Control of Forward/Reverse Orientation Preference of Cyclic Pyrrole–Imidazole Polyamides
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- Yuki Hirose
- Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
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- Sefan Asamitsu
- Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
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- Toshikazu Bando
- Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
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- Hiroshi Sugiyama
- Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
書誌事項
- 公開日
- 2019-08-09
- 資源種別
- journal article
- 権利情報
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- https://doi.org/10.15223/policy-029
- https://doi.org/10.15223/policy-037
- https://doi.org/10.15223/policy-045
- DOI
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- 10.1021/jacs.9b05516
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
Pyrrole-imidazole polyamides (PIPs) bind to predetermined double-stranded DNA sequences and selectively target a large variety of DNA sequences. Although the forward-binding (5'-3'/N-C) orientation, in which the N-terminus of PIPs faces the 5'-terminus of DNAs, is considered to be the main binding manner of PIPs, a reverse-binding (5'-3'/C-N) orientation, in which the C-terminus of PIPs faces the 3'-terminus of DNAs, sometimes causes unintended binding. Here, we synthesized optical or structural isomers of previously reported cyclic PIPs (cPIPs), which differ in the position of the amino groups in the γ-turn units, and we investigated their binding affinities both in the forward- and reverse-binding orientation. We show that cPIPs with (R)-α-amino-γ-turn units prefer the forward orientation as do hairpin PIPs. More importantly, we document for the first time the remarkable reverse-binding preference of cPIPs with (S)-α-amino-γ-turns. These results indicate that the orientation preference of cPIPs can be controlled by the position of the amino groups on the γ-turn units, which may markedly increase the number of DNA sequences that can be targeted by PIPs.
収録刊行物
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- Journal of the American Chemical Society
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Journal of the American Chemical Society 141 (33), 13165-13170, 2019-08-09
American Chemical Society (ACS)
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詳細情報 詳細情報について
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- CRID
- 1361694367953595392
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- ISSN
- 15205126
- 00027863
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- 資料種別
- journal article
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- データソース種別
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- Crossref
- KAKEN
- OpenAIRE
