Biopolym. Cell. 1997; 13(3):191-196.
http://dx.doi.org/10.7124/bc.00047D
Structure and Function of Biopolymers
The prototropic tautomerism of nitrogen bases: a new insight into the old problem
1Hovorun D. M.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

The summary is made of the scries of calculation-theoretical investigations fulfilled by the setniempirical quantum-chemical AMI method on physico-chemical features of prototropic tautomerism of nucleotide bases. Applying of non-traditional approach which is based on the view that highest possible numbers of prototropic tautomers of bases are determined by an overall Quantity of protons and electron lone pairs of proton acceptor atoms, the success was achieved in ascertaining that as regards prototropic tautomerism nudcotule bases are more mobile structures (prototropic tautomerism of nucleotide bases has a molecular-zwitterionic diameter involving carboprotons as well) than it was assumed earlier. A biological significance of the data obtained, which are generalized and may be extended from the autlwr's point of view to larmier range of objects, ammo acids included.
Full text: (PDF, in Ukrainian)

References

[1] Lewin B. Genes. (2nd Edition). New York, John Wiley & Sons, 1985; 734 p.
[2] Poltev VI, Bruskov VI, Shuliupina NV, Rein R, Shibata M, Ornstein R, Miller J. Genotoxic modification of nucleic acid bases and biological consequences of it. Review and prospects of experimental and computational investigations. Mol Biol (Mosk). 1993;27(4):734-57.
[3] Danilov VI, Kventsel' GF. Electronic presentation in theory of point mutations Kiev: Naukova Dumka, 1971; 83 p.
[4] Grebneva EA. Irradiation of DNA with ultraviolet light: potential changes and mutations. Mol Biol (Mosk). 1994;28(4):805-12.
[5] Volkov SN.A cracked state of the double-helical DNA. Mol Biol (Mosk). 1995;29(5):1086-94.
[6] Frank-Kamenetskii MD. Fluctuational mobility of DNA. Mol Biol (Mosk). 1983;17(3):639-52.
[7] Pullman P, Pullman A. Quantum Biochemistry. Wiley, 1965; 654p.
[8] Norinder, U. A theoretical reinvestigation of the nucleic bases adenine, guanine, cytosine, thymine and uracil using AM1. Journal of Molecular Structure: THEOCHEM, 1987; 151 (C):259-269.
[9] Sabio M, Topiol S Lumma Jr WC. An investigation of tautomerism in adenine and guanine. J Phys Chem. 1990; 94 (4):1366-1372.
[10] Kwiatkowski JS, Person WB. The tautomerism of the nucleic acid bases revisited: From non-interacting to interacting basesI Eds D. L. Beveridge, R. Lavery. New York: Adenine press. Theor biochem mol biophys. 1990: 153-171.
[11] Zefirov HS, Trach SS. Rearrangement and cyclization. XV. Tautomerism: common problems, classification, search for new topological and reaction types. Zh Org Khim. 1976; 12(4):697-718.
[12] Sheina GG. Prototropic tautomerism of purine and pyrimidine bases of nucleic acids: Thesis. ... Dr. Khim. nauk. Kiev: Inst bioorg. Chemistry and petrochemistry of Sciences of Ukraine, 1992; 42p
[13] Person, WB, Szczepaniak K, Szczesniak M, Kwiatkowski JS, Hernandez, L., Czerminski, R. Tautomerism of nucleic acid bases and the effect of molecular interactions on tautomeric equilibria. J Mol Struct. 1989; 194 (C):239-58.
[14] Govorun D.M, Kondratyuk IV, Zheltovsky NV. Nucleotide bases as CH-Acids. Biopolym Cell. 1995; 11(5):15-20
[15] Bruskov VI, Okon MS. Thermal characteristics of the C--H...O hydrogen bonds formed by nucleic acid base analogs Dokl Akad Nauk SSSR. 1984;277(6):1482-6
[16] Pogorelyi V K, Vishnyakova T B, The Hydrogen Bond and CH Acidity, RUSS CHEM REV, 1984, 53 (12), 1154–67.
