DNAインターカレーターによるグアニンアルキル化の配列選択性

  • 中谷 和彦
    京都大学大学院工学研究科合成・生物化学専攻
  • 齋藤 烈
    京都大学大学院工学研究科合成・生物化学専攻

書誌事項

タイトル別名
  • Sequence Selectivity for the Guanine Alkylation by DNA-Alkylating Intercalators.
  • DNA インターカレーター ニ ヨル グアニン アルキルカ ノ ハイレツ センタクセイ

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抄録

In order to gain insight into molecular basis for the sequence selective guanine alkylation by natural products aflatoxin B1 oxide and kapurimycin A3 we have synthesized epoxides with napthopyranone and anthrapyranone rings. Alkylation of guanine in DNA by these models proceeds with sequence selectivity similar to those of natural products. Absolute configuration of the epoxide side chain is significantly effective for the efficiency of guanine alkylation. Guanine alkylation most effectively proceeded at Gs in GG sequence, but G in the GC sequence was the least reactive site for the alkylation. The order of calculated energy levels of highest occupied molecular orbital (HOMO) for dinucleotide base pairs were in a good agreement with the G alkylation susceptibility experimentally obtained by our synthetic models. With these data we concluded that interaction of HOMO of DNA and LUMO of drugs is responsible for the sequence selectivity of guanine alkylation.

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