Issue 42, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Jul 2013
Accepted
30 Aug 2013
First published
02 Sep 2013

Org. Biomol. Chem., 2013,11, 7326-7333

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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