Infrared multiple photon dissociation action spectroscopy of protonated uracil and thiouracils: Effects of thioketo-substitution on gas-phase conformation

International Journal of Mass Spectrometry

Volumn 297, Issue 1-3, 2010, Pages 139-151

  Nei, Y W ^a   Akinyemi, T E ^a   Steill, J D ^b   Oomens, J ^b,c   Rodgers, M T ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Free electron laser; Infrared multiple photon dissociation; Proton; Thiouracil; Uracil

Indexed keywords

EID: 78049305103     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2010.08.005     Document Type: Article

References (69)

1. Watson J.D., Crick F.H. Nature 1953, 171:964.
2. Löwdin P.-O. Rev. Mod. Phys. 1963, 35:724.
3. Topal M.D., Fresco J.R. Nature 1976, 263:285.
4. Ts'o P.O.P. Basic Principles in Nucleic Acids Chemistry 1974, Academic, New York.
5. Rüterjans H., Kaun E., Hull W.E., Limbach H.H. Nucleic Acid Res. 1982, 10:7.
6. Dougherty D., Wittel K., Meeks J., McGlynn S.P. J. Am. Chem. Soc. 1976, 98:3815.
7. Tsuchiya Y., Fujii M., Ito M. J. Phys. Chem. 1988, 92:1760.
8. Brady B.B., Peteanu L.A., Levy D.H. Chem. Phys. Lett. 1988, 147:538.
9. Shugar D., Szczepaniak K. Int. J. Quantum Chem. 1981, 20:573.
10. Szczesniak M., Nowak M.J., Szczepaniak K., Person W.B., Shugar D. J. Am. Chem. Soc. 1983, 105:5969.
11. Chin S., Scott I., Szczepani K., Person W.B. J. Am. Chem. Soc. 1984, 106:3415.
12. Brown R.D., Godfrey P.D., McNaughton D., Pierlot A.P. J. Am. Chem. Soc. 1988, 110:2329.
13. Beak P., White J.M. J. Am. Chem. Soc. 1982, 104:7073.
14. Kwiatkowski J.S., Zielinski T.J., Rein R. Adv. Quantum Chem. 1986, 18:85.
15. Czerminski R., Lesying B., Pohorille A. Int. J. Quantum Chem. 1979, 16:605.
16. Scanlan M.J., Hillier I.H. J. Am. Chem. Soc. 1984, 106:3737.
17. Norinder U. THEOCHEM 1987, 36:259.
18. Gould I.R., Hiller I.H. J. Chem. Soc. Perkin Trans. 1990, 2:329.
19. Gould I.R., Burton N.A., Hall R.J., Hiller I.H. THEOCHEM 1995, 331:147.
20. Leszczynski J. J. Phys. Chem. 1992, 96:1649.
21. Leś A., Adamowicz L. J. Phys. Chem. 1989, 93:7078.
22. Estrin D.A., Paglieri L., Corongiu G. J. Phys. Chem. 1994, 98:5653.
23. Tian S.X., Zhang C.F., Zhang Z.J., Chen X.J., Xu K.Z. Chem. Phys. 1999, 242:217.
24. Paglieri L., Corongiu G., Estrin D.A. Int. J. Quantum Chem. 1995, 56:615.
25. Hunter E.P., Lias S.G. Evaluated gas-phase basicities and proton affinities of molecules: an update. J. Phys. Chem. Ref. Data 1998, 27:413.
26. Kurinovich M.A., Phillips L.M., Sharma S., Lee J.K. Chem. Commun. 2002, 20:2354.
27. Wu R., McMahon T.B. J. Am. Chem. Soc. 2007, 129:569.
28. Wolken J.K., Tureček F. J. Am. Soc. Mass Spectrom. 2000, 11:1065.
29. Kryachko E.S., Nguyen M.T., Zeegers-Huyskens T. J. Phys. Chem. A 2001, 105:1288.
30. Nguyen M.T., Chandra A.K., Zeegers-Huyskens T. J. Chem. Soc. Faraday Trans. 1998, 94:1277.
31. Podolyan Y., Gorb L., Leszczynski J. J. Phys. Chem. A 2000, 104:7346.
32. Salpin J.-Y., Guillamont S., Tortajada J., MacAleese L., Lemaire J., Maitre P. Chem. Phys. Chem. 2007, 8:2235.
33. Bakker J.M., Sinha R.K., Besson T., Brugnara M., Tosi P., Salpin J.-Y., Maitre P. J. Phys. Chem. A 2008, 112:12393.
34. Saenger W. Principles of Nucleic Acid Structure 1984, Springer-Verlag, New York, Berlin, Heidelberg, Tokyo, Chapter 7.
35. Yaniv M., Folk W.R. J. Biochem. 1975, 250:3243.
