Enantioseparation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide and Macrocyclic Glycopeptide Chiral Stationary Phases
2022
Kažoka, Helena | Turovska, Baiba | Upmanis, Toms | Veinberg, Grigory
To extend our previous studies concerning the enantioseparation of 4C-substituted pyrrolidin-2-one derivatives on polysaccharide-based chiral stationary phases with ethanol/n-hexane mobile phases, two commercially available immobilized chiral stationary phases [amylose derivatized with (S)-α-methylbenzylcarbamate, and cellulose derivatized with 3,5-dichlorophenylcarbamate] were studied. Also, efforts to use macrocyclic glycopeptide (vancomycin, ristocetin A, teicoplanin, and teicoplanin aglycone) chiral stationary phases under normal-phase mode for enantioseparations of 4C-substituted pyrrolidin-2-one derivatives were made. It was established that both polysaccharide chiral stationary phases show high chiral recognition ability: 12 enantiomeric pairs on chiral selector cellulose tris (3,5-dichlorophenylcarbamate) and 11 enantiomeric pairs on chiral selector amylose tris [(S)-α-methylbenzylcarbamate] out of 15 enantiomeric pairs studied, separated with Rₛ ≥ 2. The results showed that the nature of the analyzed compounds plays an important role in chiral discrimination, especially in relation to CSPs based on macrocyclic glycopeptides: 4-aryl-pyrrolidin-2-ones could be resolved with Rₛ ≥ 2 on teicoplanin or teicoplanin aglycone chiral selectors, teicoplanin aglycone phase was able also to separate enantiomers of 4-aryl-substituted acetate derivatives, whereas 4-aryl-substituted acetamide derivatives only could be resolved on vancomycin phase.
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