Gas-Phase Interactions Between Lead(II) Ions and Thiouracil Nucleobases: A Combined Experimental and Theoretical Study

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 3, 2009, Pages 359-369

  Salpin, Jean Yves ^a   Guillaumont, Sébastien ^a   Tortajada, Jeanine ^a   Lamsabhi, Al Mokhtar ^b  

^a UNIVERSITÉ D EVRY VAL D ESSONNE   (France)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 THIOURACILS; CATIONIZATION; COMPLEXATION SITES; COVALENT CHARACTERS; DIFFERENT STRUCTURES; FRAGMENT IONS; FRAGMENTATION CHANNELS; GAS-PHASE; LEAD-IONS; MS/MS EXPERIMENTS; NATURAL POPULATION ANALYSIS; NUCLEOBASES; STABLE STRUCTURES; THEORETICAL CALCULATIONS; THEORETICAL STUDIES;

CHARGE TRANSFER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE; IONS; ISOMERS; MASS SPECTROMETRY; OXYGEN;

SULFUR;

CATIONS; LEAD; MODELS, CHEMICAL; MODELS, MOLECULAR; OXIDATION-REDUCTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFUR; TANDEM MASS SPECTROMETRY; THERMODYNAMICS; THIOURACIL;

EID: 60649116052     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.10.015     Document Type: Article

References (45)

