Substituted adenine quartets: interplay between substituent effect, hydrogen bonding, and aromaticity.

ABSTRACT: Adenine, one of the components of DNA/RNA helices, has the ability to form self-organizing structures with cyclic hydrogen bonds (A₄), similar to guanine quartets. Here, we report a computational investigation of the effect of substituents (X = NO₂, Cl, F, H, Me, and NH₂) on the electronic structure of 9H-adenine and its quartets (A₄-N1, A₄-N3, and A₄-N7). DFT calculations were used to show the relationships between the electronic nature of the substituents, strength of H-bonds in the quartets, and aromaticity of five- and six-membered rings of adenine. We demonstrated how the remote substituent X modifies the proton-donating properties of the NH₂ group involved in the H-bonds within quartets and how the po

SUBMITTER: Szatylowicz H 

PROVIDER: S-EPMC9054646 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature