Comparative Enantioseparation of Monoterpenes by HPLC on Three Kinds of Chiral Stationary Phases with an On-Line Optical Rotatory Dispersion under Reverse Phase Mode.

Abstract

HPLC enantioseparation of chiral monoterpenes was studied using amylose (AD-H), cellulose (OD-H) and ␤-cyclodextrin (CD-Ph), phenyl carbamate derivatives as chiral stationary phases (CSPs). The contributions of various functional groups of the chiral monoterpenes in capacity factor (k), separation factor (␣) and resolution factor (Rs) were investigated. AD-H column clearly showed the chiral recognition in 7 chemicals from a total of 9 analytes and especially for linalool, while the CD-Ph column could achieve efficient enantioseparation on carvone. The enantioseparation mechanism between the analytes and the CSPs is discussed. Chiral HPLC system coupled with ORD detector could be applied to isolate and directly determine the configuration of (3S)-(+)-linalool, which is not commercially available. Moreover, 100% enantiomeric excess of the isolated (3S)-(+)-linalool was observed from the SPME-GCMS result. Additionally, enantioseparation of (3S)-(+)-linalool by preparative HPLC system offered a 500-fold higher sample loading capacity than that of GC.

Comparison of Chiral Chromatography Columns for Pharmaceutical Method Development

“…Normal-phase conditions are less attractive to the analytical chemist for this reason and deter laboratory efficiency. Reversed-phase chiral chromatography is described widely in the literature, and commercial columns for this application are readily available [42][43][44][45][46][47][48][49][50][51].…”

TAMOF-1 as a Versatile and Predictable Chiral Stationary Phase for the Resolution of Racemic Mixtures

“…Our studies led to the resolution of racemic mixtures of natural products such as terpenes, terpenoids, − dihydropyridine-based calcium channel blockers, − and P -stereogenic compounds. While a number of examples of chiral gas chromatography − have been published for some of the above-mentioned compounds, very few reports in HPLC are known. − The great advantage of our model is that it allows us to predict the elution order using as few explanatory variables as possible. However, it is difficult to predict the actual resolution in the separation of a mixture given the simplicity of the model as this depends on experimental kinetic factors and the subsequent optimization of the HPLC process.…”

Reliable HPLC separation, vibrational circular dichroism spectra, and absolute configurations of isoborneol enantiomers

“…Tamura's group reported the HPLC separation of nine chiral monoterpenes on amylose, cellulose, and β-cyclodextrin phenylcarbamate chiral stationary phases in the reversed-phase mode. 15 The amylose column showed a good chiral recognition performance for seven analytes, especially for linalool, and the configuration of linalool was directly determined with this chiral HPLC system coupled with an optical rotatory (OR) detector. However, the cellulose column showed a very poor ability in chiral recognition of these analytes.…”