Interstrand DNA-DNA cross-link formation between adenine residues and abasic sites in duplex DNA.

Citation:
Price, N. E., K. M. Johnson, J. Wang, M. I. Fekry, Y. Wang, and K. S. Gates, "Interstrand DNA-DNA cross-link formation between adenine residues and abasic sites in duplex DNA.", Journal of the American Chemical Society, vol. 136, issue 9, pp. 3483-90, 2014 Mar 5.

Abstract:

The loss of a coding nucleobase from the structure of DNA is a common event that generates an abasic (Ap) site (1). Ap sites exist as an equilibrating mixture of a cyclic hemiacetal and a ring-opened aldehyde. Aldehydes are electrophilic functional groups that can form covalent adducts with nucleophilic sites in DNA. Thus, Ap sites present a potentially reactive aldehyde as part of the internal structure of DNA. Here we report evidence that the aldehyde group of Ap sites in duplex DNA can form a covalent adduct with the N(6)-amino group of adenine residues on the opposing strand. The resulting interstrand DNA-DNA cross-link occurs at 5'-ApT/5'-AA sequences in remarkably high yields (15-70%) under physiologically relevant conditions. This naturally occurring DNA-templated reaction has the potential to generate cross-links in the genetic material of living cells.

Notes:

n/a