Chromatographic resolution of enantiomers : Selective review

Gas chromatography of amino acids.

A new class of hydrophilic, relatively polar liquid, cyclodextrin (CD) derivatives have been used as highly selective chiral stationary phases (CSPs) for capillary gas chromatography (GC). Several possible requirements for liquidity in CD derivatives are discussed. O-(S)-2-Hydroxypropyl derivatives of alpha-, beta-, and gamma-cyclodextrins were synthesized, exclusively characterized, permethylated, and evaluated for enantioselectivity. Seventy pairs of enantiomers were resolved. They represent a wide variety of structural types and classes of compounds including chiral alkyl amines, amino alcohols, epoxides, pyrans, furans, sugars, diols, esters, ketones, bicyclic compounds, alcohols, and so on. Many of these compounds were not aromatic and cannot be resolved on any known liquid chromatographic CSP. Often, these enantiomers had far less functionality than required for LC separation. General properties of these CSPs as well as possible insights into the separation mechanism are discussed.

Polar-liquid, derivatized cyclodextrin stationary phases for the capillary gas chromatography separation of enantiomers

Chemical Derivatization in Gas Chromatography

Gas chromatographic—mass spectrometric analysis of optically active metabolites and drugs on a novel chiral stationary phase

Resolution of Racemic Amino Acids by Gas Chromatography on Optically Active Stationary Phases

Rapid gas chromatographic separation of amino acid enantiomers using N-perfluoroacyl esters

Molecular interactions in a unique solvent—solute system

N-trifluoroacetyl-L-norvalyl-L-norvaline cyclohexyl ester as a stationary phase and its interaction with asymmetric solutes.

N-Trifluoroacetyl (TFA) dipeptide-o-carboranyl propyl esters of L-valyl-L-valine and L-α-amino-n-butyryl-L-α-amino-n-butyric acid have been prepared and the properties of these two new stationary phases for the gas-liquid chromatographic sepaation of amino acid enantiomers have been examined. It was found that the amino acid derivatives have shorter retention times, while maintaining good separation factors, on these carborane phases as compared to other dipeptide stationary phases. Both high and low boiling derivatives have been resolved on a 165 m×0.5 mm capillary column. The new phases have greater thermal stability and can be utilized over a wide temperature range.

The separation of amino acid enatiomers on optically active dipeptide carborane stationary phases

W. Parr

Papers

Resolution of Racemic Amino Acids by Gas Chromatography on Optically Active Stationary Phases

Rapid gas chromatographic separation of amino acid enantiomers using N-perfluoroacyl esters

Molecular interactions in a unique solvent—solute system

N-trifluoroacetyl-L-norvalyl-L-norvaline cyclohexyl ester as a stationary phase and its interaction with asymmetric solutes.

The separation of amino acid enatiomers on optically active dipeptide carborane stationary phases