Journal
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
Volume 74, Issue 10, Pages 2092-2095Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1271/bbb.100518
Keywords
coronatine; click chemistry; molecular probe; fluorescence; stomatal opening
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Funding
- MEXT [20310128]
- AsahiGlass Foundation
- TOREY Foundation
- Naito Foundation
- Grants-in-Aid for Scientific Research [20310128] Funding Source: KAKEN
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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 Die Is-Alder reaction (endo:exo > 1:25) is the key step. Azido coronatine was as effective as the original coronatine in a stomata! opening assay, and was easily modified to a fluorescein isothiocyanate (FITC)-labeled probe with high yield.
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