Work

Reactions of Unsymmetric Chiral Dialdehydes with Lysine: Regio‐ and Enantioselective Macrocyclization and Fluorescent Sensing

Year: 2024

Type: article

Abstract: Three BINOL‐based unsymmetric chiral dialdehydes, (S)‐4, (S)‐5, and (S)‐6, each containing a salicylaldehyde moiety and an ortho‐, meta‐ or para‐substituted benzaldehyde unit, are synthesized and used to react with the enantiomers of an unsymmetric chiral diamine, lysine. These reactions represent the first examples of regioselective as well as enantioselective reactions of an unsymmetric chiral dialdehyde with an unsymmetric chiral diamine to generate unsymmetric chiral macrocycles. The addition of Zn2+ can further enhance the selectivity for the macrocycle formation. Compounds (S)‐4 and (S)‐5 are found to exhibit chemoselective and enantioselective fluorescent recognition of lysine in the presence of Zn2+.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202401250

Authors: Yifan Mao, Yichen Li, Stephanie Davis, Lin Pu

Institution: University of Virginia

Language: English

Topic: Molecular Sensors and Ion Detection

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science Foundation, University of Virginia, Division of Chemistry

Awards: G1605393264, Enantioselective Fluorescent Analysis of Amino Acids, G7196948224, Enantioselective Fluorescent Recognition of Amino Alcohols and Catalyst Screening