Effects of the 2-substituted adenosine-1,3-diazaphenoxazine 5′-triphosphate derivatives on the single nucleotide primer extension reaction by DNA polymerase

Yosuke Taniguchi, Ikuko Sagara, Yusuke Nagata, Yoshiya Kikukawa, Shigeki Sasaki

研究成果: ジャーナルへの寄稿記事

抄録

The adenosine triphosphate derivatives of 2-oxo-1,3-diazaphenoxazine (dAdapTP) showed a significant discrimination ability for the template strand including that between 8-oxo-2′-deoxyguanosine (8-oxodG) and 2′-deoxyguanosine (dG) by the single nucleotide primer extension reaction using the Klenow Fragment. In this study, we synthesized new dAdapTP derivatives, i.e., 2-amino-dAdapTP, 2-chloro-dAdapTP and 2-iodo-dAdapTP, to investigate the effect on the selectivity and efficiency of incorporation for the primer extension reaction using a variety of DNA polymerases. In contrast to the previously tested dAdapTP, the selectivity and efficiency of the 2-halo-dAdapTP incorporation were dramatically decreased using the Klenow Fragment. Moreover, the efficiency of the 2-amino-dAdapTP incorporation into the T-containing template was almost the same with that of dAdapTP. In the case of the Bsu DNA polymerase, the efficiency of all the dAdapTP derivatives decreased compared to that using the Klenow Fragment. However, the incorporation selectivity of dAdapTP had improved against the oxodG-containing template for all the template sequences including the T-containing template. Moreover, 2-amino-dAdapTP showed a better efficiency than dAdapTP using the Bsu DNA polymerase. The 2-amino group of the adenosine unit may interact with syn-oxodG at the active site of the Bsu DNA polymerase during the single primer extension reaction.

元の言語英語
ページ(範囲)1123-1130
ページ数8
ジャーナルChemical and Pharmaceutical Bulletin
67
発行部数10
DOI
出版物ステータス出版済み - 1 1 2019

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DNA-Directed DNA Polymerase
DNA Polymerase I
Adenosine
Nucleotides
Derivatives
Deoxyguanosine
Catalytic Domain
Adenosine Triphosphate
1,3-diazaphenoxazine
triphosphoric acid

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

これを引用

Effects of the 2-substituted adenosine-1,3-diazaphenoxazine 5′-triphosphate derivatives on the single nucleotide primer extension reaction by DNA polymerase. / Taniguchi, Yosuke; Sagara, Ikuko; Nagata, Yusuke; Kikukawa, Yoshiya; Sasaki, Shigeki.

:: Chemical and Pharmaceutical Bulletin, 巻 67, 番号 10, 01.01.2019, p. 1123-1130.

研究成果: ジャーナルへの寄稿記事

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AB - The adenosine triphosphate derivatives of 2-oxo-1,3-diazaphenoxazine (dAdapTP) showed a significant discrimination ability for the template strand including that between 8-oxo-2′-deoxyguanosine (8-oxodG) and 2′-deoxyguanosine (dG) by the single nucleotide primer extension reaction using the Klenow Fragment. In this study, we synthesized new dAdapTP derivatives, i.e., 2-amino-dAdapTP, 2-chloro-dAdapTP and 2-iodo-dAdapTP, to investigate the effect on the selectivity and efficiency of incorporation for the primer extension reaction using a variety of DNA polymerases. In contrast to the previously tested dAdapTP, the selectivity and efficiency of the 2-halo-dAdapTP incorporation were dramatically decreased using the Klenow Fragment. Moreover, the efficiency of the 2-amino-dAdapTP incorporation into the T-containing template was almost the same with that of dAdapTP. In the case of the Bsu DNA polymerase, the efficiency of all the dAdapTP derivatives decreased compared to that using the Klenow Fragment. However, the incorporation selectivity of dAdapTP had improved against the oxodG-containing template for all the template sequences including the T-containing template. Moreover, 2-amino-dAdapTP showed a better efficiency than dAdapTP using the Bsu DNA polymerase. The 2-amino group of the adenosine unit may interact with syn-oxodG at the active site of the Bsu DNA polymerase during the single primer extension reaction.

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