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Immobilized strychnine as a new chiral stationary phase for HPLC

D. Sýkora, J. Vozka, E. Tesařová, K. Kalíková, M. Havlík, P. Matějka, V. Král,

. 2017 ; 38 (15) : 1956-1963. [pub] 20170519

Jazyk angličtina Země Německo

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc17030832

A new ion-exchanger type chiral stationary phase for high-performance liquid chromatography was prepared. The synthetic protocol is based on derivatization of silica with (3-iodopropyl)trimethoxysilane in the first step followed by immobilization of strychnine via quaternization of nitrogen atom of the alkaloid strychnine. The synthesized chiral stationary phase was chromatographically characterized. The main effort was headed towards the evaluation of the enantioselectivity of the novel sorbent. For that purpose a set of suitable chiral probes, specifically, binaphthyl derivatives, was employed. The influence of methanol content, concentration of aqueous ammonium acetate buffer, and its pH on retention factors, separation selectivity, and resolution of the atropoisomers of the mentioned chiral solutes was studied in detail. It was demonstrated that the new chiral stationary phase was capable to separate atropoisomers of four out of seven testing compounds. Despite the strong influence of the above mentioned variables on retention, their impact on selectivity and resolution was rather moderate. Concerning retention mechanism, it seems that electrostatic interaction between the positively charged quaternary nitrogen of the chiral stationary phase and anionic solute participates significantly in the retention process.

Citace poskytuje Crossref.org

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$a A new ion-exchanger type chiral stationary phase for high-performance liquid chromatography was prepared. The synthetic protocol is based on derivatization of silica with (3-iodopropyl)trimethoxysilane in the first step followed by immobilization of strychnine via quaternization of nitrogen atom of the alkaloid strychnine. The synthesized chiral stationary phase was chromatographically characterized. The main effort was headed towards the evaluation of the enantioselectivity of the novel sorbent. For that purpose a set of suitable chiral probes, specifically, binaphthyl derivatives, was employed. The influence of methanol content, concentration of aqueous ammonium acetate buffer, and its pH on retention factors, separation selectivity, and resolution of the atropoisomers of the mentioned chiral solutes was studied in detail. It was demonstrated that the new chiral stationary phase was capable to separate atropoisomers of four out of seven testing compounds. Despite the strong influence of the above mentioned variables on retention, their impact on selectivity and resolution was rather moderate. Concerning retention mechanism, it seems that electrostatic interaction between the positively charged quaternary nitrogen of the chiral stationary phase and anionic solute participates significantly in the retention process.
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$a Vozka, Jiří $u Department of Analytical Chemistry, University of Chemistry and Technology Prague, Prague, Czech Republic. Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
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$a Tesařová, Eva $u Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
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$a Kalíková, Květa $u Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
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$a Havlík, Martin $u Department of Analytical Chemistry, University of Chemistry and Technology Prague, Prague, Czech Republic. First Faculty of Medicine, Charles University, Prague 2, Czech Republic.
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$a Matějka, Pavel $u Department of Physical Chemistry, University of Chemistry and Technology Prague, Prague, Czech Republic.
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$a Král, Vladimír $u Department of Analytical Chemistry, University of Chemistry and Technology Prague, Prague, Czech Republic. First Faculty of Medicine, Charles University, Prague 2, Czech Republic.
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