Synthesis and Evaluation of Crown Ether Chiral Stationary Phase

In this paper, R-(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 was synthesized from (R)-1,1'-bi(2-naphthol), which was coated on C-18 silica gel (the average particle size is 5 mu m, and aperture is 120 angstrom). The final product (CSP) was used as the chiral stationary phase of high performance liquid chromatography for the enantioseparation of alpha-amino acids. In the conditions of perchloric acid solution (pH =2) as mobile phase, flow rate of 0.1 mL.min(-1), 25 degrees C, the chiral recognition ability for 13 kinds of alpha-amino acids enantiomer on CSP was studied, and 11 kinds of alpha-amino acid enantiomers (phenylglycine, hydroxyphenylglycine, methionine, tyrosine, tryptophan, valine, leucine, isoleucine, phenylalanine, glutamate, aspartate) were separated. This column offers a better enantioselectivity for six kinds of alpha-amino acid than that of commercial CR(+) column. The experimental results showed that CSP possesses a good enantioselectivity for alpha-amino acid enantiomers.