Chromatographic enantioseparation of amino acids using a new chiral stationary phase based on a macrocyclic glycopeptide antibiotic

Abstract

The separation of the enantiomers of several a-amino acids was studied on a new chiral stationary phase (CSP) which is based on the macrocyclic glycopeptide antibiotic eremomycin attached to silica particles. Retention and separation factors were determined under analytical conditions at ambient temperature for different mobile phase compositions. In order to evaluate the potential with respect to preparative separations the adsorption isotherms of D- and L-methionine were determined for one mobile phase composition applying the elution by characteristic point method. The isotherms were validated by comparing experimentally determined elution profiles with predictions based on the equilibrium dispersive model. Finally, the performance of the eremomycin CSP was compared with a commercially available CSP based on the macrocyclic antibiotic teicoplanin. After determining the isotherms of D- and L-methionine also for the teicoplanin phase, the equilibrium dispersive model was used for both CSP to identify optimal operating conditions. For the separation and conditions considered the new eremomycin CSP revealed a better performance compared to the teicoplanin CSP.

Processes To Separate Enantiomers

“…In order to carry out a comparative study, in [298] two CSP based on macrocyclic glycopeptides were applied for the separation of the enantiomers of methionine, namely teicoplanin (i.e.…”

“…Experimental (symbols) and calculated (dotted) elution profiles of DL-methionine for the Chirasel E column, injection concentrations for both enantiomers: 6.1 gL -1 , the first peak corresponds to Lmethionine [298]. …”

Enantioseparation of racemic paroxol on an amylose‐based chiral stationary phase by supercritical fluid chromatography

“…In order to determine the isotherm parameters more accurately, the upper and lower 15% of rear part of the elution profiles were neglected. Typically, these parts differ more pronounced from the predicted results based on equilibrium model 25. The experimentally determined and predicted derivatives of the isotherms, d q /d c , are shown in Fig.…”

“…The column could be efficient enough once the number of theoretical plates obtained at analytical condition is more than 5000 23, 24. Thus, the axial dispersion coefficient can be treated as 0, and the ECP method can be used as an attractive method to estimate single‐component adsorption isotherms 17, 18, 24, 25. Besides the method is simple and fast, the consumption of substances during the experiments is relatively low, typically, only one overloaded elution profile is sufficient to obtain all information of the isotherms.…”

Experimental evaluation of the effect of a modified port‐location mode on the performance of a three‐zone simulated moving‐bed process for the separation of valine and isoleucine

“…A computer‐assisted simulation based on a detailed column model is one of the important tasks in the stage of developing a multicolumn separation process like SMB . The results from the detailed model simulation can allow us to predict solute migration behaviors in each column of SMB with high accuracy.…”