期刊
JOURNAL OF SEPARATION SCIENCE
卷 41, 期 6, 页码 1355-1364出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jssc.201701213
关键词
chiral anion exchange; chiral stationary phases; click-chemistry immobilization; enantiomer separation; N-protected amino acids
资金
- Czech Science Foundation [16-17689Y]
- University of Vienna's IK Functional Molecules
- Michigan Institute for Clinical and Health Research [UL1TR000433]
In the enantiomeric separation of highly polar compounds, a traditionally challenging task for high-performance liquid chromatography, ion-exchange chiral stationary phases have found the main field of application. In this contribution, we present a series of novel anion-exchange-type chiral stationary phases for enantiomer separation of protected amino phosphonates and N-protected amino acids. Two of the prepared selectors possessed a double and triple bond within a single molecule. Thus, they were immobilized onto silica support employing either a thiol-ene (radical) or an azide-yne (copper(I)-catalyzed) click reaction. We evaluated the selectivity and the effect of immobilization proceeding either by the double bond of the Cinchona alkaloid or a triple bond of the carbamoyl moiety on the chromatographic performance of the chiral stationary phases using analytes with protecting groups of different size, flexibility, and pi-acidity. The previously observed preference toward protecting groups possessing pi-acidic units, which is a typical feature of Cinchona-based chiral stationary phases, was preserved. In addition, increasing the bulkiness of the selectors' carbamoyl units leads to significantly reduced retention times, while very high selectivity toward the tested analytes is retained.
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