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Nucleic Acids Research, 2003, Vol. 31, No. 3 1045-1051
© 2003 Oxford University Press

Stability of 2'-deoxyxanthosine in DNA

Viengsai Vongchampa, Min Dong, Lakshman Gingipalli and Peter Dedon*

Biological Engineering Division, 56-787, Massachusetts Institute of Technology, Cambridge, MA 02139, USA

*To whom correspondence should be addressed. Tel: +1 617 253 8017; Fax: +1 617 258 0225; Email: pcdedon{at}mit.edu
Present address:
Lakshman Gingipalli, ArQule Inc., 19 Presidential Way, Woburn, MA 01801-5140, USA

The deamination of nucleobases in DNA occurs by a variety of mechanisms and results in the formation of hypoxanthine from adenine, uracil from cytosine, and xanthine and oxanine from guanine. 2'-Deoxyxanthosine (dX) has been assumed to be an unstable lesion in cells, yet no study has been performed under biological conditions. We now report that dX is a relatively stable lesion at pH 7, 37°C and 110 mM ionic strength, with a half-life (t1/2) of 2.4 years in double-stranded DNA. The stability of dX as a 2'-deoxynucleoside (t1/2 = 3.7 min at pH 2; 1104 h at pH 6) was increased substantially upon incorporation into a single-stranded oligodeoxynucleotide, in which the half-life of dX at different pH values was found to range from 7.7 h at pH 2 to 17 700 h at pH 7. Incorporation of dX into a double-stranded oligodeoxynucleotide resulted in a statistically insignificant increase in the half-life to 20 900 h at pH 7. Data for the pH dependence of the stability of dX in single-stranded DNA were used to determine the rate constants for the acid-catalyzed (2.6 x 10–5 s–1) and pH-independent (1.4 x 10–8 s–1) depurination reactions for dX as well as the dissociation constant for the N7 position of dX (6.1 x 10–4 M). We conclude that dX is a relatively stable lesion that could play a role in deamination-induced mutagenesis.


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