Nov, 2006
Synthesis and photochemical properties of a new water-soluble coumarin, designed as a chromophore for highly water-soluble and photolabile protecting group
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
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- Volume
- 79
- Number
- 11
- First page
- 1753
- Last page
- 1757
- Language
- English
- Publishing type
- Research paper (scientific journal)
- Publisher
- CHEMICAL SOC JAPAN
The absorption spectra and fluorescence spectra of a coumarin derivative (1), designed to be a water-soluble photo-labile protecting group for caged compounds, were successfully observed in aqueous buffer solutions at pH 2.0-12.5 for the first time. Coumarin 1 is highly soluble (> 5 mM) in aqueous buffer at pH 7.2 and is stable in the dark at room temperature for up to a week. The pK(a) value for the protonation of anilino nitrogen in coumarin 1 was determined to be 4.5. Coumarin I has a fluorescence lifetime of 2.0 ns and undergoes intersystem crossing to the triplet state. Therefore, compound 1 can be used for the light absorbing part of the new water-soluble caged compounds, such as caged amino acids or caged nucteotides, which can release free amino acids or nucleotides, respectively, by excitation in the visible region.
- Link information
- ID information
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- ISSN : 0009-2673
- eISSN : 1348-0634
- Web of Science ID : WOS:000243276100015