Crystallographic evidence of Watson–Crick connectivity in the base pair of anionic adenine with thymine

Mishra, Manish Kumar; Kelley, Steven P.; Smetana, Volodymyr; Dixon, David A.; McNeill, Ashley S.; Mudring, Anja-Verena; Rogers, Robin D.

doi:10.1073/pnas.2008379117

Crystallographic evidence of Watson–Crick connectivity in the base pair of anionic adenine with thymine

Journal Article · Fri Jul 17 00:00:00 EDT 2020 · Proceedings of the National Academy of Sciences of the United States of America

DOI:https://doi.org/10.1073/pnas.2008379117· OSTI ID:1657346

Mishra, Manish Kumar ^[1]; Kelley, Steven P. ^[2]; ^[3]; ^[2]; ^[2]; ^[3]; ^[4]

Univ. of Alabama, Tuscaloosa, AL (United States); The University of Alabama
Univ. of Alabama, Tuscaloosa, AL (United States)
Stockholm Univ. (Sweden)
Univ. of Alabama, Tuscaloosa, AL (United States); Stockholm Univ. (Sweden)

Utilizing an ionic liquid strategy, we report crystal structures of salts of free anionic nucleobases and base pairs previously studied only computationally and in the gas phase. Reaction of tetrabutylammonium ([N₄₄₄₄]⁺) or tetrabutylphosphonium ([P₄₄₄₄]⁺) hydroxide with adenine (HAd) and thymine (HThy) led to hydrated salts of deprotonated adenine, [N₄₄₄₄][Ad]·2H₂O, and thymine, [P₄₄₄₄][Thy]·2H₂O, as well as the double salt cocrystal, [P₄₄₄₄]₂[Ad][Thy]·3H₂O·2HThy. The cocrystal includes the anionic [Ad-(HThy)] base pair which is a stable formation in the solid state that has previously not even been suggested. It exhibits Watson–Crick connectivity as found in DNA but which is unusual for the free neutral base pairs. The stability of the observed anionic bases and their supramolecular formations and hydrates has also been examined by electronic structure calculations, contributing to more insight into how base pairs can bind when a proton is removed and highlighting mechanisms of stabilization or chemical transformation in the DNA chains.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Alabama, Tuscaloosa, AL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Swedish Research Council (VR); Royal Swedish Academy of Science

Grant/Contract Number:: SC0019220

OSTI ID:: 1657346

Alternate ID(s):: OSTI ID: 2565332

Journal Information:: Proceedings of the National Academy of Sciences of the United States of America, Journal Name: Proceedings of the National Academy of Sciences of the United States of America Journal Issue: 31 Vol. 117; ISSN 0027-8424

Publisher:: National Academy of SciencesCopyright Statement

Country of Publication:: United States

Language:: English

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59 BASIC BIOLOGICAL SCIENCES
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CCDC 1976655: Experimental Crystal Structure Determination Kumar, Mishra, Manish; P., Kelley, Steven; Volodymyr, Smetana, https://doi.org/10.5517/ccdc.csd.cc24bw2g The current record is supplemented by this dataset	dataset	January 2020
CCDC 1976656: Experimental Crystal Structure Determination Kumar, Mishra, Manish; P., Kelley, Steven; Volodymyr, Smetana, https://doi.org/10.5517/ccdc.csd.cc24bw3h The current record is supplemented by this dataset	dataset	January 2020
CCDC 1976657: Experimental Crystal Structure Determination Kumar, Mishra, Manish; P., Kelley, Steven; Volodymyr, Smetana, https://doi.org/10.5517/ccdc.csd.cc24bw4j The current record is supplemented by this dataset	dataset	January 2020

Crystallographic evidence of Watson–Crick connectivity in the base pair of anionic adenine with thymine

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