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Chemoselective and enantioselective fluorescent recognition of lysine by a BINOL-pyridine-based chiral dialdehyde

Year: 2026

Type: article

Abstract: A BINOL-pyridine-based chiral unsymmetric dialdehyde was synthesized. This compound in combination with Zn 2+ has exhibited highly chemoselective as well as enantioselective fluorescent response toward lysine, an essential amino acid. It was found that this compound undergoes regioselective macrocyclization with l -lysine but generates a more complex mixture with d -lysine. This difference in reactivity should contribute to the observed chemo- and enantioselectivty in the fluorescence response. This molecular probe can be used at 20 times lower concentration than a previously reported analog for lysine recognition. It has also displayed significantly enhanced enantioselectivity over the previously reported analog with the enantioselective fluorescence intensity ratio (ef) increased from 16.9 to 60.0 [ef = (I L -I 0 )/(I D -I 0 ). I 0 : the fluorescence intensity of the probe in the absence of the amino acid].

Source: Tetrahedron Letters

DOI: 10.1016/j.tetlet.2026.155959

Authors: Yichen Li, Lin Pu

Institution: University of Virginia

Language: English

Topic: Molecular Sensors and Ion Detection

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,610

Funders: National Science Foundation, Directorate for Mathematical and Physical Sciences