[17] Vishnyakova TV, Pogorelyi VK. Relationships between the proton donor capacity in hydrogen bonds and the CH acidity. Theoretical and Experimental. 1984; 20(1):29-33
[18] Govorun DM, Kondratyuk IV, Zheltovsky NV. Acidic-basic properties of pyrimidine, imidazole and purine in vacuum: calculation by AMI method. Biopolym Cell. 1995; 11(5):21-3.
[19] Govorun DM, Kondratyuk IV, Zheltovsky NV. Acidic-basic properties of molecular hypoxanthine in vacuum. Biopolym Cell. 1995; 11(1):36-9.
[20] Govorun DM, Kondratyuk IV, Zheltovsky NV. Acidic-basic properties of molecular xanthine and its complex formation ability. Biopolym Cell. 1994; 10(6):61-4.
[21] Hovorun DM, Kondratyuk IV. Gas-phase acid-alkaline properties of canonical nucleotide bases. Dopovidi Nats Akad Nauk Ukrainy. 1998; (1):207-12.
[22] Hovorun DM, Mishchuk YaR, Kondratyuk IV. On a quantum-chemical nature of a stereochemical nonrigidity of canonical nucleotide bases. Biopolym Cell. 1996; 12(5):5-12
[23] Mahler HR, Cordes EH. Basis of Biological Chemistry. Russ edition, M Mir. 568 p.
[24] Hovorun DM. Structural-energetic peculiarities of spontaneous examination of canonical nucleotide bases and their modified analogues. Biopolym Cell. 1997; 13(1):36-8.
[25] Hovorun DM. The damage of purine bases by oxygen radicals: energetic and structural aspects. Biopolym Cell. 1997;13(6):442-4.
[26] Kondratyuk IV, Govorun DM, Zheltovsky NV. Prototropic molecular-zwitterion tautomerism of xanthine: AMI calculation. Biopolym. Cell. 1994; 10(6):52-60.
[27] Govorun DM, Kondratyuk IV, Zheltovsky NV. Prototropic molecular-zwitterion tautomerism of hypoxanthine: AMI calculation in vacuum. Biopolym Cell. 1995; 11(1):30-5.
[28] Kondratyuk IV, Govorun DM, Zheltovskyy MV. Prototropic tautomerism of molecular xanthine. Dopovidi Nats Akad Nauk Ukrainy. 1995; (4):109-12.
[29] Kondratyuk IV, Govorun DM, Zheltovsky M.V. Prototropic molecular-zwitterion tautomerism hypoxanthine. Dopovidi Nats Akad Nauk Ukrainy. 1995; (7):135-8.
[30] Govorun DM, Kondratyuk IV, Zheltovsky NV. Prototropic molecular-zwitterion tautomerism of imidazole and pyrimidine. Biopolym. Cell. 1995; 11(6):41-4.
[31] Govorun DM, Kondratyuk IV, Zheltovsky NV. Prototropic molecular-zwitterion tautomerism of purine. Biopolym Cell. 1995; 11(6):45-50
[32] Govorun DM, Kondratyuk IV. The quantum mechanical calculations evidence molecular-zwitterionic features of prototropfc tautomerism of canonical nucleotide bases. 1. Pyrimidines. Biopolym Cell. 1996; 12(1):42-48
[33] Govorun DM, Kondratyuk IV. The quantum mechanical calculations evidence molecular-zwitterionic features of prototropic tautomerism of canonical nucleotide bases. 2. Purines. Biopolym Cell. 1996; 12(1):49-52
[34] Handbook of biochemistry and molecular biology . Ed. G. D. Fasman Boca Raton: CRC Press, 1983 Vol. II 923 p.