36. Jeffrey G.A., Saenger W. Hydrogen Bonding in Biological Structures 1991, Springer, New York.
37. Beck C.F., Howlett G. J. Mol. Biol. 1977, 111:1.
38. Miller W.H., Robin R.O., Astwood E.B. J. Am. Chem. Soc. 1945, 67:2201.
39. Williams R.H., Bissell G.W. Science 1943, 98:156.
40. Ortiga-Carvalho T.M., Hashimoto K., Pazos-Moura C.C., Greenen D., Cohen R., Lang R.M., Wondisford F.E. Endocrinology 2004, 145:1625.
41. Gredilla R., Barja G., Lopez-Torres M. Free Radical Res. 2001, 35:417.
42. Palumbo A., d'Ishia M. Biochem. Biophys. Res. Commun. 2001, 282:793.
43. Sulkowska A., Równicka J., Bojko B., Sulkowski W. J. Mol. Struct. 2003, 651:133.
44. Theodossiou C., Schwarzenberger P. Am. J. Med. Sci. 2000, 319:96.
45. Macchia M., Barontini S., Bertini S., Di Bussolo V., Forli S., Giovannetti E., Grossi E., Minutolo F., Danesi R. J. Med. Chem. 2001, 44:3994.
46. Elias A.N. Med. Hypotheses 2004, 62:431.
47. Antoniadis C.D., Corban G.J., Hadjikakou S.K., Hadjiliadis N., Kubicki M., Warner S., Butler I.S. Eur. J. Inorg. Chem. 2003, 8:1635.
48. Imam D.R., El-barbary A.A., Nielsen C., Pedersen E.B. Monatsh. Chem. 2002, 133:723.
49. Abdel-Rahman A.A.H., Abdel-Megied A.E.S., Goda A.E.S., Zeid I.F., El Ashry E.S.H. Nucleos. Nucleot. 2003, 22:2027.
50. Inazumi M., Kano F., Sakata S. Chem. Pharm. Bull. 1992, 40:1808.
51. Castillo J., Benavente-Garcia O., Lorente J., Alcaraz M.J., Redondo A., Ortuno A., Del Rio J.A. J. Agric. Food Chem. 2000, 48:1738.
52. Rostkowska H., Barski A., Szczepaniak K., Szczesniak M., Person W.B. J. Mol. Struct. 1988, 176:137.
53. Rostkowska H., Szczepaniak K., Nowak M.J., Leszczynski J., KuBulat K., Person W.B. J. Am. Chem. Soc. 1990, 112:2147.
54. Graindourze M., Grootaers T., Smets J., Zeegers-Huyskens T., Maes G. J. Mol. Struct. 1990, 237:389.
55. Lapinski L., Rostkowska H., Nowak M.J., Kwiatkowski J.S., Leszczynski J. Vib. Spectrosc. 1996, 13:23.
56. Katritzky A.R., Baykut G., Rachwal S., Szafran M., Caster K.C., Eyler J. J. Chem. Soc. Perkin Trans. 1989, 2:1499.
57. Katritzky A.R., Szafran M., Stevens J. J. Chem. Soc. Perkin Trans. 1989, 2:2194.
58. Leś A., Adamowicz L.J. J. Am. Chem. Soc. 1990, 112:1504.
59. Rubin Y.V., Morozov Y., Venkateswarlu D., Leszczynski J. J. Phys. Chem. A 1998, 102:2194.
60. Lamsabhi M., Alcamí M., Mó O., Bouab W., Esseffar M., Abboud J.L.-M., Yáñez M. J. Phys. Chem. A 2000, 104:5122.
61. Valle J.J., Eyler J.R., Oomens J., Moore D.T., van der Meer A.F.G., von Heldon G., Meijer G., Hendrickson C.L., Marshall A.G., Blakney G.T. Rev. Sci. Instrum. 2005, 76:023103.
62. Polfer N.C., Oomens J., Moore D.T., von Helden G., Meijer G., Dunbar R.C. J. Am. Chem. Soc. 2006, 128:517.
63. Polfer N.C., Oomens J. Phys. Chem. Chem. Phys. 2007, 9:3804.
64. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery 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., 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., Pople J.A. Gaussian 03, Revision D.01 2005, Gaussian, Inc., Pittsburgh, PA.
65. Foresman J.B., Frisch A.E. Exploring Chemistry with Electronic Structure Methods 1996, Gaussian, Pittsburgh, PA, p. 64. 2nd ed.
66. Yang Z., Rodgers M.T. J. Phys. Chem. A 2006, 110:1455.
67. Kryachko E., Nguyen M.T., Zeegers-Huyskens T. J. Phys. Chem. A 2001, 105:3379.
68. Peng C.Y., Schlegel H.B. Isr. J. Chem. 1994, 33:449.
69. Oomens J., Sartakov B.G., Meijer G., von Helden G. Int. J. Mass Spectrom. 2006, 254:1.