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Chromatographic Enantiomer Separation Using 9-Amino-9-(deoxy)-epiquinine-derived Chiral Selectors: Control of Chiral Recognition via Introduction of Additional Stereogenic Centers

, : Chromatographic Enantiomer Separation Using 9-Amino-9-(deoxy)-epiquinine-derived Chiral Selectors: Control of Chiral Recognition via Introduction of Additional Stereogenic Centers. Acta Chimica Slovenica 59(3): 454-463

Three new cinchona-type chiral selectors have been prepared by attaching N-pivaloyl-glycine, N-pivaloyl-(S)-valine and N-pivaloyl-(R)-valine segments to the C9-amino function of 9-amino-9-(deoxy)-epiquinine (eAQN), and immobilized to silica to provide the corresponding chiral stationary phases (CSPs). Evaluation of the chromatographic enantioseparation characteristics of these CSPs with a broad assortment of N-carbamoyl protected amino acids under polar organic mobile phase conditions revealed modest chiral recognition capabilities for N-Fmoc-, N-Cbz- and N-Boc-derivatives. It was found that the enantioselective analyte binding to these CSPs is strictly controlled by the absolute stereo-chemistry of the amino acid functionalities attached to the C9-amino group of the eAQN framework. Specifically, the CSP derived from (S)-valine-based selector exhibits preferential binding of N-carbamoyl-(S)-amino acids, while the CSPs featuring (R)-valine- and the glycine-derived selectors show opposite enantioselective binding preference. The observed impact of analyte structure on enantioselectivity and the specific preferences in enantioselective binding point to chiral recognition mechanisms capitalizing on intermolecular ion pairing, hydrogen bonding and subtle steric interactions, with the latter making the crucial contributions to stereodiscrimination. The finding that the chiral recognition characteristics of epiquinine can be readily controlled via incorporation of additional stereogenic centers remote from the cinchona scaffold might be useful information for the design of new enantioselective receptors and organocatalysts.


PMID: 24061297

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