Hydrogen-atom abstraction from the adenine-uracil base pair.

Hydrogen-atom abstraction from the adenine-uracil base pair. Research Abstract Details 

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Hydrogen-atom abstraction from the adenine-uracil base pair. Abstract Text:

Sunghwan Kim,Tyler Meehan,Henry F Schaefer,

The hydrogen-abstracted radicals from the adenine-uracil (AU) base pair have been studied at the B3LYP/DZP++ level of theory. The A(N9)-U and A-U(N1) radicals, which correspond to hydrogen-atom abstraction at the adenine N9 and uracil N1 atoms, respectively, were predicted to be the two lowest-lying among the nine (AU-H) radicals studied in this study. The removal of the amino hydrogen of the adenine moiety that forms a hydrogen bond with the uracil O4 atom in the AU pair resulted in radical A(N6a)-U, which has the smallest base-pair dissociation energy, 5.9 kcal mol(-1). This radical is more likely to dissociate into the two isolated bases than to recover the hydrogen bond with the O4 atom through N6-H bond rotation along the C6-N6 bond. In general, the radicals generated by C-H bond breaking were higher in energy than those arising from N-H bond cleavage, because the unpaired electrons in the carbon-centered radicals were mainly localized on the carbon atom from which the hydrogen atom was removed. However, the highest-lying radical was found to arise from removal of the N3 hydrogen of uracil. The most remarkable structural feature of this radical is a very short C-H...O distance of 2.094 A, consistent with a substantial hydrogen bond. Although this radical lost the N1...H-N3 hydrogen bond between the two bases, its dissociation energy was predicted to be 12.9 kcal mol(-1), similar to that of the intact AU base pair. This is due to the transfer of electron density from the adenine N1 atom to the uracil N3 atom.

Hydrogen-atom abstraction from the adenine-uracil base pair. Publishing Authors By Initials

S Kim,T Meehan,HF Schaefer,

For similar heterocyclic compounds: heterocyclic compounds, 1-ring: pyrimidines: pyrimidinones: uracil research abstracts see: heterocyclic compounds: heterocyclic compounds, 1-ring: pyrimidines: pyrimidinones: uracil research

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Hydrogen-atom abstraction from the adenine-uracil base pair. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: The journal of physical chemistry. A

VOLUME: 111

Page Numbers: 6806-12

Journal Abbreviation:

ISSN: 1089-5639

DAY: 15

MONTH: 03

YEAR: 2007

Hydrogen-atom abstraction from the adenine-uracil base pair. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 9890903

Hydrogen-atom abstraction from the adenine-uracil base pair. Keywords Mesh Terms:

KEYWORDS: Uracil

MESH TERMS: chemistry

Chemical & Substance for Abstract: Hydrogen-atom abstraction from the adenine-uracil base pair. Information

Substance Name: DNA

Registry Number: 9007-49-2

Grant and Affiliation Information for Hydrogen-atom abstraction from the adenine-uracil base pair.

AFFILIATION: Center for Computational Chemistry, University of Georgia, Athens, Georgia 30602, USA.

Country: United States

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MEDLINETA: J Phys Chem A

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