On the capillary gas chromatographic separation of enantiomers of N-trifluoroacetyl-O-alkyl esters of selected amino acids on 2,3-di-O-pentyl-6-O-acyl cyclodextrins

摘要

In this work, the separation of enantiomers of N-TFA-O-alkyl amino acids on the 2,3-di-O-pentyl-6-O-acyl alpha-, beta- and gamma-cyclodextrin stationary phases has been studied. The influence of structure differences in the alkyl substituents bonded to the stereogenic carbon atom (R-1), as well as in the ester group (R-2) of the selected amino acid derivatives, and the selectivity of modified alpha-, beta- and gamma-cyclodextrin phases in gas chromatographic separation of derivatized amino acid enantiorners was studied in detail. A model set of N-TFA-alkyl esters of four amino acids was separated on five columns. The separation of enantiomers was evaluated in terms of the interactions of the alkyl substituents bonded to the stereogenic carbon (R-1) and/or the ester group (R-2) of the N-TFA-O-alkyl amino acid derivatives as well as the nature of the 3-O-acyl group in the 2,6-di-O-pentyl-3-O-acyl alpha-, beta- and gamma-cyclodextrins. It was shown that the variation in the enantiomeric separation with temperature and the retention order of enantiomers on a given cyclodextrin capillary column depends both on the nature of the bonded R-1 and R-2 alkyl groups. It was found that the temperature dependencies of selectivity factors, In alpha on 1/T, were mostly non-linear. The thermodynamic data {Delta(Delta S) and {Delta(Delta H)}} which characterize the chiral recognition were used to gain more insight into the mechanistic aspects of enantio separation of the N-TFA-O-alkyl amino acid derivatives on 2,6-di-O-pentyl-3-O-acyl-alpha, beta- and gamma-cyclodextrins. (c) 2004 Elsevier B.V. All rights reserved.