Biopolym. Cell. 1997; 13(3):185-190.
http://dx.doi.org/10.7124/bc.00047C
Structure and Function of Biopolymers
To the question of tautomerism of nucleic acid bases
1Boldeskul A. I., 1Sukhodub L. F.
  1. Institute of Applied Physics, NAS of Ukraine
    58, Petropavlivska Str., Sumy, Ukraine, 40030

Abstract

The tautomerism of nucleic acids bases was investigated by semi-empirical method MNDO/H with optimization of all structural parameters. Utilization of MNDO method in similar investigations is fully justified, since the obtained calculated data are in good agreement with the experimental ones. Besides «classical» keto-amine tautomcric forms of the bases, there is the possibility of realization of isolated and paired liquid enole or imine forms in gaseous phase. Enole tautomer of guanine, for example, appeared 7.2 kcal/mol more preferable that keto-amine form, and O(4) enole tautomer of thy mine is 0.6 kcal/mol more preferable than dike-toform. The conclusion was drawn on the bases of proton-acceptor ability of nitrous bases that for the molecules of nitrous bases there is t/ie preference of thermodynamic control over the protonation of nucteophilic centres represented by O(2) cytozine, O(4) thymine, N(l), N(3) adenine and N(7) guanine
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