Issue 7, 2019

Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing

Abstract

Density functional theory computations and block-localized wavefunction analyses for 57 hydrogen-bonded base pairs document excellent linear correlation between the gas-phase association energies and the degree of aromaticity gain of paired bases (r = 0.949), challenging prevailing views of factors that underlie the proposed electronic complementarity of A·T(U) and G·C base pairs. Base pairing interactions can polarize the π-electrons of interacting bases to increase (or decrease) cyclic 4n + 2π electron delocalization, resulting in aromaticity gain (or loss) in the paired bases, and become strengthened (or weakened). The potential implications of this reciprocal relationship for improving nucleic acid force-fields and for designing robust unnatural base pairs are discussed.

Graphical abstract: Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing

Supplementary files

Article information

Article type
Paper
Submitted
13 июл 2018
Accepted
22 авг 2018
First published
22 авг 2018

Org. Biomol. Chem., 2019,17, 1881-1885

Author version available

Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing

Y. Zhang, C. Wu and J. I. Wu, Org. Biomol. Chem., 2019, 17, 1881 DOI: 10.1039/C8OB01669K

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