Fluorescent/Colorimetric Dual-Mode Discriminating Gln and Val Enantiomers Based on Carbon Dots.

Discrimination and quantification of amino acid (AA) enantiomers are particularly important for diagnosing and treating diseases. Recently, dual-mode probes have gained a lot of research interest because they can catch more detecting information compared with the single-mode probes. Thus, it is of great significance to develop a dual-mode sensor realizing AA enantiomer discrimination conveniently and efficiently. In this work, carbon dot L-TCDs were prepared by N-methyl-1,2-benzenediamine dihydrochloride (OTD) and l-tryptophan. With the assistance of H2O2, L-TCDs show an excellent discrimination performance for enantiomers of glutamine (Gln) and valine (Val) in both fluorescent and colorimetric modes. The fluorescence enantioselectivity of Gln (FD/FL) and Val (FL/FD) is 5.29 and 4.13, respectively, and the colorimetric enantioselectivity of Gln (ID/IL) and Val (IL/ID) is 13.26 and 3.42, individually. The chiral recognition mechanism of L-TCDs was systematically studied. L-TCDs can be etched by H2O2, and the participation of AA enantiomers results in different amounts of the released OTD, which provides fluorescent and colorimetric signals for identifying and quantifying the enantiomers of Gln and Val. This work provides a more convenient and flexible dual-mode sensing strategy for discriminating AA enantiomers, which is expected to be of great value in facile and high-throughput chiral recognition.

Modifying carbon dots with L-phenylalanine for rapid discrimination of tryptophan enantiomers.

New chiral carbon dots (CDs), L-PCDs, for discriminating tryptophan (Trp) enantiomers were prepared in this work. Firstly, original CDs were synthesized through a hydrothermal method using pyridine-2,6-dicarboxylic acid and o-phenylenediamine as raw materials. Then, the surface of original CDs was modified with L-phenylalanine to create chiral fluorescent carbon L-PCDs. In the presence of D-Trp, the fluorescence intensity of L-PCDs decreased significantly while it remained unchanged in the presence of L-Trp. The chiral sensing system used in this study has a rapid response time of 3 minutes and can identify enantiomers with an enantioselectivity (ID/IL) of up to 3.3. For D-Trp, a good linear relationship can be obtained in the range of 0.3-4.2 mM with a limit of detection of 0.06 mM. This sensor allows for both quantitative detection of D-Trp and determination of enantiomeric percentage in the racemate. The chiral recognition mechanism is attributed to the different interaction between D-/L-Trp and L-PCDs.