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DFT ab initio calculations of 22 free radical derived nucleosides analogs were performed in gas phase and water solution. Most of studied compounds exist mainly in expected amino- and keto- forms. However, there were found few important exceptions: enol-amino tautomer of 2-OH-adenosine is dominant in apolar environment, while in polar solution keto-amino isomer become more probable; 8-oxo-guanosine is to be represented as a mixture of two tautomers: 6,8-diketo and 6-enol-8-keto with disfavoring of the latter in polar conditions, 5-OH-cytidine adopts imino-keto form in non-polar surroundings but water stabilizes amino-keto isomer reverting order of these tautomers, cytidine glycol in apolar and polar conditions is represented mainly by keto-imino form, but more polar environment increase percentage of amino-keto tautomer not reverting their order, 6-hydroxy-5,6-dihydroxycytidine in both polar and non-polar conditions adopts keto-imino form, which dominates over keto-amino one, 5-hydroxy-5,6-dihydro-cytosine in non-polar conditions exists as keto-imino tautomer while polar conditions favors keto-amino form.

An ab initio DFT Characteristics of Tautomeric Properties of Hydroxyl Radical Modified Nucleosides in Polar and Non-Polar Environments