Stereoselective syntheses of fluorescent non-natural aromatic amino acids based on asymmetric Michael additions

Molecules. 2007 May 26;12(5):1170-82. doi: 10.3390/12051170.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Chromatography, High Pressure Liquid
  • Fluorescence
  • Stereoisomerism

Substances

  • Amino Acids