Stereoselective syntheses of fluorescent non-natural aromatic amino acids based on asymmetric Michael additions.
Four fluorescent non-natural aromatic amino acids have been synthesized based on a key stereoselective Michael addition reaction. S-1-phenylethylamine was employed as both the source of amine and the stereoselectivity controller. The overall yields were moderate (30-50%). Fluorescent properties of some of the fluorophores were also investigated. It was found that compounds with a dimethylamino group bonded to the aromatic ring display intramolecular charge transfer fluorescence.
Chen
Heru
H
Department of Chemistry, School of Sciences, Shantou University, Shantou, Guangdong 515063, PR China. hrchen@stu.edu.cn
Zhong
Xianbin
X
Wei
Jin
J
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005453:Fluorescence; D013237:Stereoisomerism
D000596:Amino Acids