Synthesis and properties of oligonucleotides containing C8-deoxyguanosine arylamine adducts of borderline carcinogens.
C8-Arylamine-dG adducts of borderline carcinogens and the bladder and breast carcinogen 4-aminobiphenyl were prepared using cross-coupling chemistry. These adducts were converted into the corresponding C8-arylamine-5'-O-DMTr-2'-deoxyguanosine phosphoramidites and then used as building blocks for automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were characterized by UV melting temperature analysis, enzymatic digestion, and circular dichroism.
Böge
Nicolas
N
Institute of Organic Chemistry, Department of Chemistry, Faculty of Mathematics, Informatics and Natural Sciences, University of Hamburg, Martin-Luther-King-Platz 6, D-20149 Hamburg, Germany.
Gräsl
Sonja
S
Meier
Chris
C
D000588:Amines / Q000737:chemistry*; D002273:Carcinogens / Q000737:chemistry*; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D002273:Carcinogens; D009841:Oligonucleotides; D003849:Deoxyguanosine