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Kacprzak K, Maier N, Lindner W. Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. J Sep Sci. 2010;33(17):2590-8doi: 10.1002/jssc.201000393.
Kacprzak, K., Maier, N., & Lindner, W. (2010). Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. Journal of separation science, 33(17), 2590-8. https://doi.org/10.1002/jssc.201000393
Kacprzak, Karol, et al. "Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase." Journal of separation science vol. 33,17 (2010): 2590-8. doi: https://doi.org/10.1002/jssc.201000393
Kacprzak K, Maier N, Lindner W. Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. J Sep Sci. 2010 Sep;33(17):2590-8. doi: 10.1002/jssc.201000393. PMID: 20715146.
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J Sep Sci. 2010 Sep;33(17):2590-8. doi: 10.1002/jssc.201000393.

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase.

Journal of separation science

Karol Kacprzak, Norbert Maier, Wolfgang Lindner

Affiliations

  1. Department of Chemistry, Adam Mickiewicz University, Poznan, Poland. [email protected]

PMID: 20715146 DOI: 10.1002/jssc.201000393

Abstract

Replacement of the flexible thioether linker for the novel, rigid 1,2,3-triazole spacer group in the course of immobilization of quinine tert-butyl carbamate onto a silica surface led to a chiral stationary phase (CSP) with enhanced enantioselectivity for the resolution of mandelic acid and derivatives thereof. These new CSPs allowed efficient resolution of a wide set of mandelic acids with α-values between 1.08 and 1.68. The high loadability of these chiral ion exchange type CSPs allows preparative separation in the milligram range on an analytical column of 100×4 mm id in a single run as it was demonstrated for 4-trifluoromethylmandelic, 2-naphthylglycolic and 3,4-methylenedioxymandelic acids. The chiral recognition process has been studied using a library of 25 diverse racemic probes. A tentative model suggests that the rigid 1,2,3-triazole group takes part in the formation of an enantioselective-binding pocket of the entire and immobilized selector moiety of the CSP. The primary interaction site is given by the ionizable quinuclidine group of the Cinchona alkaloid supported by possible π-π stabilization effects within the selector-selectand complex.

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