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Chiral Structures, Preparation and Separation of Optically Active Compounds
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Chiral Structures, Preparation and Separation of Optically Active Compounds

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: closed (30 June 2023) | Viewed by 6288

Special Issue Editor

Prof. Dr. Elemér Fogassy

E-Mail Website
Guest Editor
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
Interests: resolution; enantiomers; diastereomers; racemate and conglomerate behaviour; memory of enantiomers; eutectic composition
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

A significant proportion of commercially available drugs are optically active compounds. However, in many cases, the enantiomers have different or even opposite therapeutic effects, so there is a growing demand for the preparation of pure enantiomers from both a scientific and pharmaceutical point of view. Despite unprecedented advances in enantioselective syntheses and various separation techniques, the large-scale production of enantiomerically pure materials required by the pharmaceutical and pesticide industries is still heavily dependent on the separation and decomposition of diastereomers, the separation of the resolving agent and the purification of the enantiomers.

This Special Issue welcomes original research papers and reviews on the preparation of pure enantiomers. Furthermore, we provide an overview of new advances in the development and application of “traditional” or new methods and techniques in the resolution processes.

As chiral compounds are part of our daily lives, a deeper understanding of the observations, experiences and connections gained during their preparation may be of interest to all chemists.

Prof. Dr. Elemér Fogassy
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.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • resolution
  • selective syntheses
  • optically active compounds
  • flow chemistry
  • new methods for separation of enantiomers
  • optimization of conditions of the resolution
  • advanced techniques

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Published Papers (2 papers)

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Research

14 pages, 1655 KiB  
Article
Bio-Approach for Obtaining Enantiomerically Pure Clopidogrel with the Use of Ionic Liquids
by Joanna Chałupka, Adam Sikora, Marta Ziegler-Borowska and Michał Piotr Marszałł
Int. J. Mol. Sci. 2023, 24(13), 11124; https://doi.org/10.3390/ijms241311124 - 5 Jul 2023
Viewed by 2463
Abstract
Clopidogrel is a chiral compound widely used as an antiplatelet medication that lowers the risk of blood clots, strokes, and heart attacks. The main aim of the study presented herein was to obtain (S)-clopidogrel, which is commercially available in treatments, via [...] Read more.
Clopidogrel is a chiral compound widely used as an antiplatelet medication that lowers the risk of blood clots, strokes, and heart attacks. The main aim of the study presented herein was to obtain (S)-clopidogrel, which is commercially available in treatments, via the kinetic resolution of racemic clopidogrel carboxylic acid with the use of lipase from Candida rugosa and a two-phase reaction medium containing an ionic liquid. For this purpose, the enantioselective biotransformation of clopidogrel carboxylic acid and chiral chromatographic separation with the use of a UPLC-MS/MS system were optimized. The best kinetic resolution parameters were obtained by using a catalytic system containing lipase from Candida rugosa OF as a biocatalyst, cyclohexane and [EMIM][BF4] as a two-phase reaction medium, and methanol as an acyl acceptor. The enantiomeric excess of the product was eep = 94.21% ± 1.07 and the conversion was c = 49.60% ± 0.57%, whereas the enantioselectivity was E = 113.40 ± 1.29. The performed study proved the possibility of obtaining (S)-clopidogrel with the use of lipase as a biocatalyst and a two-phase reaction medium containing an ionic liquid, which is in parallel with green chemistry methodology and does not require environmentally harmful conditions. Full article
(This article belongs to the Special Issue Chiral Structures, Preparation and Separation of Optically Active Compounds)
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15 pages, 2225 KiB  
Article
Enantioselective Human Serum Albumin Binding of Apremilast: Liquid Chromatographic, Fluorescence and Molecular Docking Study
by Gergely Dombi, Péter Horváth, Béla Fiser, Arash Mirzahosseini, Máté Dobó, Zoltán-István Szabó and Gergő Tóth
Int. J. Mol. Sci. 2023, 24(3), 2168; https://doi.org/10.3390/ijms24032168 - 21 Jan 2023
Cited by 11 | Viewed by 3126
Abstract
The interaction between human serum albumin (HSA) and apremilast (APR), a novel antipsoriatic drug, was characterized by multimodal analytical techniques including high-performance liquid chromatography (HPLC), fluorescence spectroscopy and molecular docking for the first time. Using an HSA chiral stationary phase, the APR enantiomers [...] Read more.
The interaction between human serum albumin (HSA) and apremilast (APR), a novel antipsoriatic drug, was characterized by multimodal analytical techniques including high-performance liquid chromatography (HPLC), fluorescence spectroscopy and molecular docking for the first time. Using an HSA chiral stationary phase, the APR enantiomers were well separated, indicating enantioselective binding between the protein and the analytes. The influence of chromatographic parameters—type and concentration of the organic modifier, buffer type, pH, ionic strength of the mobile phase, flow rate and column temperature—on the chromatographic responses (retention factor and selectivity) was analyzed in detail. The results revealed that the eutomer S-APR bound to the protein to a greater extent than the antipode. The classical van ’t Hoff method was applied for thermodynamic analysis, which indicated that the enantioseparation was enthalpy-controlled. The stability constants of the protein–enantiomer complexes, determined by fluorescence spectroscopy, were in accordance with the elution order observed in HPLC (KR-APR-HSA = 6.45 × 103 M−1, KS-APR-HSA = 1.04 × 104 M−1), showing that, indeed, the later-eluting S-APR displayed a stronger binding with HSA. Molecular docking was applied to study and analyze the interactions between HSA and the APR enantiomers at the atomic level. It was revealed that the most favored APR binding occurred at the border between domains I and II of HSA, and secondary interactions were responsible for the different binding strengths of the enantiomers. Full article
(This article belongs to the Special Issue Chiral Structures, Preparation and Separation of Optically Active Compounds)
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