Enantioseparation via Chiral Supramolecular Gels Comprising Ambidextrous Gelators Based on ß-Peptide-type Primary Amines.

ABSTRACT

While ß-peptides have been paid attention due to their diverse secondary structures, their application to the design of low-molecular-weight gelators (LMWGs) is less explored. In this work, chiral cyclic ß-amino acid-based ß-peptides were developed as ambidextrous LMWGs, wherein multiple hydrogen bonds between the amide moieties led to high gelation ability. Their molecular assembly was elucidated using spectroscopies, microscopy, and X-ray analysis. Further, the supramolecular gel was used as a platform for the enantioselective extraction of (S)-naproxen from its racemate under optimized conditions. These findings have expanded the utility of ß-peptides and shown the potential of supramolecular gels as a distinct dynamic medium for enantiomer separation.