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Studies on the mechanism of DNA sequence selective alkylation by kapurimycin A3 analogs
A Okamoto1, K Nakatani, I Saito
1Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, Japan.
Abstract:
We synthesized kapurimycin A3 ABCD-ring analog and compared the sequence selectivity for DNA guanine alkylation with those of kapurimycin A3 and ABC-ring analog. In the binding to DNA, it was shown by DNA unwinding assay that ABCD-ring analog binds tightly to DNA by intercalation into DNA duplex. DNA alkylation by ABCD-ring analog was sequence selective with an order of G*G > G*A > G*T > G*C. ABCD-ring analog has a stronger binding ability, a higher reactivity to DNA and a higher GG sequence selectivity in DNA alkylation than those to ABC-ring analog. The aromatic ring system plays an important role in the effective GG selective alkylation.