Prototropic tautomerism of 9-methylguanine: quantum-mechanical investigation

1Glushenkov, AN, 1Hovorun, DM
1Institute of High Technology, Taras Shevchenko National University of Kyiv; Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv
Dopov. Nac. akad. nauk Ukr. 2014, 9:151-156
https://doi.org/10.15407/dopovidi2014.09.151
Section: Biophysics
Language: Russian
Abstract: 

For the first time, the full molecular-zwitterionic 9-methylguanine family has been obtained in vacuum, water, DMSO, and the ε = 4 continuum. It is shown that it consists of 14 molecular tautomers and 18 zwitterions, 9 of which are ylides.

Keywords: 9-methylguanine, prototropic tautomerism
References: 

1. Watson J. D., Crick F. H. C. Nature, 1953, 171: 964–967. https://doi.org/10.1038/171964b0
2. Service R. F. Science, 2011, 332: 1140. https://doi.org/10.1126/science.332.6034.1140
3. Benenson Y. Mol. Biosyst., 2009, 5: 675. https://doi.org/10.1039/b902484k
4. Li D., Fan C. DNA nanotechnology. From structure to function, Springer, 2013.
5. Zhu C., Wen Y., Peng H., et al. Anal. Bioanal. Chem., 2011, 399: 3459–3464. https://doi.org/10.1007/s00216-010-4137-2
6. Geunjung L., Young-Gui Y. J. of the Korean Physical Society., 2012, 60: 1452–1456. https://doi.org/10.3938/jkps.60.1452
7. Pullman B., Pullman A. Advances in Heterocyclic Chemistry, 1971, 13: 77–159. https://doi.org/10.1016/S0065-2725(08)60349-9
8. Szczepaniak K., Szczesniak M. J. Mol. Struct., 1987, 156: 29–42. https://doi.org/10.1016/0022-2860(87)85038-X
9. Sheina G. G., Stepanian S. G., Radchenko E. D. J. Mol. Struct., 1987, 158:  275–292. https://doi.org/10.1016/0022-2860(87)80024-8
10. Sabio M., Topiol S., Lumma W. C., Jr. J. Phys. Chem., 1990, 94: 1366–1372. https://doi.org/10.1021/j100367a032
11. Wanchun L., Haoran L., Xingbang H., Shijun H. Chem. Phys., 2006, 328: 93–102. https://doi.org/10.1016/j.chemphys.2006.06.025
12. Plekan O., Feyer V. et al. J. Phys. Chem., A – 2009, 113: 9376–9385. https://doi.org/10.1021/jp903209t
13. Brovarets’O. O., Hovorun D. M. J. of Biomol. Structure and Dynamics, 2012: 1–24.
14. Tomasi J., Mennucci B., Cammi R. Chem. Rev., 2005, 105: 2999–3093. https://doi.org/10.1021/cr9904009