New composite stationary phase for chiral high-performance liquid chromatography
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New composite stationary phase for chiral high-performance liquid chromatography D. S. Prosuntsova1 · A. Yu. Plodukhin1 · I. A. Ananieva1 · E. K. Beloglazkina1 · P. N. Nesterenko1,2 Accepted: 16 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The new composite chiral stationary phase for high-performance liquid chromatography was prepared and characterized. Poly(styrene-divinylbenzene) microspherical particles with diameter of 3.3 micron were used as a matrix and coated with layer of 10 nm gold nanoparticles. Immobilized gold nanoparticles increased specific surface area of adsorbent and simplify covalent attachment of sulfur-containing compounds. In this work l-lysine conjugate with lipoic acid was synthesized, characterized and used for modification of gold nanoparticles. The prepared chiral selector was immobilized by the reaction of sulfur-containing groups from lipoic acid residue with gold surface of nanoparticles with formation of self-assembled monolayer. The prepared chiral stationary phase was characterized by nitrogen adsorption at low temperatures, diffuse reflection spectroscopy, scanning electron microscopy. The chromatographic retention of beta-blockers and profens was studied under conditions of reversed-phase HPLC. The possibility of enantiomers separation was demonstrated for flurbiprofen and ketoprofen racemates using 100 × 4.6 mm ID chromatographic column. Keywords Chiral stationary phases · Gold nanoparticles · Enantiomers · Poly(styrene-divinylbenzene) · HPLC
1 Introduction It is well known that enantiomers of many essential drugs have different pharmaceutical activity. At present, many drugs having chiral center/s are marketed as a single pharmaceutically active enantiomer, but preparation of pure optical isomers is not a trivial task. For this reason, the separation of enantiomers is an important part of organic synthesis and medicinal chemistry. The most common solution of this problem is high-performance liquid chromatography (HPLC), which is widely used for separation and quantitative analysis of various classes of organic compounds including optical isomers. In the latter case, the successful separation of enantiomers requires the use of chromatographic systems containing, so called, chiral selectors either in mobile or in stationary phase. Obviously, to minimize the use of expensive chiral selectors it is more practical to use * D. S. Prosuntsova [email protected] 1
Chemistry Department, Lomonosov Moscow State University, 119991 Moscow, Russia
Australian Centre for Research on Separation Science, Hobart, Tasmania 7005, Australia
2
them in immobilized form. The corresponding adsorbents are called chiral stationary phases (CSP) and the corresponding separation mode got the name of chiral HPLC. CSPs for chiral HPLC can be classified according to the type of chiral selector as natural (chiral selectors are proteins, alkaloids, oligosaccharides, antibiotics), semi-synthetic (modified oligosaccharides, polysaccharides, low molecul
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