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Tautomerism and Protonation of Guanine and Cytosine. Implications in the Formation of Hydrogen-Bonded Complexes
Abstract
Tautomerism and protonation of guanine and cytosine in the gas phase and in aqueous solution have been examined by theoretical methods. High level ab initio calculations with inclusion of correlation effects at the Møller−Plesset level have been used to study these processes in the gas phase. The influence of solvent has been examined using self-consistent reaction field and Monte Carlo free energy perturbation simulations. The results provide a complete and accurate picture of tautomerism and protonation of these nucleic acid bases. Comparison with the available experimental data gives confidence in the quality of the results derived from theoretical computations. Inspection of the most stable tautomeric forms for the neutral and protonated nucleic acid bases allows rationalization of the formation of unusual DNA structures like the triple helix.
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Cites
Density-functional thermochemistry. III. The role of exact exchange
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464913 · Cited by 103,767
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
Comparison of simple potential functions for simulating liquid water
Jorgensen, W. L., Chandrasekhar, J., Madura, J. D., Impey, R. W., & Klein, M. L. (1983) · The Journal of Chemical Physics · doi:10.1063/1.445869 · Cited by 41,298
Boys, S. F., & Bernardi, F. (1970) · Molecular Physics · doi:10.1080/00268977000101561 · Cited by 22,188
The influence of polarization functions on molecular orbital hydrogenation energies
Hariharan, P. C., & Pople, J. A. (1973) · Theoretica Chimica Acta · doi:10.1007/bf00533485 · Cited by 15,816
Note on an Approximation Treatment for Many-Electron Systems
Møller, C., & Plesset, M. S. (1934) · Physical Review · doi:10.1103/physrev.46.618 · Cited by 14,614
Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic Acid
WATSON, J. D., & CRICK, F. H. C. (1953) · Nature · doi:10.1038/171737a0 · Cited by 13,584
Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., & Stewart, J. J. P. (1985) · Journal of the American Chemical Society · doi:10.1021/ja00299a024 · Cited by 13,074
Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18
McLean, A. D., & Chandler, G. S. (1980) · The Journal of Chemical Physics · doi:10.1063/1.438980 · Cited by 9,798
Miertuš, S., Scrocco, E., & Tomasi, J. (1981) · Chemical Physics · doi:10.1016/0301-0104(81)85090-2 · Cited by 8,937
Principles of Nucleic Acid Structure
Saenger, W. (1984) · Springer Advanced Texts in Chemistry · doi:10.1007/978-1-4612-5190-3 · Cited by 4,150
High-Temperature Equation of State by a Perturbation Method. I. Nonpolar Gases
Zwanzig, R. W. (1954) · The Journal of Chemical Physics · doi:10.1063/1.1740409 · Cited by 3,066
Miertus̃, S., & Tomasi, J. (1982) · Chemical Physics · doi:10.1016/0301-0104(82)85072-6 · Cited by 2,475
Record, M. T., Anderson, C. F., & Lohman, T. M. (1978) · Quarterly Reviews of Biophysics · doi:10.1017/s003358350000202x · Cited by 1,673
Lias, S. G., Liebman, J. F., & Levin, R. D. (1984) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555719 · Cited by 1,324
FORMATION OF A THREE-STRANDED POLYNUCLEOTIDE MOLECULE
Felsenfeld, G., Davies, D. R., & Rich, A. (1957) · Journal of the American Chemical Society · doi:10.1021/ja01565a074 · Cited by 931
Nucleic Acids and Molecular Biology
(1994) · Nucleic Acids and Molecular Biology · doi:10.1007/978-3-642-78666-2 · Cited by 765
(1995) · Choice Reviews Online · doi:10.5860/choice.32-6212 · Cited by 755
Pranata, J., Wierschke, S. G., & Jorgensen, W. L. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00008a002 · Cited by 599
Structures for the polynucleotide complexes poly(dA) · poly(dT) and poly(dT) · poly(dA) · poly(dT)
Arnott, S., & Selsing, E. (1974) · Journal of Molecular Biology · doi:10.1016/0022-2836(74)90498-7 · Cited by 424
DNA H form requires a homopurine–homopyrimidine mirror repeat
Mirkin, S. M., Lyamichev, V. I., Drushlyak, K. N., Dobrynin, V. N., Filippov, S. A., & Frank-Kamenetskii, M. D. (1987) · Nature · doi:10.1038/330495a0 · Cited by 407
