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Molecular Novelties in Chiral Enantioseparation and Discrimination
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Molecular Novelties in Chiral Enantioseparation and Discrimination

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: 20 March 2025 | Viewed by 3738

Special Issue Editor

Dr. Magdalena Małgorzata Urbańska

E-Mail Website
Guest Editor
Institute of Chemistry, Military University of Technology, ul. Sylwestra Kaliskiego 2, 00-908 Warsaw, Poland
Interests: liquid crystals; smectic chiral phases; antiferroelectric mixtures; orthoconic materials; organic synthesis; physical chemistry; chiral chromatography; HPLC; racemates

Special Issue Information

Dear Colleagues,

The possibility of direct separation of chiral isomers is extremely important in chemistry, both from an analytical and preparative point of view, especially in the case of pharmacological preparations. Chiral liquid chromatography is one of the most effective techniques for separating enantiomers and checking their optical purity. The rapid development of chiral chromatography dates back to the introduction of chiral stationary phases, additives to the mobile phase, and their commercialization. The emergence of a theory explaining the mechanism of chiral differentiation also contributed to the development of this technique. In recent years, chromatographic enantioseparations have developed significantly, and this separation procedure has become one of the most useful methods in many fields dealing with drugs, natural products, agrochemicals, etc. Due to the growing demand for enantiomerically pure compounds, effective strategies for the analytical and preparative separation of enantiomers are required.

This Special Issue aims to present and discuss the latest research results on the chromatographic separation of various groups of materials used in pharmacology, medicine, agrochemistry, organic chemistry, etc. Original research works in which UPLC and SFC techniques were used for separation are also welcome.

Dr. Magdalena Małgorzata Urbańska
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

  • chiral chromatography
  • enantiomers
  • racemates
  • enantioseparation
  • chiral stationary phases (CSPs)
  • high-performance liquid chromatography (HPLC)
  • ultra-performance liquid chromatography (UPLC)
  • supercritical fluid chromatography (SFC)

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Published Papers (4 papers)

