title: 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.
abstract: 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 (R1), as well as in the ester group (R2) 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 enantiomers 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 (R1) and/or the ester group (R2) 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 R1 and R2 alkyl groups. It was found that the temperature dependencies of selectivity factors, ln alpha on 1/T, were mostly non-linear. The thermodynamic data [delta(deltaS) and [delta(deltaH)] 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.
authors.affiliation: Department of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinskeho 9, SK-81237 Bratislava, Slovak Republic.
authors.forename: Ivan
authors.initials: I
authors.lastname: Spanik
authors.forename: Jan
authors.initials: J
authors.lastname: Krupcik
authors.forename: Ivan
authors.initials: I
authors.lastname: Skacáni
authors.forename: Pat
authors.initials: P
authors.lastname: Sandra
authors.forename: Daniel W
authors.initials: DW
authors.lastname: Armstrong
mesh_terms: D000596:Amino Acids / Q000302:isolation & purification*; D002849:Chromatography, Gas / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003505:Cyclodextrins