Simultaneous determination of the concentration and enantiomeric excess of amino acids with a coumarin-derived achiral probe

Abstract

The chirality of amino acids plays an important role in biological and medical sciences. The development of achiral small-molecule probes that can simultaneously determine the absolute configuration, enantiomeric excess, and total concentration of amino acids is significant. We reported the currently available achiral coumarin aldehyde probe that could form Schiff bases with free amino acids at room temperature to induce CD signals and change UV-vis signals. The red-shifted UV-vis signals were independent of the substrate's chirality and could be used to determine the total concentration. Conversely, the enantioselective CD signals could be used to determine the absolute configuration and enantiomeric excess. The usefulness and practicability of this sensing method were demonstrated by analyzing 6 non-racemic phenylalanine samples with different enantiomeric compositions and concentrations.