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


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.

SUBMITTER: Price NE 

PROVIDER: S-EPMC3954461 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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

Price Nathan E NE   Johnson Kevin M KM   Wang Jin J   Fekry Mostafa I MI   Wang Yinsheng Y   Gates Kent S KS  

Journal of the American Chemical Society 20140220 9


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  ...[more]

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