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Issue 42, 2013
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Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation

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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.

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

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Publication details

The article was received on 23 Jul 2013, accepted on 30 Aug 2013 and first published on 02 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41507D
Citation: Org. Biomol. Chem., 2013,11, 7326-7333
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    Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation

    K. Tanaka, Y. Nakamoto, E. R. O. Siwu, A. R. Pradipta, K. Morimoto, T. Fujiwara, S. Yoshida, T. Hosoya, Y. Tamura, G. Hirai, M. Sodeoka and K. Fukase, Org. Biomol. Chem., 2013, 11, 7326
    DOI: 10.1039/C3OB41507D

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