O6-substituted-2'-deoxyguanosine-3'-phosphate adducts detected by 32P post-labeling of styrene oxide treated DNA

Abstract

32P post-labeling of DNA reacted with styrene oxide resulted in the detection of six adducts. In order to determine which of these corresponded to modification at the O6 position of guanine, O6-substituted styrene oxide-deoxyguanosine-3'-monophosphate derivatives were synthesized. The two synthetic isomers were purified by HPLC and the structures were confirmed by mass spectrometry and 1H NMR. 32P post-labeling and co-chromatography with the DNA-styrene-7,8-oxide reaction products resulted in the assignment of adduct number 4 as O6-(2-hydroxy-2-phenylethyl)-2'--deoxyguanosine-3',5'-bisphosphate and adduct number 5 as O6-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3',5'-bisphosphate.