title: Convenient and efficient syntheses of oligodeoxyribonucleotides containing O(6)-(carboxymethyl)guanine and O(6)-(4-oxo-4-(3-pyridyl)butyl)guanine.
abstract: 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.
authors.affiliation: Centre for Chemical Biology, Department of Chemistry, Krebs Institute, University of Sheffield, Sheffield S3 7HF, UK.
authors.forename: Christopher L
authors.initials: CL
authors.lastname: Millington
authors.forename: Amanda J
authors.initials: AJ
authors.lastname: Watson
authors.forename: Andrew S
authors.initials: AS
authors.lastname: Marriott
authors.forename: Geoffrey P
authors.initials: GP
authors.lastname: Margison
authors.forename: Andrew C
authors.initials: AC
authors.lastname: Povey
authors.forename: David M
authors.initials: DM
authors.lastname: Williams
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000378:metabolism; D001483:Base Sequence; D006147:Guanine / Q000031:analogs & derivatives* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: C473029:O(6)-(4-oxo-4-(3-pyridyl)butyl)guanine; D009838:Oligodeoxyribonucleotides; D006147:Guanine; C510506:ATL1 protein, S pombe; D019883:Alkyl and Aryl Transferases