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

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7326-7333
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	42
DOIs	https://doi.org/10.1039/c3ob41507d
Publication status	Published - Nov 14 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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

year = "2013",

month = nov,

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doi = "10.1039/c3ob41507d",

language = "English",

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journal = "Organic and Biomolecular Chemistry",

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T1 - Development of bis-unsaturated ester aldehydes as amino-glue probes

T2 - Sequential double azaelectrocyclization as a promising strategy for bioconjugation

AU - Tanaka, Katsunori

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

PY - 2013/11/14

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AB - 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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JO - Organic and Biomolecular Chemistry

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

Abstract

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