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  • Title: Azido-coronatine: a useful platform for "click chemistry"-mediated probe synthesis for bioorganic studies.
    Author: Okada M, Egoshi S, Ueda M.
    Journal: Biosci Biotechnol Biochem; 2010; 74(10):2092-5. PubMed ID: 20944396.
    Abstract:
    We report on the development of azide-coronatine as a useful platform for azide alkyne cycloaddition ("click chemistry")-mediated synthesis of molecular probes. (+)-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.
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