Formation of 8‐nitroguanine and 8‐oxoguanine due to reactions of peroxynitrite with guanine

Reactions of peroxynitrite with guanine were investigated using density functional theory (B3LYP) employing 6‐31G** and AUG‐cc‐pVDZ basis sets. Single point energy calculations were performed at the MP2/AUG‐cc‐pVDZ level. Genuineness of the calculated transition states (TS) was tested by visually examining the vibrational modes corresponding to the imaginary vibrational frequencies and applying the criterion that the TS properly connected the reactant and product complexes (PC). Genuineness of all the calculated TS was further ensured by intrinsic reaction coordinate (IRC) calculations. Effects of aqueous media were investigated by solvating all the species involved in the reactions using the polarizable continuum model (PCM). The calculations reveal that the most stable nitro‐product complex involving the anion of 8‐nitroguanine and a water molecule i.e. 8NO2G− + H2O can be formed according to one reaction mechanism while there are two possible reaction mechanisms for the formation of the oxo‐product complex involving 8‐oxoguanine and anion of the NO2 group i.e. 8OG + NO2−. The calculated relative stabilities of the PC, barrier energies of the reactions and the corresponding enthalpy changes suggest that formation of the complex 8OG + NO2− would be somewhat preferred over that of the complex 8NO2G− + H2O. The possible biological implications of this result are discussed. © 2007 Wiley Periodicals, Inc. J Comput Chem 2007

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