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Symmetry
Special Issues
Chiral Molecules - Production and Biological Properties
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Chiral Molecules - Production and Biological Properties

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 March 2021) | Viewed by 9080

Special Issue Editor

Prof. Dr. Witold Gładkowski

E-Mail Website
Guest Editor
Department of Chemistry, Wrocław University of Environmental and Life Science, Wrocław, Poland
Interests: biotransformations of organic compounds by whole cells; chemoenzymatic synthesis of optically active lactones with biological activity; determination of absolute configurations of optically active compounds; enzymatic modifications of phospholipids; analytical and spectroscopic methods to establish the structure of new compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Constituents of living organisms are predominantly built up from chiral building blocks: e.g. L-amino acids and D-carbohydrates. Life processes therefore involve stereochemically defined molecules. Searching for new biologically active compounds both enantiomers with defined configurations of stereogenic centers should be studied separately to assess the relevance of stereoisomerism on their properties. Chiral molecules can be built by several methods that include chemical synthesis from natural chiral precursors, asymmetric synthesis using chemical chiral catalysts as well as biocatalysts – isolated free or immobilized enzymes or whole-cell biocatalysts.

For this Special Issue, contributions from new aspects of production of chiral molecules and effect of configuration of their stereogenic centers on the biological activity are welcomed.

Prof. Dr. Witold Gładkowski
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. Symmetry is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). 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

  • chiral molecules
  • configuration of chiral centers
  • biological activity
  • asymmetric synthesis
  • biocatalysts
  • enzymes

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Published Papers (3 papers)

