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 journalArticle

20 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 languageEnglish
Pages (from-to)7326-7333
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number42
DOIs
Publication statusPublished - Nov 14 2013
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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