Site-specific synthesis and analysis of oligonucleotides containing the C8-deoxyguanosine adducts of the dietary mutagen 2-amino-3-methylimidazo[4,5-f]quinoline

The synthesis of a 2'-deoxyguanosine modified at the C8-position with the food mutagen 2-amino-3-methylimidazo[4,5- f]quinoline (IQ) and subsequent site-specific synthesis of oligonucleotides containing this adduct using phosphoramidite chemistry are presented in this thesis. The adducted oligonucleotides were studied using circular dichroism (CD) and absorbance spectroscopy. The spectra obtained were highly dependent on the sequence of the adducted oligonucleotide. This indicated that the IQ-adduct may be in different conformations dependent upon sequence. An attempt was made to correlate the specific conformation of the adduct with the mutagenic response of IQ and related adducts.