMINES; AMINO ACIDS; AMMONIUM COMPOUNDS; AROMATIC COMPOUNDS; BINDING ENERGY; BINDING SITES; CELL MEMBRANES; ELECTRONIC STRUCTURE; HYDRATES; HYDRATION; MASS SPECTROMETRY; MOLECULAR MECHANICS; ORGANIC ACIDS;

MOLECULES;

AROMATIC AMINO ACID; PHENYLALANINE; TRYPTOPHAN; TYROSINE; WATER;

ARTICLE; DIPOLE; HYDRATION; HYDROPHILICITY; MASS SPECTROMETRY; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; PROCEDURES; QUANTUM THEORY; THERMODYNAMICS;

BINDING SITES; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENYLALANINE; QUANTUM THEORY; THERMODYNAMICS; TRYPTOPHAN; TYROSINE; WATER;

EID: 67749120540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8085017     Document Type: Article

References (49)

1. Pace, C. N.; Trevino, S.; Prabhakaran, E.; Scholtz, J. M. Philos. Trans. R. Soc. B 2004, 359, 1225-1234.
2. Mattos, C.; Clark, A. C. Arch. Biochem. Biophys. 2008, 469, 118- 131.
3. Shortle, D. Nat. Struct. Biol. 1999, 6, 203-205.
4. Cheung, M. S.; Garcia, A. E.; Onuchic, J. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 685-690.
5. Brun, L.; Isom, D. G.; Velu, P.; Garcia-Moreno, B.; Royer, C. A. Biochemistry 2006, 45, 3473-3480.
6. Papoian, G. A.; Ulander, J.; Eastwood, M. P.; Luthey-Schulten, Z.; Wolynes, P. G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 3352-3357.
7. Ball, P. Chem. Rev. 2008, 108, 74-108.
8. Fullerton, G. D.; Cameron, I. L. Methods Enzymol. 2007, 428, 1-ff.
9. Wyttenbach, T.; Bowers, M. T. Annu. Rev. Phys. Chem. 2007, 58, 511-533.
10. Baumketner, A.; Bernstein, S. L.; Wyttenbach, T.; Bitan, G.; Teplow, D. B.; Bowers, M. T.; Shea, J. E. Protein Sci. 2006, 15, 420-428.
11. Bernstein, S. L.; Wyttenbach, T.; Baumketner, A.; Shea, J. E.; Bitan, G.; Teplow, D. B.; Bowers, M. T. J. Am. Chem. Soc. 2005, 127, 2075- 2084.
12. Liu, D. F.; Wyttenbach, T.; Barran, P. E.; Bowers, M. T. J. Am. Chem. Soc. 2003, 125, 8458-8464.
13. Wyttenbach, T.; Paizs, B.; Barran, P.; Breci, L.; Liu, D. F.; Suhai, S.; Wysocki, V. H.; Bowers, M. T. J. Am. Chem. Soc. 2003, 125, 13768- 13775.
14. Liu, D. F.; Wyttenbach, T.; Carpenter, C. J.; Bowers, M. T. J. Am. Chem. Soc. 2004, 126, 3261-3270.
15. Wyttenbach, T.; Liu, D. F.; Bowers, M. T. Int. J. Mass Spectrom. 2005, 240, 221-232.
16. Wincel, H. Int. J. Mass Spectrom. 2006, 251, 23-31.
17. Wincel, H. Chem. Phys. Lett. 2007, 439, 157-161.
18. Meotner, M.; Field, F. H. J. Am. Chem. Soc. 1974, 96, 3168-3171.
19. Blades, A. T.; Klassen, J. S.; Kebarle, P. J. Am. Chem. Soc. 1996, 118, 12437-12442.
20. Kohtani, M.; Breaux, G. A.; Jarrold, M. F. J. Am. Chem. Soc. 2004, 126, 1206-1213.
21. Michaux, C.; Wouters, J.; Jacquemin, D.; Perpete, E. A. Chem. Phys. Lett. 2007, 445, 57-61.
22. Rozman, M. J. Am. Soc. Mass Spectrom. 2005, 16, 1846-1852.
23. Lemoff, A. S.; Williams, E. R. J. Am. Soc. Mass Spectrom. 2004, 15, 1014-1024.
24. Lemoff, A. S.; Bush, M. F.; Wu, C. C.; Williams, E. R. J. Am. Chem. Soc. 2005, 127, 10276-10286.
25. Kamariotis, A.; Boyarkin, O. V.; Mercier, S. R.; Beck, R. D.; Bush, M. F.; Williams, E. R.; Rizzo, T. R. J. Am. Chem. Soc. 2006, 128, 905-916.
