Convenient and Efficient Syntheses of Oligodeoxyribonucleotides Containing O -(Carboxymethyl)Guanine and O -(4-Oxo-4-(3-Pyridyl)Butyl)Guanine.

O 6-(carboxymethyl)guanine (O 6-CMG) and O 6-(4-oxo-4-(3-pyridyl)butyl)guanine (O 6-pobG) are toxic lesions formed in DNA following exposure to alkylating agents. O 6-CMG results from exposure to nitrosated glycine or nitrosated bile acid conjugates and may be associated with diets rich in red meat. O 6-pobG lesions are derived from alkylating agents found in tobacco smoke. Efficient syntheses of oligodeoxyribonucleotides (ODNs) containing O 6-CMG and O 6-pobG are described that involve nucleophilic displacement by the appropriate alcohol on a common synthetic ODN containing the reactive base 2-amino-6-methylsulfonylpurine. ODNs containing O 6-pobG and O 6-CMG were found to be good substrates for the S. pombe alkyltransferase-like protein Atl1. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental file.] [ABSTRACT FROM PUBLISHER]