8. C5′-Radical Generation and Reactivity in DNA

8.1. C5′-Radical Formation

The C5′-hydrogen atoms are even more accessible to diffusible species than the C4′-position (Fig. 1A) and this site has been suggested to be the preferred position for hydrogen atom abstraction by HO•.34 A variety of minor groove-binding DNA oxidizing agents abstract the C5′-hydrogen atom, including manganese porphyrins and the enediyne antitumor antibiotics, resulting in strand scission.120,176178 C5′-Deuterium-labelled DNA substrates were commonly used for detecting hydrogen atom abstraction from this position by the antitumour antibiotics.123 Frequently, the deuterium was used to reduce strand scission and/or shift reaction to another nucleotide position (eg C4′) resulting ...

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