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Nucleic Acids Research 2005 33(5):1637-1643; doi:10.1093/nar/gki305
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Published online 18 March 2005

© The Author 2005. Published by Oxford University Press. All rights reserved
The online version of this article has been published under an open access model. Users are entitled to use, reproduce, disseminate, or display the open access version of this article for non-commercial purposes provided that: the original authorship is properly and fully attributed; the Journal and Oxford University Press are attributed as the original place of publication with the correct citation details given; if an article is subsequently reproduced or disseminated not in its entirety but only in part or as a derivative work this must be clearly indicated. For commercial re-use, please contact journals.permissions{at}oupjournals.org

Article

The effect of the 2-amino group of 7,8-dihydro-8-oxo-2'-deoxyguanosine on translesion synthesis and duplex stability

Natsuhisa Oka and Marc M. Greenberg*

Department of Chemistry, Johns Hopkins University 3400 N. Charles St, Baltimore, MD 21218, USA

*To whom correspondence should be addressed. Tel: +1 410 516 8095; Fax: +1 410 516 7044; Email: mgreenberg{at}jhu.edu

Received January 14, 2005. Revised February 25, 2005. Accepted February 25, 2005.

Replication of DNA containing 7,8-dihydro-8-oxo-2'-deoxyguanosine (OxodG) gives rise to G -> T transversions. The syn-isomer of the lesion directs misincorporation of 2'-deoxyadenosine (dA) opposite it. We investigated the role of the 2-amino substituent on duplex thermal stability and in replication using 7,8-dihydro-8-oxo-2'-deoxyinosine (OxodI). Oligonucleotides containing OxodI at defined sites were chemically synthesized via solid phase synthesis. Translesion incorporation opposite OxodI was compared with 7,8-dihydro-8-oxo-2'-deoxyguanosine (OxodG), 2'-deoxyinosine (dI) and 2'-deoxyguanosine (dG) in otherwise identical templates. The Klenow exo– fragment of Escherichia coli DNA polymerase I incorporated 2'-deoxyadenosine (dA) six times more frequently than 2'-deoxycytidine (dC) opposite OxodI. Preferential translesion incorporation of dA was unique to OxodI. UV-melting experiments revealed that DNA containing OxodI opposite dA is more stable than when the modified nucleotide is opposed by dC. These data suggest that while duplex DNA accommodates the 2-amino group in syn-OxodG, this substituent is thermally destabilizing and does not provide a kinetic inducement for replication by Klenow exo–.


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