Design of a coumarin-based triketone as a fluorescent protecting group for primary amines.
A series of 3-acetyl-4-hydroxycoumarin and its derivatives were prepared and evaluated for their potential to function as a fluorescent primary amine protection group. When primary amines or amino acids react with the protecting group 3-acetyl-4-methoxy-7- N, N-dimethylaminocoumarin, the resulting compounds emit blue fluorescence with a quantum yield of 0.25-0.50 in methylene chloride. These protected compounds display satisfactory acid/base stability, and the protecting group can be removed with 5% hydrazine hydrate in DMF within 5 min at ambient temperature.
Kuo
Pei-Yu
PY
Department of Chemistry, Tunghai University, 181, Taichung-Kang Road Sec. 3, Taichung, Taiwan 407, ROC.
Yang
Ding-Yah
DY