title: Oligonucleotides damaged with carcinogenic aromatic amines at the C8- and N6-position of 2'-deoxyadenosine.
abstract: The synthesis of C8- and N(6)-adducts of 2'- deoxyadenosine with carcinogenic aromatic amines is described. Furthermore, the adducts were converted into their corresponding phosphoramidites. These were applied to solid phase DNA synthesis to obtain the site-specifically modified oligonucleotides that were characterized and investigated regarding melting temperature, circular dichroism spectra and in some cases by enzymatic degradation assays.
authors.affiliation: Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther- King Platz 6, 20146 Hamburg, Germany.
authors.forename: Maike I
authors.initials: MI
authors.lastname: Jacobsen
authors.forename: Chris
authors.initials: C
authors.lastname: Meier
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002273:Carcinogens / Q000737:chemistry*; D018736:DNA Adducts / Q000138:chemical synthesis* / Q000737:chemistry; D004249:DNA Damage; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry
chemical_list: D002273:Carcinogens; D018736:DNA Adducts; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D000241:Adenosine