26. Boyarkin, O. V.; Mercier, S. R.; Kamariotis, A.; Rizzo, T. R. J. Am. Chem. Soc. 2006, 128, 2816-2817.
27. Mercier, S. R.; Boyarkin, O. V.; Kamariotis, A.; Guglielmi, M.; Tavernelli, I.; Cascella, M.; Rothlisberger, U.; Rizzo, T. R. J. Am. Chem. Soc. 2006, 128, 16938-16943.
28. Wyttenbach, T.; Kemper, P. R.; Bowers, M. T. Int. J. Mass Spectrom. 2001, 212, 13-23.
29. Gao, B.; Liu, Z. F. J. Chem. Phys. 2005, 123, 224302.
30. Bleiholder, C.; Osburn, S.; Williams, T. D.; Suhai, S.; Stipdonk, M. V.; Harrison, A. G.; Paizs, B. J. Am. Chem. Soc. 2008, 130, 17774-17789.
31. Case, D. A.; et al. Amber 8; University of California, San Francisco, 2004.
32. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
33. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031.
34. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
35. Wyttenbach, T.; vonHelden, G.; Bowers, M. T. J. Am. Chem. Soc. 1996, 118, 8355-8364.
36. quot;Interactions" refers here to van der Waals interactions in the broadest sense, including (possibly weak) hydrogen bonds.
37. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
38. At the B3LYP level of theory, the H(3)-side chain interaction is 2 kcal/mol stronger than the H(2)-carboxyl interaction, based on a comparison of structures having one or the other type of interaction. This result indicates that the H(3)-side chain interaction is significant and of the same order as the H(2)-carboxyl interaction or stronger.
39. Rodham, D. A.; Suzuki, S.; Suenram, R. D.; Lovas, F. J.; Dasgupta, S.; Goddard, W. A.; Blake, G. A. Nature 1993, 362, 735-737.
40. Zwier, T. S. Annu. Rev. Phys. Chem. 1996, 47, 205-241.
41. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2000, 122, 11450-11458.
42. Mons, M.; Dimicoli, I.; Tardivel, B.; Piuzzi, F.; Brenner, V.; Millie, P. Phys. Chem. Chem. Phys. 2002, 4, 571-576.
43. Vaupel, S.; Brutschy, B.; Tarakeshwar, P.; Kim, K. S. J. Am. Chem. Soc. 2006, 128, 5416-5426.
44. Perutz, M. F.; Fermi, G.; Abraham, D. J.; Poyart, C.; Bursaux, E. J. Am. Chem. Soc. 1986, 108, 1064-1078.
45. Chakrabarti, P.; Bhattacharyya, R. Prog. Biophys. Mol. Biol. 2007, 95, 83-137.
46. A structure with three water molecules in the first solvation shell (like structure F) and one water in the second shell is detected, but found to be energetically less favorable than structure G (by 2-3 kcal/mol).
47. Structure H, corresponding to structure G with an additional fifth water molecule bound to water attached to H(2) and H(3), is the lowestenergy structure located for a five-water complex. However, additional structures in the same family (G plus one water in the second solvation shell) include structures with a fifth water molecule bound between H(3) and H(1) and between H(1) and H(2) with similar energies (isoenergetic within 1-2 kcal/mol).
48. Kemper, P. R.; Weis, P.; Bowers, M. T.; Maitre, P. J. Am. Chem. Soc. 1998, 120, 13494-13502.
49. Manard, M. J.; Kemper, P. R.; Bowers, M. T. Int. J. Mass Spectrom. 2005, 241, 109-117.