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Issue 7, 2019
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Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing

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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

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Article information


Submitted
13 Jul 2018
Accepted
22 Aug 2018
First published
22 Aug 2018

Org. Biomol. Chem., 2019,17, 1881-1885
Article type
Paper
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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