Development of a chiral stationary phase based on cinchonidine. Comparison with a quinine‐based chiral column

Abstract

A chiral anion-exchanger stationary phase based on cinchonidine (CD) was developed. Two columns were packed with and without endcapping (EC) treatment (CD-chiral stationary phase[CD-CSP(EC)] and [CD-CSP], respectively) and studied for their ability to separate N-2,4-dinitrophenyl α-amino acids (DNP-amino acids) enantiomers over a temperature range of 10-40 °C with a hydro-organic buffer mobile phase. The more hydrophobic, endcapped stationary phase showed significantly larger retentive capacity than the non-endcapped one. The apparent thermodynamic transfer parameters of the enantiomers from the mobile to both CSPs were estimated from van't Hoff plots within the cited temperature range. Similar studies with two natural quinine-based columns (QN-CSP and QN-CSP(EC)) were previously reported. In this work, a critical comparison in the chiral recognition ability to DNP-amino acids of these cinchonidine and QN-based chiral columns was drawn. It has been found that QN-based CSPs show greater chiral recognition capability towards these derivatives than CD-CSPs. The influence of the QN methoxy group on the equilibrium constants of the enantioselective interaction between these DNP-amino acids with these two cinchona CSPs could be assessed.