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Enantioseparation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide and Macrocyclic Glycopeptide Chiral Stationary Phases

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Abstract

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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  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles Street, Riga, 1006, Latvia

    Helena Kažoka, Baiba Turovska, Toms Upmanis & Grigory Veinberg

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  1. Helena Kažoka
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  2. Baiba Turovska
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  3. Toms Upmanis
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  4. Grigory Veinberg
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Correspondence to Helena Kažoka.

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Kažoka, H., Turovska, B., Upmanis, T. et al. Enantioseparation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide and Macrocyclic Glycopeptide Chiral Stationary Phases. Chromatographia 85, 489–495 (2022). https://doi.org/10.1007/s10337-022-04145-z

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  • DOI: https://doi.org/10.1007/s10337-022-04145-z

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