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Nucleic Acids Research, 1991, Vol. 19, No. 8 1753-1758
© 1991

CHEMISTRY

Structure and in vitro replication of DNA templates containing 7,8-dihydro-8-oxoadenine

Wilhelm Guschlbauer1, Anne-Marie Duplaa, André Guy, Robert Téoule* and G.Victor Fazakerley1

Laboratoires de Chimie, Radiobiochimie, Département de Recherche Fondarnentale Centre d'Etudes Nucléaires de Grenoble BP 85X, 38041 Grenoble Cedex 1Service de Biochimie et de Génétique Moléculaire, Departement de Biologie Cellulaire et Moléculaire, Centre d'Etudes Nucléaires de Saclay 91191 Gif-sur-Yvette Cedex, France

* To whom correspondence should be addressed

Received February 11, 1991. Revised March 22, 1991. Accepted March 22, 1991.

Adenine residues in DNA are oxidized under the action of ionizing radiation at the C-B position to give 7,8-dihydro-8-oxoadenine. The formation of this lesion can be considered a cause of mutations and carcinogenesis. Oligodeoxyrlbonucleotides 39 and 47 bases long containing a single 7,8-dihydro-8- oxoadenine (8-hydroxyadenine) residue were synthesized by using nucieoside phosphoramidites. They were used as templates to study the copies obtained in vitro by the Kienow fragment and the thermostable Taq DNA poiymerase. 7,8-Dihydro-8- oxoadenine does not block the replication and thymine is incorporated opposite the damage. The modifications of the DNA duplex conformation provoked by 7,8-dihydro-8-oxoadenine are minor. 1H NMR spectroscopy shows that the duplex is in a B form, the sugar in a normal position in the helix and the modified base in the anti position. NMR confirms that 7,8-dihydro-8-oxoadenine exists predominantly in the keto form.


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