Chiral separation of amino acids using a chiral crown ether by impregnation on a polymeric support and monoamine modified silica gel

A chiral monoaza-15-crown-5 ether derivative was prepared from l-Leucinol and used as a chiral stationary phase. The new chiral stationary phases CSP-1 and CSP-2 were employed in separating the enantiomers of the sodium and potassium salts of amino acids. The sodium and potassium salt of the d-enantiomers of all amino acids (PhyAlaNa, PhyAlaK and PhyGlyNa, PhyGlyK, and TrpNa, TrpK) show higher selectivity than the l-enantiomers for both CSP-1 and CSP-2.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

(S)-2-Isobutyl-N-benzyl-4,7,10,13-tetraoxa-1-azacyclopentadec-8-eneC25H35NO4[α]D20=-11.6 (c 1.4, CHCl3)Source of chirality: (S)-leucinolAbsolute configuration: S