Identification of alkylation products of styrene oxide in single- and double-stranded DNA

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Abstract
Radioactive styrene oxide was reacted with double-and single-stranded DNA and the binding products were characterized by HPLC after neutral hydrolysis and enzyme digestion of DNA. More products were formed in single-stranded DNA as compared with double-stranded DNA. In single-stranded DNA at least 95% of the adducts were guanine N -7-, N2 and O6 -alkylation products; they were formed in proportions 54:33:12. In double-standed DNA the respective proportion was 74:23:3.7, indicating a selective suppression of alkylation at atoms N2 and, particularly, O6 that take part in hydrogen bonding in double-standed DNA. The α and β-isomers of 7-alkylguanine were formed in a similar proportion in single and double-stranded DNA, indicating no steric hindrance.