Chiral column chromatography

Chiral column chromatography is a variant of column chromatography in which the stationary phase contains a single enantiomer of a chiral compound rather than being achiral. The two enantiomers of the same analyte compound differ in affinity to the single-enantiomer stationary phase and therefore they exit the column at different times.

The chiral stationary phase can be prepared by attaching a suitable chiral compound to the surface of an achiral support such as silica gel, which creates a Chiral Stationary Phase (CSP). Many common chiral stationary phases are based on oligosaccharides such as cellulose or cyclodextrin (in particular with β-cyclodextrin, a seven sugar ring molecule). As with all chromatographic methods, various stationary phases are particularly suited to specific types of analytes.

Chiral Stationary Phases are much more expensive than comparable achiral stationary phases such as C₁₈.

The principle can be also applied to the fabrication of monolithic HPLC columns^[1] or gas chromatography columns.^[2]

References

↑ Yingjie Li; Chunhui Song; Lingyi Zhang; Weibing Zhang; Honggang Fu (January 2010). "Fabrication and evaluation of chiral monolithic column modified by β-cyclodextrin derivatives". Talanta. 80 (3): 1378–1384. doi:10.1016/j.talanta.2009.09.039. PMID 20006102.
↑ Yi-Ming Liu; Patricia Gordon; Shelby Green; Jonathan V. Sweedler (September 2000). "Determination of salsolinol enantiomers by gas chromatography-mass spectrometry with cyclodextrin chiral columns". Analytica Chimica Acta. 420 (1): 81–88. doi:10.1016/S0003-2670(00)00986-7.

Concepts in asymmetric synthesis

Chirality types	Chirality Stereocenter Planar chirality Chiral ligand Axial chirality Supramolecular chirality Inherent chirality

Chiral molecules	Stereoisomer Enantiomer Diastereomer meso compound racemic mixture Enantiomeric excess (ee) Diastereomeric excess (de)

Analysis	Optical rotation Chiral derivatizing agents NMR spectroscopy of stereoisomers Ultraviolet-visible spectroscopy of stereoisomers

Chiral resolution	Recrystallization Kinetic resolution Chiral column chromatography Diastereomeric recrystallization

Reactions	Asymmetric induction Chiral pool synthesis Chiral auxiliaries Asymmetric catalysis Organocatalysis Biocatalysis

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