Regio- and Enantioselective Macrocyclization from Dynamic Imine Formation: Chemo- and Enantioselective Fluorescent Recognition of Lysine

The dynamic covalent chemistry of imines is utilized to conduct a regioselective as well as enantioselective synthesis of an unsymmetric (C-1) chiral macrocycle from the reaction of an unsymmetric (C-1) chiral dialdehyde, (S)-4, that contains a salicylaldehyde unit and a benzaldehyde unit, with lysine, an unsymmetric (C-1) chiral diamine. The enantioselectivity is further enhanced in the presence of Zn2+. Compound (S)-4 in combination with Zn2+ is found to be a highly chemoselective as well as enantioselective fluorescent probe for lysine. It can be used to detect specific enantiomers of this amino acid.

Automated summary

The dynamic covalent chemistry of imines is used to synthesize an unsymmetric (C-1) chiral macrocycle from the reaction of an unsymmetric (C-1) chiral dialdehyde with lysine. The enantioselectivity is enhanced in the presence of Zn2+. The resulting compound is a highly selective fluorescent probe for lysine.