Azido-coronatine: A useful platform for "click chemistry"- mediated probe synthesis for bioorganic studies

Masahiro Okada, Syuusuke Egoshi, Minoru Ueda

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

We report on the development of azide-coronatine as a useful platform for azide alkyne cycloaddition ("click chemistry")-mediated synthesis of molecular probes. (p)-Azido-coronatine was synthesized in 10 steps with 11% yield using improved synthesis of coronafacic acid, in which the highly exo-selective Diels-Alder reaction (endo:exo > 1:25) is the key step. Azido coronatine was as effective as the original coronatine in a stomatal opening assay, and was easily modified to a fluorescein isothiocyanate (FITC)-labeled probe with high yield.

Original languageEnglish
Pages (from-to)2092-2095
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume74
Issue number10
DOIs
Publication statusPublished - 2010

Keywords

  • Click chemistry
  • Coronatine
  • Fluorescence
  • Molecular probe
  • Stomatal opening

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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