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Research

13 pages, 2448 KiB  
Communication
1,3-Dithiolane as a Privileged Scaffold in Bioactive Derivatives: Chiral Resolution and Assignment of Absolute Configuration
by Roberta Listro, Giacomo Rossino, Valeria Cavalloro, Daniela Rossi, Massimo Boiocchi, Marina Simona Robescu, Teodora Bavaro, Silvia Franchini, Claudia Sorbi, Marco De Amici, Pasquale Linciano and Simona Collina
Int. J. Mol. Sci. 2024, 25(23), 12880; https://doi.org/10.3390/ijms252312880 - 29 Nov 2024
Viewed by 296
Abstract
The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characterization of the stereoisomers. We report the [...] Read more.
The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characterization of the stereoisomers. We report the first chiral resolution and absolute configuration (AC) assignment for (1,4-dithiaspiro[4.5]decan-2-yl)methanol (R/S)-1, a key synthon for dithiolane-based biologically active compounds. Using (semi)preparative enantioselective HPLC, we isolated enantiomeric 1. The AC was assigned by using (+)-1 for the enantioselective synthesis of (+)-BS148, a sigma receptor modulator. An X-ray diffraction analysis established the (R)-configuration of (+)-BS148 and, by extension, of (+)-1. This method provides a reliable approach for preparing enantiopure 1,3-dithiolane scaffolds and establishes reference standards for AC determination of related compounds. Full article
(This article belongs to the Special Issue Molecular Novelties in Chiral Enantioseparation and Discrimination)
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20 pages, 2360 KiB  
Article
Enantioselective Binding of Proton Pump Inhibitors to Alpha1-Acid Glycoprotein and Human Serum Albumin—A Chromatographic, Spectroscopic, and In Silico Study
by Gergely Dombi, Levente Tyukodi, Máté Dobó, Gergely Molnár, Zsuzsanna Rozmer, Zoltán-István Szabó, Béla Fiser and Gergő Tóth
Int. J. Mol. Sci. 2024, 25(19), 10575; https://doi.org/10.3390/ijms251910575 - 1 Oct 2024
Viewed by 917
Abstract
The enantioselective binding of three proton pump inhibitors (PPIs)—omeprazole, rabeprazole, and lansoprazole—to two key plasma proteins, α1-acid glycoprotein (AGP) and human serum albumin (HSA), was characterized. The interactions between PPI enantiomers and proteins were investigated using a multifaceted analytical approach, including high-performance liquid [...] Read more.
The enantioselective binding of three proton pump inhibitors (PPIs)—omeprazole, rabeprazole, and lansoprazole—to two key plasma proteins, α1-acid glycoprotein (AGP) and human serum albumin (HSA), was characterized. The interactions between PPI enantiomers and proteins were investigated using a multifaceted analytical approach, including high-performance liquid chromatography (HPLC), fluorescence and UV spectroscopy, as well as in silico molecular docking. HPLC analysis demonstrated that all three PPIs exhibited enantioseparation on an AGP-based chiral stationary phase, suggesting stereoselective binding to AGP, while only lansoprazole showed enantioselective binding on the HSA-based column. Quantitatively, the S-enantiomers of omeprazole and rabeprazole showed higher binding affinity to AGP, while the R-enantiomer of lansoprazole displayed greater affinity for AGP, with a reversal in the elution order observed between the two protein-based columns. Protein binding percentages, calculated via HPLC, were greater than 88% for each enantiomer across both transport proteins, with all enantiomers displaying higher affinity for AGP compared to HSA. Thermodynamic analysis indicated that on the HSA, the more common, enthalpy-controlled enantioseparation was found, while in contrast, on the AGP, entropy-controlled enantioseparation was observed. The study also identified limitations in using fluorescence titration due to the high native fluorescence of the compounds, whereas UV titration was effective for both proteins. The determined logK values were in the range of 4.47–4.83 for AGP and 4.02–4.66 for HSA. Molecular docking supported the experimental findings by revealing the atomic interactions driving the binding process, with the predicted enantiomer elution orders aligning with experimental data. The comprehensive use of these analytical methods provides detailed insights into the enantioselective binding properties of PPIs, contributing to the understanding of their pharmacokinetic differences and aiding in the development of more effective therapeutic strategies. Full article
(This article belongs to the Special Issue Molecular Novelties in Chiral Enantioseparation and Discrimination)
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15 pages, 5472 KiB  
Article
Elucidating Chiral Resolution of Aromatic Amino Acids Using Glycopeptide Selectors: A Combined Molecular Docking and Chromatographic Study
by Dehbiya Gherdaoui, Madiha Melha Yahoum, Selma Toumi, Sabrina Lekmine, Sonia Lefnaoui, Ouided Benslama, Rachida Bouallouche, Hichem Tahraoui, Mohammad Shamsul Ola, Ahmad Ali, Jie Zhang and Abdeltif Amrane
Int. J. Mol. Sci. 2024, 25(16), 9120; https://doi.org/10.3390/ijms25169120 - 22 Aug 2024
Viewed by 914
Abstract
An asymmetric synthesis is a favorable approach for obtaining enantiomerically pure substances, but racemic resolution remains an efficient strategy. This study aims to elucidate the chiral resolution of aromatic amino acids and their elution order using glycopeptides as chiral selectors through molecular docking [...] Read more.
An asymmetric synthesis is a favorable approach for obtaining enantiomerically pure substances, but racemic resolution remains an efficient strategy. This study aims to elucidate the chiral resolution of aromatic amino acids and their elution order using glycopeptides as chiral selectors through molecular docking analysis. Chiral separation experiments were conducted using Vancomycin as a chiral additive in the mobile phase (CMPA) at various concentrations, coupled with an achiral amino column as the stationary phase. The Autodock Vina 1.1.2 software was employed to perform molecular docking simulations between each enantiomer (ligand) and Vancomycin (receptor) to evaluate binding affinities, demonstrate enantiomeric resolution feasibility, and elucidate chiral recognition mechanisms. Utilizing Vancomycin as CMPA at a concentration of 1.5 mM enabled the separation of tryptophan enantiomers with a resolution of 3.98 and tyrosine enantiomers with a resolution of 2.97. However, a poor chiral resolution was observed for phenylalanine and phenylglycine. Molecular docking analysis was employed to elucidate the lack of separation and elution order for tryptophan and tyrosine enantiomers. By calculating the binding energy, docking results were found to be in good agreement with experimental findings, providing insights into the underlying mechanisms governing chiral recognition in this system and the interaction sites. This comprehensive approach clarifies the complex relationship between chiral discrimination and molecular architecture, offering valuable information for creating and improving chiral separation protocols. Full article
(This article belongs to the Special Issue Molecular Novelties in Chiral Enantioseparation and Discrimination)
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16 pages, 2563 KiB  
Article
Optimization of Liquid Crystalline Mixtures Enantioseparation on Polysaccharide-Based Chiral Stationary Phases by Reversed-Phase Chiral Liquid Chromatography
by Magdalena Urbańska
Int. J. Mol. Sci. 2024, 25(12), 6477; https://doi.org/10.3390/ijms25126477 - 12 Jun 2024
Cited by 1 | Viewed by 1126
Abstract
Enantioseparation of nineteen liquid crystalline racemic mixtures obtained based on (R,S)-2-octanol was studied in reversed-phase mode on an amylose tris(3-chloro-5-methylphenylcarbamate) (ReproSil Chiral-MIG) and a cellulose tris(3,5-dichlorophenylcarbamate) (ReproSil Chiral-MIC). These polysaccharide-based chiral stationary phase (CSP) columns for High-Performance Liquid Chromatography (HPLC) were highly effective [...] Read more.
Enantioseparation of nineteen liquid crystalline racemic mixtures obtained based on (R,S)-2-octanol was studied in reversed-phase mode on an amylose tris(3-chloro-5-methylphenylcarbamate) (ReproSil Chiral-MIG) and a cellulose tris(3,5-dichlorophenylcarbamate) (ReproSil Chiral-MIC). These polysaccharide-based chiral stationary phase (CSP) columns for High-Performance Liquid Chromatography (HPLC) were highly effective in recognizing isomers of minor structural differences. The mobile phase (MP), which consists of acetonitrile (ACN)/water (H2O) at different volume ratios, was used. The mobile phases were pumped at a flow rate of 0.3, 0.5, or 1 mL·min−1 with a column temperature of 25 °C, using a UV detector at 254 nm. The order of the elution was also determined. The chromatographic parameters, such as resolution (Rs), selectivity (α), and the number of theoretical plates, i.e., column efficiency (N), were determined. The polysaccharide-based CSP columns have unique advantages in separation technology, and this study has shown the potential usefulness of the CSP columns in separating liquid crystalline racemic mixtures belonging to the same homologous series. Full article
(This article belongs to the Special Issue Molecular Novelties in Chiral Enantioseparation and Discrimination)
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