Development of bis-unsaturated ester aldehydes as amino-glue probes: Sequential double azaelectrocyclization as a promising strategy for bioconjugation

Katsunori Tanaka; Yuka Nakamoto; Eric R.O. Siwu; Ambara R. Pradipta; Koji Morimoto; Takeshi Fujiwara; Suguru Yoshida; Takamitsu Hosoya; Yuki Tamura; Go Hirai; Mikiko Sodeoka; Koichi Fukase

doi:10.1039/c3ob41507d

Development of bis-unsaturated ester aldehydes as amino-glue probes: Sequential double azaelectrocyclization as a promising strategy for bioconjugation

Katsunori Tanaka, Yuka Nakamoto, Eric R.O. Siwu, Ambara R. Pradipta, Koji Morimoto, Takeshi Fujiwara, Suguru Yoshida, Takamitsu Hosoya, Yuki Tamura, Go Hirai, Mikiko Sodeoka, Koichi Fukase

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

23 被引用数 (Scopus)

抄録

The unsaturated ester aldehyde, (E)-3-alkoxycarbonyl-5-phenyl-2,4-dienal, was efficiently dimerized by applying the strain-promoted double-click reaction with sym-dibenzo-1,5-cyclooctadiene-3,7-diyne. The resulting dimerized probe was sequentially reacted first with one peptide molecule and then with a protein or the amino groups on the surface of a live cell through double azaelectrocyclization to achieve highly efficient bioconjugation.

本文言語	英語
ページ（範囲）	7326-7333
ページ数	8
ジャーナル	Organic and Biomolecular Chemistry
巻	11
号	42
DOI	https://doi.org/10.1039/c3ob41507d
出版ステータス	出版済み - 11月 14 2013
外部発表	はい

!!!All Science Journal Classification (ASJC) codes

生化学
物理化学および理論化学
有機化学

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10.1039/c3ob41507d

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「Development of bis-unsaturated ester aldehydes as amino-glue probes: Sequential double azaelectrocyclization as a promising strategy for bioconjugation」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

Tanaka, K., Nakamoto, Y., Siwu, E. R. O., Pradipta, A. R., Morimoto, K., Fujiwara, T., Yoshida, S., Hosoya, T., Tamura, Y., Hirai, G., Sodeoka, M., & Fukase, K. (2013). Development of bis-unsaturated ester aldehydes as amino-glue probes: Sequential double azaelectrocyclization as a promising strategy for bioconjugation. Organic and Biomolecular Chemistry, 11(42), 7326-7333. https://doi.org/10.1039/c3ob41507d

Tanaka, K, Nakamoto, Y, Siwu, ERO, Pradipta, AR, Morimoto, K, Fujiwara, T, Yoshida, S, Hosoya, T, Tamura, Y, Hirai, G, Sodeoka, M & Fukase, K 2013, 'Development of bis-unsaturated ester aldehydes as amino-glue probes: Sequential double azaelectrocyclization as a promising strategy for bioconjugation', Organic and Biomolecular Chemistry, vol. 11, no. 42, pp. 7326-7333. https://doi.org/10.1039/c3ob41507d

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abstract = "The unsaturated ester aldehyde, (E)-3-alkoxycarbonyl-5-phenyl-2,4-dienal, was efficiently dimerized by applying the strain-promoted double-click reaction with sym-dibenzo-1,5-cyclooctadiene-3,7-diyne. The resulting dimerized probe was sequentially reacted first with one peptide molecule and then with a protein or the amino groups on the surface of a live cell through double azaelectrocyclization to achieve highly efficient bioconjugation.",

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T2 - Sequential double azaelectrocyclization as a promising strategy for bioconjugation

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AU - Nakamoto, Yuka

AU - Siwu, Eric R.O.

AU - Pradipta, Ambara R.

AU - Morimoto, Koji

AU - Fujiwara, Takeshi

AU - Yoshida, Suguru

AU - Hosoya, Takamitsu

AU - Tamura, Yuki

AU - Hirai, Go

AU - Sodeoka, Mikiko

AU - Fukase, Koichi

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