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Research

14 pages, 1466 KiB  
Article
Can an Intermediate Rate of Nitrogen Inversion Affect Drug Efficacy?
by Raphael R. Steimbach, Gergely Tihanyi, Magalie N. E. Géraldy, Alicja Wzorek, Aubry K. Miller and Karel D. Klika
Symmetry 2021, 13(9), 1753; https://doi.org/10.3390/sym13091753 - 20 Sep 2021
Cited by 1 | Viewed by 2412
Abstract
Nitrogen-inversion rates and diffusion coefficients were measured using 1H NMR for 14 drug-like molecules. The slow nitrogen-inversion rates interconverting the enantiomers of these molecules lay within a postulated intermediate range in terms of their ability to bind to proteins bounded by diffusion [...] Read more.
Nitrogen-inversion rates and diffusion coefficients were measured using 1H NMR for 14 drug-like molecules. The slow nitrogen-inversion rates interconverting the enantiomers of these molecules lay within a postulated intermediate range in terms of their ability to bind to proteins bounded by diffusion constraints, potentially affecting the availability, hence efficacy, of these compounds if they were utilized as drugs. The postulated intermediate range is based on a capture-volume concept, whereby the nitrogen inversion during the time a ligand takes to pass through a volume surrounding the protein binding site, as calculated by the diffusion rate, determines if it will influence ligand binding to the protein. In the systems examined here, the measured nitrogen-inversion rates and the times required to traverse the capture volume differed by a few orders of magnitude. Potentially more consequential are intermediate nitrogen-inversion rates in epimeric cases—since the energies of the interconverting species are unequal, a heavy bias against the eutomer might occur. The implications of an intermediate nitrogen-inversion rate are significant for in silico drug design, drug efficacy, molecular modeling of drug–protein binding, pharmacokinetics, drug enantiomer evaluation, etc. Due consideration of the process should thus be taken into account for drug development directions and in vitro evaluation. Full article
(This article belongs to the Special Issue Chiral Molecules - Production and Biological Properties)
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18 pages, 1340 KiB  
Article
Flurbiprofen: A Study of the Behavior of the Scalemate by Chromatography, Sublimation, and NMR
by Magdalena Kwiatkowska, Alicja Wzorek, Anna Kolbus, Mariusz Urbaniak, Jianlin Han, Vadim A. Soloshonok and Karel D. Klika
Symmetry 2021, 13(4), 543; https://doi.org/10.3390/sym13040543 - 26 Mar 2021
Cited by 9 | Viewed by 2958
Abstract
2-(2-Fluoro-4-biphenyl) propionic acid (flurbiprofen), from the phenylalkanoic acid family of nonsteroidal anti-inflammatory drugs (NSAID’s), is currently on the pharmaceutical market as a racemate. This racemic compound was tested for its propensity to undergo the self-disproportionation of enantiomers (SDE) phenomenon by various forms of [...] Read more.
2-(2-Fluoro-4-biphenyl) propionic acid (flurbiprofen), from the phenylalkanoic acid family of nonsteroidal anti-inflammatory drugs (NSAID’s), is currently on the pharmaceutical market as a racemate. This racemic compound was tested for its propensity to undergo the self-disproportionation of enantiomers (SDE) phenomenon by various forms of chromatography (SDEvC), such as routine gravity-driven column chromatography, medium-pressure liquid chromatography (MPLC), preparative thin-layer chromatography (PTLC), and size-exclusion chromatography (SEC), as well as by sublimation (SDEvS). Furthermore, examination by nuclear magnetic resonance (NMR) in various solvents found that flurbiprofen exhibited the phenomenon of self-induced diastereomeric anisochronism (SIDA). By measurement of the diffusion coefficient (D), the longitudinal relaxation time (T1), and the transverse relaxation time (T2) using NMR, as well as by electrospray ionization-mass spectrometry (ESI-MS) examinations, the preferred intermolecular association was found to be solvent dependent, e.g., heterochiral association was preferred in toluene, while homochiral association was preferred in more polar solvents. This study also attempted, unsuccessfully, to correlate the NMR measurements of flurbiprofen with chromatographic outcomes for the rationalization and prediction of chromatographic results based on NMR measurements. Because the intermolecular hydrogen bonding of the acid groups in flurbiprofen overwhelmingly predominates over other intermolecular interactions, flurbiprofen seemed to represent a good test case for this idea. The behavior of scalemic samples of flurbiprofen is important, as, although it is currently dispensed as a racemate, clinical applications of the R enantiomer have been investigated. SDEvC and SDEvS both have ramifications for the preparation, handling, and storage of enantioenriched flurbiprofen, and this concern applies to other chiral drugs as well. Full article
(This article belongs to the Special Issue Chiral Molecules - Production and Biological Properties)
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14 pages, 1323 KiB  
Article
Half-Preparative Scale Synthesis of (S)-1-Phenylethane-1,2-Diol as a Result of 2-Phenylethanol Hydroxylation with Aspergillus niger (IAFB 2301) Assistance
by Beata Szmigiel-Merena, Małgorzata Brzezińska-Rodak, Magdalena Klimek-Ochab, Paulina Majewska and Ewa Żymańczyk-Duda
Symmetry 2020, 12(6), 989; https://doi.org/10.3390/sym12060989 - 10 Jun 2020
Cited by 1 | Viewed by 3213
Abstract
Aspergillus niger (IAFB 2301) was employed for bioconversions of 2-phenylethanol as an immobilized or free mycelium and also as a spore suspension. Experiments were conducted on laboratory and half-preparative scale (bioreactor New Brunswick Scientific, BioFlo Model C32). Thus, A. niger applied as free [...] Read more.
Aspergillus niger (IAFB 2301) was employed for bioconversions of 2-phenylethanol as an immobilized or free mycelium and also as a spore suspension. Experiments were conducted on laboratory and half-preparative scale (bioreactor New Brunswick Scientific, BioFlo Model C32). Thus, A. niger applied as free mycelium, depending on the outcome, supported formation of the mixture of 4-hydroxyphenylacetic acid and hydroxytyrosol (final concentration of 13.8 mg/L and 3.7% efficiency) or 4-hydroxyphenylacetic acid, as single product (final concentration of 140 mg/L and 18% efficiency). In case of scaling experiments conducted with flow and batch reactors, accordingly, the following results were achieved: 1. mixture of antioxidants 4-hydroxyphenylacetic acid and hydroxytyrosol formed with final concentration of 76 mg/L and 10% efficiency (simplified flow system and immobilized mycelium); 2. (S)-1-phenylethane-1,2-diol synthesized with a final concentration of 447 mg/L and 65% (1.3 L batch reactor). Full article
(This article belongs to the Special Issue Chiral Molecules - Production and Biological Properties)
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