Heil, Korbinian; Pearson, David; Carell, Thomas
Chemical investigation of light induced DNA bipyrimidine damage and repair.
In: Chemical Society Reviews, Vol. 40: pp. 4271-4278
In all organisms, genetic information is stored in DNA and RNA. Both of these macromolecules
are damaged by many exogenous and endogenous events, with UV irradiation being one of the
major sources of damage. The major photolesions formed are the cyclobutane pyrimidine dimers
(CPD), pyrimidine–pyrimidone-(6-4)-photoproducts, Dewar valence isomers and, for dehydrated
spore DNA, 5-(a-thyminyl)-5,6-dihydrothymine (SP). In order to be able to investigate how
nature’s repair and tolerance mechanisms protect the integrity of genetic information,
oligonucleotides containing sequence and site-specific UV lesions are essential. This tutorial review
provides an overview of synthetic procedures by which these oligonucleotides can be generated,
either through phosphoramidite chemistry or direct irradiation of DNA. Moreover, a brief
summary on their usage in analysing repair and tolerance processes as well as their biological
effects is provided.