title: Chemical investigation of light induced DNA bipyrimidine damage and repair.
abstract: 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-(α-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.
authors.affiliation: Center for Integrative Protein Science CiPSM at the Department of Chemistry and Biochemistry, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, D-81377 Munich, Germany.
authors.forename: Korbinian
authors.initials: K
authors.lastname: Heil
authors.forename: David
authors.initials: D
authors.lastname: Pearson
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: D004249:DNA Damage; D004260:DNA Repair; D008027:Light; D009841:Oligonucleotides / Q000138:chemical synthesis*; D011740:Pyrimidine Dimers / Q000737:chemistry*; D013941:Thymine / Q000031:analogs & derivatives* / Q000737:chemistry; D014466:Ultraviolet Rays
chemical_list: D009841:Oligonucleotides; D011740:Pyrimidine Dimers; C009484:5-thyminyl-5,6-dihydrothymine; D013941:Thymine