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Chiroptical-responsive nanoprobe for the optosensing of chiral amino acids

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Abstract

A supersensitive chiroptical-responsive system of enantioselectively recognizing L- and D-tryptophan (Trp) based on ( +)-diacetyl-L-tartaric anhydride-functionalized 1,3,5-triformylphloroglucinol (DTA-functionalized Tp) was constructed for the first time. With a high fluorescence quantum yield of 15.2% and fluorescence lifetime of 57.6 μs, DTA-functionalized Tp as both fluorescent and chiral recognition nanoprobe was used for the discrimination of L- and D-Trp with excitation/emission maxima at 330/490 nm within 3 min. The linear range of the fluorescence sensing was 0.002–0.15 μg mL−1, and the detection limit achieved 1.4 ng mL−1. Furthermore, a smartphone was employed as a detector and processor to couple with the chiroptical-responsive nanoprobe for establishing a novel and visual integration system for rapid and real-time detection of chiral amino acids with a detection limit of 13 ng mL−1. The spiked recoveries of L-Trp in two commercially available functional beverages ranged from 86.00 to 118.33% in fluorescence and smartphone-based sensing system. Based on the excellent chiroptical-responsive effects, high stability, and biocompatibility, the chiroptical-responsive nanoprobe was successfully applied to visual optosensing and fluorescence imaging in response to L- and D-Trp in HeLa cells. This discrimination methodology with high sensitivity and enantioselectively shows great potential for in-site visually monitoring chiral amino acids in real food samples and tracking physiological processes.

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Funding

This work was supported by the National Natural Science Foundation of China (No. 31822040, 32072335) and the National Key R&D Program of China (No. 2018YFC1602300).

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  1. Yuan Zhao and Xinyue Yuan contributed equally to this work.

Authors and Affiliations

  1. Beijing Technology and Business University, No. 11 Fucheng Road, Beijing, 100048, People’s Republic of China

    Yuan Zhao, Xinyue Yuan, Wei Jiang, Huilin Liu & Baoguo Sun

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  1. Yuan Zhao
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Correspondence to Huilin Liu.

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Zhao, Y., Yuan, X., Jiang, W. et al. Chiroptical-responsive nanoprobe for the optosensing of chiral amino acids. Microchim Acta 189, 184 (2022). https://doi.org/10.1007/s00604-022-05282-w

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