[35] Govorun DM, Kondratyuk IV, Zheltovsky NV. About physical-chemical mechanism of hydrogen-tritium exchange of purine nucleotide bases C8H8 groups with water. Biopolym Cell. 1995; 11(3-4):24-28, 34
[36] Agranovich IM. Conformational features of DNA in solution and in biological objects, revealed by the slow H1-H3 - exchange: Author. dis. ... kand. khim. nauk, Moscow: USSR Academy of Sciences Institute of Molecular Biology, 1985 21 p.
[37] Govorun DM, Kondratyuk IV, Zheltovsky NV. The influence of protonation and deprotonation, on the acidic-basic properties of purine, pyrimidine and imidazole. Biopolym Cell. 1995; 11(3-4):29-34
[38] Mishchuk YaR. Study of physical and chemical nature of the elementary acts of protein-nucleic acid and nucleic-nucleic acid recognition in low-model systems: Author. Thesis. ... Kand biol nauk. Kyiv: IMBG NAS Ukraine, 1993 21 p.
[39] Kondratiuk IV Study of physico-chemical nature of the basic processes of molecular recognition by NMR, vibrational spectroscopy and modeling omp'yuternoho: Author. Thesis. ... Candidate. Biol. of Sciences Kyiv: IMBG NAS Ukraine, 1996 19 p.
[40] Govorun DM, Kondratyuk IV. Anisotropic rotation of amino groups in canonical nucleotide bases. Dopovidi Nats Akad Nauk Ukrainy. 1996;(10):151-4.
[41] Hovorun DM, Mishchuk YaR, Kondratyuk IV. Topological features of potential energy hypersurface of canonical nucleotide bases. Biopolym Cell. 1996; 12(5):13-17
[42] Govorun DM, Kondratyuk IV, Mishchuk YaR, Zheltovskyi MV. The nonequavalence of amine hydrogens in canonical nucleotide bases. Dopovidi Nats Akad Nauk Ukrainy. 1995; (8):130-2.
[43] Govorun DM, Mishchuk YaR, Kondratyuk IV, Zheltovsky MV. Intramolecular cooperative hydrogen bonds in nucleotide bases. Dopovidi Nats Akad Nauk Ukrainy. 1996;(8):141-4.
[44] Kolomiyets' IM. Study of specific interaction of the carboxyl group of amino acids with nucleotide bases, nucleosides and their metylpohidnymy methods of optical spectroscopy: Author. Thesis. ... Kand biol nauk. Kyiv, IMBG NAS of Ukraine, 1996; 21 p.
[45] Hovorun DM, Mishchuk YaR, Kondratyuk IV, Kucher VV. Spetsyfichna vzayemodiya kanonichnykh nukleotydnykh osnov z karboksyl'noyu hrupoyu aminokyslot ta karboksylat-anionom: rozrakhunok metodom MNDO/H u vakuumi. Ukr Biokhim Zh. (in press)
[46] Zorkyy LM, Razumaeva AE. On coexistence in organic crystals of molecules having different structure. Zhurn Strukt Khymii. 1979;20(3):463-6.
[47] Razumayeva AYe, Zorkiy PM. A quantitative comparison of the geometry of organic molecules. Zhurn Strukt Khymii. 1980; 21,(2):77-82.
[48] Urazovsky S. Molecular polymorphism Kiev: Academy of Sciences of the USSR, 1956 336 p.
[49] Gurskaya GV structures of amino acids, Nauka, 1966 160 p.
[50] Kuri AL. Role of solvent in organic reactions. Zhurn. Vsesoyuz. khim. o-va im. D. I. Mendeleyeva. 1984; 29(5): 530—540.
[51] Samoishn VV Zefirov YS Conformational transformations of organic molecules in solutions Zhurn. Vsesoyuz. khim. o-va im. D. I. Mendeleyeva 1984, 29(5):21—530.
[52] Bulgarevich SV, Movshovich DYA. Onsager approximation and universal interaction of polar molecules. Zhurn oObshch Khimii. 1992 62(124), N 10: 2187.
[53] Kizel' VA. Physical causes of asymmetry in living systems. Nauka. 1985. 120 p