Chiral recognition by enantioselective liquid chromatography: Mechanisms and modern chiral stationary phases

Recent applications in chiral high performance liquid chromatography: a review.

This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

https://onlinelibrary.wiley.com/doi/pdf/10.1002/bdd.279

Chiral separation by chromatographic and electromigration techniques. A Review

The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/pdf/10.1002/jssc.200600046

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic-based chiral stationary phases: A review

The chiral resolution by high performance liquid chromatography (HPLC) is controlled by a number of parameters. The optimization of HPLC parameters is an important issue in chiral resolution. This review discusses the optimization of HPLC conditions for the chiral resolution of racemic drugs on polysaccharides and macrocyclic glycopeptide antibiotic chiral stationary phases (CSPs). The most important parameters discussed are composition of mobile phase, pH of mobile phase, flow rate, temperature and effect of other parameters.

Optimization strategies for HPLC enantioseparation of racemic drugs using polysaccharides and macrocyclic glycopeptide antibiotic chiral stationary phases

Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase

Study of the Origin and Mechanism of Band Pressure Drop in Centrifugal Countercurrent Broadening and Chromatography

The present invention relates to a novel stationary phase support for liquid chromatographic chiral separations. The specific combination of the special underlying support material and certain classes of known chiral selectors according to the invention produces far superior chiral (enantiomeric) separations than those obtained on any conventionally known supports. These chiral (enantiomeric) separations are enhanced in terms of significantly higher efficiencies (theoretical plate numbers), higher resolutions (Rs), shorter retention times and either equivalent or slightly higher selectivities than those obtained on conventional supports.

Daniel W. Armstrong

Papers

Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase

Study of the Origin and Mechanism of Band Pressure Drop in Centrifugal Countercurrent Broadening and Chromatography

New ultrahigh efficiency, superficially porous particle (spp) chiral phases for liquid chromatography

Superficially porous particle (SPP) chiral phases for liquid chromatography