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Enantioselective Fluorescence Recognition of Free α-Amino Acids by Ion-Type Ammonium Salt-Based Sensors

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Abstract

Optically pure amino acids have extensive applications in pharmaceuticals, pesticides, food, materials, and other fields. Enantiomers recognition of chiral amino acids using optical methods with synthetic chiral sensors has attracted extensive attention. Most reported sensors typically identify guests by covalent or hydrogen bonding or hydrophobic interaction with amino acids and their derivatives. In this paper, a series of ion-type quaternary ammonium salt-based enantioselective fluorescent sensors were synthesized for chiral recognition of free α-amino acids via electrostatic interaction. The fluorescence intensity ratios ID/IL (ID, IL, fluorescence intensity of sensor when treated with D- or L-amino acid) were up to 2.1 and enantioselective fluorescence enhancement ratios ef (ef=[IL−I0]/[ID−I0] or [ID−I0]/[IL−I0]. (I0, fluorescence intensity of the sensor)) were up to 5.0. Among them, sensor 3 showed best enantioselective recognition performance toward tryptophan (Trp), and L-Trp significantly quenched the fluorescence of sensor 3, but D-Trp greatly enhanced the fluorescence of sensor 3, its ID/IL was 2.11 and ef was 1.8. The mechanistic investigation by NMR spectrum revealed that a tight three-point interaction, including electrostatic interaction, hydrogen bond, and π-π stacking, between sensor 3 and D-Trp was formed.

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Data Availability

The data generated and analyzed will be made available upon reasonable request from the corresponding author.

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Acknowledgements

The authors acknowledge financial support by the National Natural Science Foundation of China (NSFC), the Natural Science Foundation of Gansu Province, the Science and Technology Plan Foundation of Lanzhou, the Young Teacher Research Foundation of Northwest Normal University.

Funding

This work was supported by the National Natural Science Foundation of China (NSFC, Grant Nos. 22367021 and 22061025), the Natural Science Foundation of Gansu Province (Grant Nos. 21JR7RA124), the Science and Technology Plan Foundation of Lanzhou (Grant Nos. 2023-3-113), the Young Teacher Research Foundation of Northwest Normal University (Grant No. NWNU-LKQN2019-15).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, China

    Lei Bai, Chunyang Li & Dandan Wei

  2. School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou, 730070, China

    Changming Xu

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Contributions

L.B. designed the experiments and wrote the manuscript, C.L. and D.W. completed all experimental work, C.X. provided supervision and completed review.

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Correspondence to Lei Bai.

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Bai, L., Li, C., Wei, D. et al. Enantioselective Fluorescence Recognition of Free α-Amino Acids by Ion-Type Ammonium Salt-Based Sensors. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03568-7

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