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Natural nucleic acid bases can form Watson-Crick (WC) or Hoogsteen (HG) base pairs. Importantly, 8-oxo-2'-deoxyguanosine (8-oxo-dG) in DNA or 8-oxo-dG 5'-triphosphate (8-oxo-dGTP) favors a syn conformation because of the steric repulsion between O8 and O4' of the deoxyribose ring. 8-oxo-dGTP can be incorporated into DNA opposite the templating adenine (A) using HG pairing as the dominant mechanism. Both RNA and DNA can be methylated at the N6 position of A to form N  6 -methyladenine (m 6 A). It has been found that certain viral infections may trigger an increase in the production of both 8-oxo-dGTP and m 6 A. The current study aims to systematically explore the effects of m 6 A methylation on HG base pairs and the consequent nucleotide incorporation. Our thermodynamic melting study shows that the m 6 A·8-oxo-dG is significantly less stable than the A·8-oxo-dG base pair in the paired region of a DNA duplex. Moreover, we have used pre-steady-state kinetics to examine the incorporation of 8-oxo-dGTP opposite m 6 A relative to A by a variety of reverse transcriptase (RT) enzymes and DNA polymerase (DNA pol) enzymes such as the human immunodeficiency virus type 1 (HIV-1) RT and human DNA pol β. The results demonstrate that all of these enzymes incorporate 8-oxo-dGTP less efficiently opposite m 6 A relative to A. Considering the steric bulk of the purine-purine pair between 8-oxo-dG and A, m 6 A methylation may affect the HG pairing to a great extent. Hence, it will be unfavorable to incorporate 8-oxo-dGTP into the growing strand opposite m 6 A. Moreover, the impeded incorporation of 8-oxo-dGTP opposite m 6 A has been extended to determine m 6 A at pre-defined positions in human rRNA. Our study may provide new insights into the roles of m 6 A in reducing the mutagenic potential of cellular 8-oxo-dGTP.

The m6A methylation perturbs the Hoogsteen pairing-guided incorporation of an oxidized nucleotide

The m⁶A methylation perturbs the Hoogsteen pairing-guided incorporation of an oxidized nucleotide