Enantioselective Recognition of L-Lysine by ICT Effect with a Novel Binaphthyl-Based Complex

Abstract

A novel triazole fluorescent sensor was efficiently synthesized using binaphthol as the starting substrate with 85% total end product yield. This chiral fluorescence sensor was proved to have high specific enantioselectivity for lysine. The fluorescence intensity of R-1 was found to increase linearly when the equivalent amount of L-lysine (0–100 eq.) was gradually increased in the system. The fluorescence intensity of L-lysine to R-1 was significantly enhanced, accompanied by the red-shift of emission wavelength (389 nm to 411 nm), which was attributed to the enhanced electron transfer within the molecular structure, resulting in an ICT effect, while the fluorescence response of D-lysine showed a decreasing trend. The enantioselective fluorescence enhancement ratio for the maximum fluorescence intensity was 31.27 [ef = |(IL − I0)/(ID − I0)|, 20 eq. Lys], thus it can be seen that this fluorescent probe can be used to identify and distinguish between different configurations of lysine.

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

“…[11] L-lysine has multiple functions, including enhancing immunity, promoting skeletal muscle growth, facilitating fat metabolism, and alleviating anxiety. [12][13][14][15]Additionally, it can also Disclaimer/Publisher's Note: The statements, opinions, and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions, or products referred to in the content.…”

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

“…[11] L-lysine has multiple functions, including enhancing immunity, promoting skeletal muscle growth, facilitating fat metabolism, and alleviating anxiety. [12][13][14][15]Additionally, it can also produce synergistic effects with other nutrients and promote their absorption, improving the utilization efficiency of various nutrients, and thereby better expressing the physiological functions of different nutrients. [16,17] A deficiency in D-lysine may lead to adverse health reactions, including uremia.…”