Chiroptical-responsive nanoprobe for the optosensing of chiral amino acids.

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.