1. Farkas W.R. Depolymerization of Ribonucleic Acid by Plumbous Ion. Biochim. Biophys. Acta 155 (1968) 401-409
2. Phe-Implications for Lead Toxicity and Self-Splicing RNA. Nature 303 (1983) 543-546
3. Brown R.S., Dewan J.C., and Klug A. Crystallographic and Biochemical Investigation of the Lead(II)-Catalyzed Hydrolysis of Yeast Phenylalanine tRNA. Biochemistry 24 (1985) 4785-4801
4. Scott W.G. RNA Structure, Metal Ions, and Catalysis. Curr. Opin. Chem. Biol. 3 (1999) 705-709
5. Guillaumont S., Tortajada J., Salpin J.Y., and Lamsabhi A.M. Experimental and Computational Study of the Gas-Phase Interactions Between Lead(II) Ions and Two Pyrimidic Nucleobases: Uracil and Thymine. Int. J. Mass Spectrom. 243 (2005) 279-293
6. Gutle C., Salpin J.Y., Cartailler T., Tortajada J., and Gaigeot M.P. Proton Transfers Induced by Lead(II) in a Uracil Nucleobase: A Study Based on Quantum Chemistry Calculations. J. Phys. Chem. A 110 (2006) 11684-11694
7. Lehninger A.L. Biochemistry: The Molecular Basis of Cell Structure and Function. 2nd eds. (1975), Worth Publishers, New York
8. Saenger W. Advanced Texts in Chemistry, Principles of Nucleic Acid Structure, (1984), Springer-Verlag, New York
9. Lamsabhi M., Alcamí M., Mó O., Bouab W., Esseffar M., Abboud J.L.M., and Yáñez M. Are the Thiouracils Sulfur Bases in the Gas Phase?. J. Phys. Chem. A 104 (2000) 5122-5130
10. + Cation: A DFT Study. Chem. Phys. Chem. 4 (2003) 1011-1016
11. 2+ with Uracil and Its Thio Derivatives: A Theoretical Study. Chem. Phys. Chem. 5 (2004) 1871-1878
12. 2+ Complexes. J. Phys. Chem. A 110 (2006) 1943-1950
13. 2+ Complexes in the Gas Phase. Chem. Phys. Chem. 8 (2007) 181-187
14. 2+ with Uracil and Its Thio Derivatives in the Gas Phase. Org. Biomol. Chem. 6 (2008) 3695-3702
15. Yang Z.B., and Rodgers M.T. Influence of Thioketo Substitution on the Properties of Uracil and Its Noncovalent Interactions with Alkali Metal Ions: Threshold Collision-Induced Dissociation and Theoretical Studies. J. Phys. Chem. A 110 (2006) 1455-1468
16. Jayaweera P., Blades A.T., Ikonomou M.G., and Kebarle P. Production and Study in the Gas-Phase of Multiply Charged Solvated or Coordinated Metal-Ions. J. Am. Chem. Soc. 112 (1990) 2452-2454
17. Chernushevich I.V., Loboda A.V., and Thomson B.A. An Introduction to Quadrupole-Time-of-Flight Mass Spectrometry. J. Mass Spectrom. 36 (2001) 849-865
18. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., 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., Scalmi 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., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin J., Cammi R., Pomelli C., Ochterski J., 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. Gaussian03, Rev. C.02 (2003), Gaussian, Inc, Wallingford, CT
19. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 37 (1988) 785-789
20. Becke A.D. Density-Functional Thermochemistry. 3. The Role of Exact Exchange. J. Chem. Phys. 98 (1993) 5648-5652
21. Gill P.M.W. A New Gradient-Corrected Exchange Functional. Mol. Phys. 89 (1996) 433-445
22. Küchle W., Dolg M., Stoll H., and Preuss H. Ab Initio Pseudopotentials for Hg Through Rn. I. Parameter Sets and Atomic Calculations. Mol. Phys. 6 (1991) 1945-1963
23. Salpin J.Y., Tortajada J., Alcamí M., Mó O., and Yáñez M. Optimization of Extended Basis Sets and Assessment of Different Theoretical Schemes for Pb Containing Compounds. Chem. Phys. Lett. 383 (2004) 561-565
24. +. Chem. Phys. Lett. 280 (1997) 266-272
25. +(H-2) (n) Clusters: An Experimental and Theoretical Investigation. J. Am. Chem. Soc. 120 (1998) 13494-13502
26. + in the Gas Phase. J. Phys. Chem. A 106 (2002) 2641-2651
27. 2O Complexes as Prototypes of Multiple Hydrogen Bond Systems. J. Comput. Chem. 18 (1997) 1124-1135
28. González L., Mó O., and Yáñez M. High-Level Ab Initio Calculations on the Intramolecular Hydrogen Bond in Thiomalonaldehyde. J. Phys. Chem. A 101 (1997) 9710-9719
29. González L., Mó O., and Yáñez M. High Level Ab Initio and Density Functional Theory Studies on Methanol-Water Dimers and Cyclic Methanol(Water)(2) Trimer. J. Chem. Phys. 109 (1998) 139-150
30. Glendening, E. D.; Reed, A. E.; Weinhold, F. NBO version 3.1.
31. In: Bader R.F.W. (Ed). International Series of Monographs on Chemistry; 22, Atoms in Molecules: A Quantum Theory (1990), Clarendon Press/Oxford University Press, Oxford, New York
32. Matta C.F., and Boyd R.H. The Quantum Theory of Atoms in Molecules (2007), Wiley-VCH, Weinheim
33. Rodgers M.T., and Armentrout P.B. Noncovalent Interactions of Nucleic Acid Bases (Uracil, Thymine, and Adenine) with Alkali Metal Ions. Threshold Collision-Induced Dissociation and Theoretical Studies. J. Am. Chem. Soc. 122 (2000) 8548-8558
34. Katritzky A.R., Baykut G., Rachwal S., Szafran M., Caster K.C., and Eyler J. The Tautomeric Equilibria of Thio Analogs of Nucleic-Acid Bases. 1. 2-Thiouracil-Background, Preparation of Model Compounds, and Gas-Phase Proton Affinities. J. Chem. Soc. Perkin Trans. 2 (1989) 1499-1506
35. Katritzky A.R., Szafran M., and Stevens J. The Tautomeric Equilibria of Thio Analogs of Nucleic-Acid Bases. 2. AM1 and Ab Initio Calculations of 2-Thiouracil and Its Methyl-Derivatives. J. Chem. Soc. Perkin Trans. 2 (1989) 1507-1511
36. Katritzky A.R., Szafran M., and Pfister-Guillouzo G. The Tautomeric Equilibria of Thio Analogs of Nucleic-Acid Bases. 3. Ultraviolet Photoelectron-Spectra of 2-Thiouracil and Its Methyl-Derivatives. J. Chem. Soc. Perkin Trans. 2 (1990) 871-876
37. Leszczynski J., and Lammertsma K. 2,4-Dithiouracil Tautomers: Structures and Energies. J. Phys. Chem. 95 (1991) 3128-3132
38. Leszczynski J., and Sponer J. 2,4-Diselenouracil Tautomers: Structures, Energies, and a Comparison with Uracil and 2,4-Dithiouracil. J. Mol. Struct. Theochem. 388 (1996) 237-243
39. Vaquero V., Sanz M.E., Lopez J.C., and Alonso J.L. The Structure of Uracil: A Laser Ablation Rotational Study. J. Phys. Chem. A 111 (2007) 3443-3445
40. Kurinovich M.A., Phillips L.M., Sharma S., and Lee J.K. The Gas Phase Proton Affinity of Uracil: Measuring Multiple Basic Sites and Implications for the Enzyme Mechanism of Orotidine 5′-Monophosphate Decarboxylase. Chem. Commun. (2002) 2354-2355
41. Zhu W.L., Luo X.M., Puah C.M., Tan X.J., Shen J.H., Gu J.D., Chen K.X., and Jiang H.L. The Multiplicity, Strength, and Nature of the Interaction of Nucleobases with Alkaline and Alkaline Earth Metal Cations: A Density Functional Theory Investigation. J. Phys. Chem. A 108 (2004) 4008-4018
42. Wolken J.K., and Turecek F. Proton affinity of uracil. A Computational Study of Protonation Sites. J. Am. Soc. Mass Spectrom. 11 (2000) 1065-1071
43. Salpin J.Y., Guillaumont S., Tortajada J., MacAleese L., Lemaire J., and Maitre P. Infrared Spectra of Protonated Uracil, Thymine, and Cytosine. Chem. Phys. Chem. 8 (2007) 2235-2244
44. Shimoni-Livny L., Glusker J.P., and Bock W. Lone Pair Functionality in Divalent Lead compounds. Inorg. Chem. 37 (1998) 1853-1867
45. Salpin J.Y., and Tortajada J. Gas-Phase Reactivity of Lead(II) Ions with D-Glucose. Combined Electrospray Ionization Mass Spectrometry and Theoretical Study. J. Phys. Chem. A 107 (2003) 2943-2953