Abstract
This outlook describes two strategies to simultaneously determine the enantiomeric composition and concentration of a chiral substrate by a single fluorescent measurement. One strategy utilizes a pseudoenantiomeric sensor pair that is composed of a 1,1′-bi-2-naphthol-based amino alcohol and a partially hydrogenated 1,1′-bi-2-naphthol-based amino alcohol. These two molecules have the opposite chiral configuration with fluorescent enhancement at two different emitting wavelengths when treated with the enantiomers of mandelic acid. Using the sum and difference of the fluorescent intensity at the two wavelengths allows simultaneous determination of both concentration and enantiomeric composition of the chiral acid. The other strategy employs a 1,1′-bi-2-naphthol-based trifluoromethyl ketone that exhibits fluorescent enhancement at two emission wavelengths upon interaction with a chiral diamine. One emission responds mostly to the concentration of the chiral diamine and the ratio of the two emissions depends on the chiral configuration of the enantiomer but independent of the concentration, allowing both the concentration and enantiomeric composition of the chiral diamine to be simultaneously determined. These strategies would significantly simplify the practical application of the enantioselective fluorescent sensors in high-throughput chiral assay.
Highlights
The study of enantiomerically pure chiral compounds has found increasing importance in many areas, such as pharmaceutical industry [1, 2], agrochemical area [3], and food analysis [4, 5]
With the traditional analytical techniques, such as gas chromatography (GC) or high-performance liquid chromatography (HPLC), it usually takes about 20 min to determine the enantiomeric composition of a sample, which would be very inefficient for the analysis of the great number of products generated from the combinatorial catalyst screening processes
The difference of the fluorescence intensities at λ1 and λ2 could be utilized to measure the enantiomeric composition of mandelic acid (MA) and the sum could measure the total concentration
Summary
The study of enantiomerically pure chiral compounds has found increasing importance in many areas, such as pharmaceutical industry [1, 2], agrochemical area [3], and food analysis [4, 5]. The highly enantioselective fluorescent responses of these compounds make them useful in determining the enantiomeric composition of various chiral substrates. If both the concentration and enantiomeric composition of a chiral substrate could be determined by using one fluorescent measurement, it would significantly simplify the practical application of the enantioselective fluorescent recognition.
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