Abstract
The hydrolytic deamination mechanism of protonated adenine has been studied using density functional theory method. There are five pathways according to adenine protonated at N1, N3 and N7, respectively. As for the N1 protonated adenine only one pathway has been found, while for N3 and N7 protonated adenine two pathways have been found. Pathway c2 is preferred due to lowest activation free energy barrier of 53.02 kcal/mol. In this pathway, the hydroxyl group of water attacks C6 atom and hydrogen atom attacks N10 atom to produce enol form of protonated hypoxanthine and ammonia, then hydrogen transfer occurs to cause enol-keto tautomerization of protonated hypoxanthine with the assistance of ammonia. Adenine deamination is easier to take place under acidic condition than under neutral condition owing to lower activation energy barrier.
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