C-1′ hydrogen abstraction of deoxyribose in DNA strand scission by dynemicin A

Dynemicin A, which is a hybrid antitumor antibiotic containing anthraquinone and enediyne cores, abstracts the C-1′ hydrogen of DNA deoxyribose and then the damaged DNA leads to strand breaks with the formation of 5′- and 3′-phosphate termini. The lesions of C-4′ hydrogen also occur at 3′ side of G·C base pairs (i. e., 5′-CT and 5′-GA), leading to 5′-phosphate and 3′-phosphoglycolate termini or 4′-hydroxylated abasic sites. The C-1′ hydrogen abstraction by dynemicin A is distinct from the preferential C-5′ hydrogen abstraction of calicheamicin and neocarzinostatin.