Issue 45, 2007
From the journal:

Physical Chemistry Chemical Physics

Hydrogen abstraction from deoxyribose by a neighbouring uracil-5-yl radical

Patric Schyman,*a   Ru bo Zhang,bc   Leif A. Eriksson*c  and  Aatto Laaksonena  

* Corresponding authors

a Division of Physical Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
E-mail: patric@physc.su.se.
Fax: +46 (0)8 152187
Tel: +46 (0)8 162373

b School of Science and the Institute for Chemical Physics, Beijing Institute of Technology, Beijing, China

c Department of Natural Sciences and Örebro Life Science Center, Örebro University, Örebro, Sweden
E-mail: leif.eriksson@nat.oru.se.
Fax: +46 (0)19 303566
Tel: +46 (0)19 303652

Abstract

Hydrogen abstraction from the C1′ and C2′ positions of deoxyadenosine by a neighbouring uracil-5-yl radical in the 5′-AU˙-3′ DNA sequence is explored using DFT. This hydrogen abstraction is the first step in a sequence leading to single or double strand break in DNA. The uracil-5-yl radical can be the result of photolysis or low-energy electron (LEE) attachment. If the radical is produced by photolysis the neighbouring adenine will become a cation radical and if it is produced by LEE the adenine will remain neutral. The hydrogen abstraction reactions for both cases were investigated. It is concluded that it is possible for the uracil-5-yl to abstract hydrogen from C1′ and C2′. When adenine is neutral there is a preference for the C1′ site and when the adenine is a radical cation the C2′ site is the preferred. If adenine is positively charged, the rate-limiting step when abstracting hydrogen from C1′ is the formation of an intermediate crosslink between uracil and adenine. This crosslink might be avoided in dsDNA, making C1′ the preferred site for abstraction.

Graphical abstract: Hydrogen abstraction from deoxyribose by a neighbouring uracil-5-yl radical

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Article information

DOI
https://doi.org/10.1039/B711083A
Article type
Paper
Submitted
19 Jul 2007
Accepted
11 Sep 2007
First published
27 Sep 2007

Phys. Chem. Chem. Phys., 2007,9, 5975-5979

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Hydrogen abstraction from deoxyribose by a neighbouring uracil-5-yl radical

P. Schyman, R. B. Zhang, L. A. Eriksson and A. Laaksonen, Phys. Chem. Chem. Phys., 2007, 9, 5975 DOI: 10.1039/B711083A

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