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© 1989 Oxford University Press

research-article

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

K. Pongracz , S. Kaur 1, A.L. Burlingame 1 and W.J. Bodell  2

1Mass Spectrometry Facility, Department of Pharamaceutical Chemistry, University of California San Francisco, CA 94143, USA
Brain Tumor Research Center of the Department of Neurological Surgery HSW-783

2To whom correspondence should be addressed

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 O6hydroxy-2-phenylethyl)-2'-deoxyguanosine-3', 5'-bisphosphate and adduct number 5 as O6-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3',5'-bishosphate.


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