Recent advances in chiral liquid chromatography stationary phases for pharmaceutical analysis

Liu, Huifeng; Wu, Zhihai; Chen, Jia; Wang, Jianhua; Qiu, Hongdeng

doi:10.1016/j.chroma.2023.464367

Cited by 12 publications

(2 citation statements)

References 126 publications

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“…18,19 Cyclodextrins are cyclic oligosaccharides made up of glucopyranose units building different ring sizes, namely α-cyclodextrins (six glucopyranose units), β-cyclodextrins (seven glucopyranose units) and γ-cyclodextrins (eight glucopyranose units). They can be used either immobilized or coated onto the stationary phase in gas chromatography (GC) 20 or HPLC columns 21,22 or as mobile phase additive in HPLC. 23,24 Also, cyclodextrins are used as chiral additives in the background electrolyte in capillary electrophoresis (CE).…”

Section: Introductionmentioning

confidence: 99%

Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

Hubner,

Schützinger,

Molnárová

et al. 2024

Chirality

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Among different substance classes, New Psychoactive Substances (NPS) comprise chiral amphetamines for stimulant and empathic effects. There is little knowledge in terms of clinical studies about possibly different effects of the two enantiomers of novel amphetamine derivatives. For this reason, there is a big demand for enantioseparation method development of this new substance class.Regarding gas chromatography, cyclodextrins proved to be effective for enantioseparation of NPS. In our attempt, an Astec® Chiraldex™ G‐PN column containing 2,6‐di‐O‐pentyl‐3‐propionyl‐γ‐cyclodextrin and a Lipodex™ D column containing heptakis‐(2,6‐di‐O‐pentyl‐O‐acetyl)‐β‐cyclodextrin as chiral selector served as stationary phases in a Shimadzu GCMS‐QP2010 SE system.Because of the special coating, maximum temperature is limited to 200 °C isothermal or 220 °C in programmed mode. To ensure detection, trifluoroacetic anhydride (TFAA) was used to increase sample volatility.1 As a result, 35 amphetamines were tested as their TFAA‐derivatives.A screening method with a temperature gradient from 140 °C to 200 °C at a heating ramp of 1 °C per minute and final time of 5 min, showed baseline separation for seven and partial separations for 16 trifluoro acetylated amphetamines using the Chiraldex™ G‐PN column. Six baseline and nine partial separations were observed with the Lipodex™ D column, respectively.

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Section: Introductionmentioning

confidence: 99%

Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

Hubner,

Schützinger,

Molnárová

et al. 2024

Chirality

View full text Add to dashboard Cite

show abstract

“…The application of NMR spectroscopy for this purpose has been summarized in [3][4][5][6] and reviews on molecular modeling approaches for separation sciences can be found in [6][7][8][9][10][11]. Within the reviewed period of time, the progress in the development of chiral stationary phases (CSPs) for highperformance liquid chromatography (HPLC) [26][27][28] and gas chromatography [29] was provided and an overview of chiral mobile phase additives in chromatography was published [30].…”

Section: Introductionmentioning

confidence: 99%

Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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The stereospecific analysis of chiral molecules is an important issue in many scientific fields. In separation sciences, this is achieved via the formation of transient diastereomeric complexes between a chiral selector and the selectand enantiomers driven by molecular interactions including electrostatic, ion‐dipole, dipole‐dipole, van der Waals or π‐π interactions as well as hydrogen or halogen bonds depending on the nature of selector and selectand. Nuclear magnetic resonance spectroscopy and molecular modeling methods are currently the most frequently applied techniques to understand the selector‐selectand interactions at a molecular level and to draw conclusions on the chiral separation mechanism. The present short review summarizes some of the recent achievements for the understanding of the chiral recognition of the most important chiral selectors combining separation techniques with molecular modeling and/or spectroscopic techniques dating between 2020 and early 2024. The selectors include polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, donor‐acceptor type selectors, ion‐exchangers, crown ethers, and molecular micelles. The application of chiral ionic liquids and chiral deep eutectic solvents, as well as further selectors, are also briefly addressed. A compilation of all published literature on chiral selectors has not been attempted.

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Chiral separation of D,L‐phenylglycine by cellulose triacetate membranes

Zhao,

Cui,

Yuan

2024

J of Applied Polymer Sci

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Enantiopure pharmaceuticals are especially important in medicinal applications. Phenylglycine, as a critical pharmaceutical intermediate, is often utilized in single enantiomeric form for drug synthesis. Chiral membrane separation offers advantages such as simple operation, low energy consumption, and scalability, holding great potential for chiral drug separations. In this work, cellulose triacetate (CTA) membranes are prepared via phase inversion and used for permeation experiments driven by a concentration gradient to investigate selective permeation of D,L‐phenylglycine solutions. Scanning electron microscopy reveals surface and cross‐sectional morphologies of the fabricated membranes. After single‐factor optimization, the CTA membrane exhibits an enantiomeric excess of 68.94% for D,L‐phenylglycine separation. The membrane maintains its selective permeation capability after repeated use. This indicates the CTA membrane has favorable chiral selective permeation for D,L‐phenylglycine solutions with stable performance. The chiral carbon on the six‐membered ring of the CTA backbone, as well as the single‐handed helical structure of the backbone, are thought to be responsible for the chiral selectivity of the membrane. This is the first report of using CTA membranes for chiral amino acid separation, providing experimental references and theoretical basis for membrane separation of racemic mixtures. It could facilitate scalable applications of chiral membranes.

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Recent advances in chiral liquid chromatography stationary phases for pharmaceutical analysis

Cited by 12 publications

References 126 publications

Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

Update on chiral recognition mechanisms in separation science

Chiral separation of D,L‐phenylglycine by cellulose triacetate membranes

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