Papers

Peer-reviewed
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
  • Naoko Senda
  • ,
  • Atsuya Momotake
  • ,
  • Yoshinobu Nishimura
  • ,
  • Tatsuo Arai

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
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000243276100015&DestApp=WOS_CPL
ID information
  • ISSN : 0009-2673
  • eISSN : 1348-0634
  • Web of Science ID : WOS:000243276100015

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