The gas-phase guest exchange reactions of a number of non-natural α-amino acids complexed to permethylated β-cyclodextrin were examined with Fourier transform mass spectrometry. The enantioselectivity of the reactions were determined. Molecular modeling calculations were performed to support the experimental results. The amino acids included homoserine, cis-4-hydroxyproline, allo-threonine, and allo-isoleucine. Results from molecular modeling calculations suggest that enantioselectivity is governed by differences in the binding interaction between the amino acid host and the permethylated β-cyclodextrin guest.
- Amino acids
- Chiral recognition
- Host-guest complexes
ASJC Scopus subject areas
- Physical and Theoretical Chemistry