On the formation of radical dications of protonated amino acids in a "microsolution" of water or acetonitrile and their reactivity towards the solvent

Chemistry - A European Journal

Volumn 7, Issue 15, 2001, Pages 3214-3222

  Sørensen, Martin ^a   Forster, James S ^c   Hvelplund, Preben ^a   Jørgensen, Thomas J D ^b   Nielsen, Steen Brøndsted ^a   Tomita, Shigeo ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c MCMASTER UNIVERSITY   (Canada)

Author keywords

Amino acids; Density functional calculations; High energy collisions; Solvation

Indexed keywords

ACETONITRILE; HYDRATION; PROTONS; SOLVENTS; WATER;

PROTONATION;

AMINO ACIDS;

ACETONITRILE; ACETONITRILE DERIVATIVE; AMINO ACID; AMINO ACID DERIVATIVE; CATION; PROTON; SOLVENT; TYROSINE; WATER;

ARTICLE; CALCULATION; CHEMICAL MODEL; CHEMICAL REACTION; CHEMISTRY; ELECTRON TRANSPORT; ENERGY TRANSFER; IONIZATION; PROTON TRANSPORT; SOLUTION AND SOLUBILITY; SOLVATION;

ACETONITRILES; AMINO ACIDS; MODELS, CHEMICAL; PROTONS; SOLUTIONS; WATER;

EID: 1442318934     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010803)7:15<3214::AID-CHEM3214>3.0.CO;2-7     Document Type: Article

References (59)

