An Oxidized Abasic Lesion as an Intramolecular Source of DNA Adducts
Lirui Guan A and Marc M. Greenberg A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Johns Hopkins University, 3400 N Charles Street, Baltimore, MD 21218, USA.
B Corresponding author. Email: mgreenberg@jhu.edu
Australian Journal of Chemistry 64(4) 438-442 https://doi.org/10.1071/CH10420
Submitted: 19 November 2010 Accepted: 18 December 2010 Published: 18 April 2011
Abstract
5′-(2-Phosphoryl-1,4-dioxobutane) (DOB) is a lesion produced in DNA via a variety of damaging agents. The DOB lesion spontaneously generates cis- and trans-but-2-en-1,4-dial (1) via β-elimination. Cis- and trans-but-2-en-1,4-dial forms exocyclic adducts with nucleosides. We used chemically synthesized DNA containing tritiated DOB incorporated at defined sites to examine the reactivity of cis- and trans-but-2-en-1,4-dial. Although the local DNA sequence does not appear to influence the distribution of nucleoside adducts, we find that DOB generates relatively high yields of cis- and trans-but-2-en-1,4-dial nucleoside adducts that likely are promutagenic.
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