Abstract
A systematic study of enantioresolution of a library of xanthonic derivatives, prepared “in-house”, was successfully carried out with four commercially available macrocyclic glycopeptide-based columns, namely ChirobioticTM T, ChirobioticTM R, ChirobioticTM V and ChirobioticTM TAG. Evaluation was conducted in multimodal elution conditions: normal-phase, polar organic, polar ionic and reversed-phase. The effects of the mobile phase composition, the percentage of organic modifier, the pH of the mobile phase, the nature and concentration of different mobile phase additives on the chromatographic parameters are discussed. ChirobioticTM T and ChirobioticTM V, under normal-phase and reversed-phase modes, respectively, presented the best chromatographic parameters. Considering the importance of understanding the chiral recognition mechanisms associated with the chromatographic enantioresolution, and the scarce data available for macrocyclic glycopeptide-based columns, computational studies by molecular docking were also carried out.
Highlights
In order to further explore the effectiveness of this type of columns to separate the enantiomers of this important class of compounds, we describe a systematic study of enantioresolution using a larger library of chiral xanthonic derivatives and different mobile phases in normal-phase mode (NPM), polar organic mode (POM), polar ionic mode (PIM), and reversed-phase mode (RPM)
Poor enantioresolution were obtained, which prompted us to pursue our investigation increasing the library of compounds and the variables of the mobile phase to better understand the behavior of these chiral columns towards the target analytes
A library of thirty-one chiral xanthonic analytes (Figure 2) was used for the systematic study of enantioresolution, including the previous seven enantiomeric pairs [21] and more twenty-four [22], applying the chiral columns based on these four macrocyclic glycopeptide selectors
Summary
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