Fluorescence recognition of lysine and a novel chiral BINOL complex calculated by using the Hildebrand-Benesi equation

A novel fluorescent sensor was efficiently synthesized by nucleophilic substitution, addition, and click reactions using binaphthyl phenol as a substrate. After the synthesis, a series of analyses were performed on the fluorescent sensor based on the database obtained from extensive testing experiments and the synthetic formulae. From the analysis of the test data, it was found that the fluorescence sensor showed high enantioselectivity for lysine after the addition of 15 amino acids, with L-lys showing an enhanced fluorescence response to the probe, while D-Lys was almost unchanged. In the presence of 20.0 eq. of lysine, the enantioselective fluorescence enhancement ratio was as high as 77.50. Therefore, the novel probe synthesized can be used to identify and distinguish between different conformations of lysine.