A new synthetic route to nucleotide adducts derived from N-acetylated and unacetylated 4-aminobiphenyl.
The carcinogen N-acetoxy-N-2-acetylaminofluorene reacts with dG and dG-containing nucleotides to give good yields of the C-8 adducts, but the analogous 4-aminobiphenyl derivative does not. Replacement of the N-acetoxy group by 2,6-dichlorobenzoyloxy circumvents this difficulty. This reaction is shown to be generally applicable, and biphenylamido adducts with dG, d(CpG), d(GpC) and d(ApG) have been prepared. A new, useful deacetylation procedure employing the heterogeneous system sodium carbonate/methanol which leads to the corresponding biphenylamino derivative without appreciable imidazole ring opening is also reported.
Underwood
G R
GR
Department of Chemistry, New York University, NY 10003.
Price
M F
MF
Shapiro
R
R
D000107:Acetylation; D000611:Aminobiphenyl Compounds / Q000138:chemical synthesis*; D004247:DNA / Q000378:metabolism; D003849:Deoxyguanosine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000611:Aminobiphenyl Compounds; D007202:Indicators and Reagents; D009711:Nucleotides; D004247:DNA; D003849:Deoxyguanosine