1. a) M. F. Jarrold, Acc. Chem. Res. 1999, 32, 360;
2. b) C. S. Hoaglund-Hyzer, A. E. Counterman, D. E. Clemmer, Chem. Rev. 1999, 99, 3037 and references therein;
3. c) Y. Mao, M. A. Ratner, M. F. Jarrold, J. Am. Chem. Soc. 2000, 122, 2950;
4. d) A. C. Gill, K. R. Jennings, T. Wyttenbach, M. T. Bowers, Int. J. Mass Spectrom. 2000, 196, 685;
5. e) T. J. D. Jørgensen, D. Delforge, J. Remacle, G. Bojesen, P. Roepstorff, Int. J. Mass Spectrom. 1999, 188, 63;
6. f) A. A. Rostom, J. R. H. Tame, J. E. Ladbury, C. V. Robinson, J. Mol. Biol. 2000, 290, 269;
7. g) R. R. Hudgins, M. F. Jarrold, J. Am. Chem. Soc. 1999, 121, 3494;
8. h) P. J. Steinbach, B. R. Brooks, Proc. Natl Acad. Sci. USA 1993, 90, 9135.
9. a) S. E. Rodriguez-Cruz, J. S. Klassen, E. R. Williams, J. Am. Soc. Mass Spectrom. 1999, 10, 958;
10. b) S. E. Rodriguez-Cruz, J. S. Klassen, E. R. Williams, J. Am. Soc. Mass Spectrom. 1999, 8, 565;
11. c) S. K. Chowdhury, V. Katta, B. T. Chait, Rapid Commun. Mass Spectrom. 1990, 4, 81;
12. d) R. D. Smith, K. J. Light-Wahl, Biol. Mass Spectrom. 1993, 22, 493;
13. e) S.-W. Lee, P. Freivogel, T. Schindler, J. L. Beauchamp, J. Am. Chem. Soc. 1998, 120, 11 758.
14. J. S. Klassen, A. T. Blades, P. Kebarle, J. Phys. Chem. 1995, 99, 15 509.
15. D. Zhan, J. Rosell, J. B. Fenn, J. Am. Soc. Mass Spectrom. 1998, 9, 1241.
16. a) M. R. A. Blomberg, P. E. M. Siegbahn, S. Styring, G. T. Babcock, B. Åkermark, P. Korall, J. Am. Chem. Soc. 1997, 119, 8285;
17. b) M. R. A. Blomberg, P. E. M. Siegbahn, Mol. Phys. 1999, 96, 571.
18. a) W. Kaim, B. Schwederski, Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life. An Introduction and Guide, Wiley, Chichester, 1997;
19. b) L. Stryer, Biochemistry, 3rd ed., Freeman, New York, 1988;
20. c) C. Aubert, M. H. Vos, P. Mathis, A. P. M. Eker, K. Brettel, Nature 2000, 405, 586.
21. J. Stubbe, W. van der Donk, Chem. Rev. 1998, 95, 705.
22. 2 (both doublet states) are slightly more efficient than the other target gases being in singlet ground states [P. O. Danis, R. Feng, F. W. McLafferty, Anal. Chem. 1986, 58, 355].
23. Š. Beranová, J. Cai, C. Wesdemiotis, J. Am. Chem. Soc. 1995, 117, 9492.
24. 2.
25. M. J. Polce, C. Wesdemiotis, J. Am. Soc. Mass Spectrom. 1999, 10, 1241.
26. 2 are peak widths of the parent and one of the daughter ions.
27. a) G. Bojesen, P. Hvelplund, T. J. D. Jørgensen, S. B. Nielsen, J. Chem. Phys. 2000, 113, 6608;
28. b) C. J. Thompson, J. Husband, F. Aguirre, R. B. Metz, J. Phys. Chem. A 2000, 104, 8155.
29. R. Flammang, L. Gallez, Y. V. Haverbeke, M. W. Wong, C. Wentrup, Rapid Commun. Mass Spectrom. 1996, 10, 232.
30. C. Aubry, J. Holmes, J. Am. Soc. Mass Spectrom. 2000, 12, 23.
31. a) K. Lammertsma, P. v. R. Schleyer, H. Schwarz, Angew. Chem. 1989, 101, 1313;
32. Angew. Chem. Int. Ed. Engl. 1989, 28, 1321;
33. b) C. Wesdemiotis, F. W. McLafferty, Chem. Rev. 1987, 87, 485;
34. c) N. Goldberg, H. Schwarz, Acc. Chem. Res. 1994, 27, 347.
35. B. A. Budnik, R. A. Zubarev, Chem. Phys. Lett. 2000, 316, 19.
36. P. Hvelplund, T. J. D. Jørgensen, S. B. Nielsen, M. Sørensen, J. U. Anderson, J. Am. Soc. Mass Spectrom. 2001, 12, 889.
37. In a recent review, Hoaglund-Hyzer et al. (ref. [1b], p. 3044) discuss the site of protonation. See references therein.
38. NIST Chemistry WebBook (Ed.: P. J. Linstrom), NIST Standard Reference Database Number 69, February 2000 Release (htlp:// webbook.nist.gov/chemistry).
39. -, since there is good evidence in the literature that protonated amino acids do not adopt this structure [R. A. Jockusch, W. D. Price, E. R. Williams, J. Phys. Chem. A 1999, 103, 9266].
40. 4 (cf. Table 1).
41. a) L.-S. Wang, X.-B. Wang, J. Phys. Chem. A 2000, 104, 1978;
42. b) S. Gronert, Int. J. Mass Spectrom. 1999, 185, 351;
43. c) S. Gronert, J. Mass Spectrom. 1999, 34, 787.
44. M. B. Nielsen, T. J. D. Jørgensen, P. Hvelplund, S. B. Nielsen, unpublished results.
45. a) D. S. Gross, S. E. Rodriguez-Cruz, S. Bock, E. R. Williams, J. Phys. Chem. 1995, 99, 4034;
46. b) D. S. Gross, E. R. Williams, J. Am. Chem. Soc. 1995, 117, 883;
47. c) P. D. Schnier, D. S. Gross, E. R. Williams, J. Am. Chem. Soc. 1995, 117, 6747.
48. K. L. Stevenson, G. A. Papadantonakis, P. R. LeBreton, J. Photochem. Photobiol. A: Chem. 2000, 133, 159 and references therein.
49. +-Ala is approximately 1 eV independent of the amino acid [W. D. Price, P. D. Schnier, E. R. Williams, J. Phys. Chem. B 1997, 101, 664].
50. + ionization involves the phenol group; for Tyr it requires 0.6 eV more to remove an electron from the nitrogen lone pair than from the phenol side chain: IE(Tyr)=8.0 eV and IE(Tyr, nitrogen lone pair) = 8.6 eV [S. Campbell, J. L. Beauchamp, M. Rempe, D. L. Lichtenberger, Int. J. Mass Spectrom. Ion Processes 1992, 117, 83].
51. V. Q. Nguyen, F. Tureček, J. Mass Spectrom. 1996, 31, 843.
52. a) R. A. Zubarev, N. A. Kruger, E. K. Fridriksson, M. A. Lewis, D. M. Horn, B. K. Carpenter, F. W. McLafferty, J. Am. Chem. Soc. 1999, 121, 2857;
53. b) R. A. Zubarev, D. M. Horn, E. J. Fridriksson, N. L. Kelleher, N. A. Kruger, M. A. Lewis, B. K. Carpenter, F. W. McLafferty, Anal. Chem. 2000, 72, 563.
54. M. Eckert-Maksić, M. Klessinger, Z. B. Maksić, Chem. Phys. Lett. 1995, 232, 472.
55. P. E. M. Siegbahn, M. R. A. Blomberg, R. H. Crabtree, Theor. Chem. Acc. 1997, 97, 289.
56. [32] have calculated the barrier heights for several different hydrogen transfer reactions. B3LYP calculations on the hydrogen transfer between neutral amino acids where a radical group is present indicate that the barrier is low (ca. 0.1 eV) for an exothermic reaction. For the endothermic hydrogen abstraction from methane by the peroxide radical, the barrier height is nearly equal to the reaction energy.
57. a) O. V. Boltalina, P. Hvelplund, T. J. D. Jørgensen, M. C. Larsen, M. O. Larsson, D. A. Sharoitchenko, Phys. Rev. A 2000, 62, 023202;
58. b) M. O. Larsson, P. Hvelplund, M. C. Larsen, H. Shen, H. Cederquist, H. T. Schmidt, Int. J. Mass Spectrom. Ion Processes 1998, 177, 51.
59. Gaussian 95, Revision A.7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.