Momany, F. A. (1978) · The Journal of Physical Chemistry · doi:10.1021/j100494a019 · Cited by 379
Structures for the polynucleotide complexes Poly(dA)·Poly(dT) and Poly (dT)·Poly(dA)·Poly(dT)
(1975) · Journal of Molecular Biology · doi:10.1016/0022-2836(75)90194-1 · Cited by 367
Experimental studies of molecular interactions between nitrogen bases of nucleic acids
Yanson, I. K., Teplitsky, A. B., & Sukhodub, L. F. (1979) · Biopolymers · doi:10.1002/bip.1979.360180510 · Cited by 338
A Nucleic Acid Triple Helix Formed by a Peptide Nucleic Acid-DNA Complex
Betts, L., Josey, J. A., Veal, J. M., & Jordan, S. R. (1995) · Science · doi:10.1126/science.270.5243.1838 · Cited by 298
Greco, F., Liguori, A., Sindona, G., & Uccella, N. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00181a009 · Cited by 217
Complexes of the Minor Groove of DNA
Geierstanger, B. H., & Wemmer, D. E. (1995) · Annual Review of Biophysics and Biomolecular Structure · doi:10.1146/annurev.bb.24.060195.002335 · Cited by 197
DNA structure and perturbation by drug binding
Neidle, S., Pearl, L. H., & Skelly, J. V. (1987) · Biochemical Journal · doi:10.1042/bj2430001 · Cited by 163
The crystal structure of guanine monohydrate
Thewalt, U., Bugg, C. E., & Marsh, R. E. (1971) · Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry · doi:10.1107/s0567740871005880 · Cited by 158
Matrix isolation studies of cytosine: The separation of the infrared spectra of cytosine tautomers
Nowak, M. J., Lapinski, L., & Fulara, J. (1989) · Spectrochimica Acta Part A: Molecular Spectroscopy · doi:10.1016/0584-8539(89)80129-1 · Cited by 158
Tautomerism in cytosine and 3-methylcytosine. A thermodynamic and kinetic study
Dreyfus, M., Bensaude, O., Dodin, G., & Dubois, J. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00436a045 · Cited by 147
Bachs, M., Luque, F. J., & Orozco, M. (1994) · Journal of Computational Chemistry · doi:10.1002/jcc.540150408 · Cited by 141
Self-citationMatrix isolation infrared studies of nucleic acid constituents
Szczepaniak, K., & Szczesniak, M. (1987) · Journal of Molecular Structure · doi:10.1016/0022-2860(87)85038-x · Cited by 139
Lin, J.-H., Yu, C., Peng, S., Akiyama, I., Li, K., Lee, L. K., & LeBreton, P. R. (1980) · The Journal of Physical Chemistry · doi:10.1021/j100446a015 · Cited by 122
DNA triple-helix specific intercalators as antigene enhancers: Unfused aromatic cations
Wilson, W. D., Tanious, F. A., Mizan, S., Yao, S., Kiselyov, A. S., Zon, G., & Strękowski, L. (1993) · Biochemistry · doi:10.1021/bi00091a011 · Cited by 119
Ionization of bromouracil and fluorouracil stimulates base mispairing frequencies with guanine
Yu, H., Eritja, R., Bloom, L. B., & Goodman, M. F. (1993) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)82342-0 · Cited by 97
Electrostatic Effects in DNA Triple Helixes
Völker, J., & KLUMP, H. H. (1994) · Biochemistry · doi:10.1021/bi00249a039 · Cited by 94
An ab initio quantum-mechanical study of tautomerism of purine, adenine and guanine
Kwiatkowski, J. S., & Leszczyński, J. (1990) · Journal of Molecular Structure THEOCHEM · doi:10.1016/0166-1280(92)80005-7 · Cited by 89
Sowers, L. C., Goodman, M. F., Eritja, R., Kaplan, B., & Fazakerley, G. V. (1989) · Journal of Molecular Biology · doi:10.1016/0022-2836(89)90353-7 · Cited by 72
Leś, A., Adamowicz, L., & Bartlett, R. J. (1989) · The Journal of Physical Chemistry · doi:10.1021/j100347a028 · Cited by 67
Kaito, A., Hatano, M., Ueda, T., & Shibuya, S. (1980) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.53.3073 · Cited by 35
Cited by
Theoretical Methods for the Description of the Solvent Effect in Biomolecular Systems
Orozco, M., & Luque, F. J. (2000) · Chemical Reviews · doi:10.1021/cr990052a · Cited by 622
Self-citationImprota, R., Santoro, F., & Blancafort, L. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00444 · Cited by 499
Metadata
- Authors
- Colominas, C., Luque, F. J., & Orozco, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1996-01-01
- Volume
- 118
- Issue
- 29
- Pages
- 6811-6821
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2009120757
- Cited by
- 332
- References
- 41
- FWCI
- 6.18
- Type
- journal article
- Language
- en
- Open access
- closed
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