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Special Issue "Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Analytical Chemistry".

Deadline for manuscript submissions: 31 January 2019

Special Issue Editors

Guest Editor
Prof. Dr. Maria Elizabeth Tiritan

1. Institute of Research and Advanced Training in Health Sciences and Technologies, Cooperativa de Ensino Superior Politécnico e Universitário (CESPU), Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal
2. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
3. Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR/CIMAR), Universidade do Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal Email: elizabeth.tiritan@iucs.cespu.pt
Website | E-Mail
Interests: drug discovery; chiral bioactive compounds; enantiomeric separation; chiral stationary phases and chiral analyses
Guest Editor
Prof. Dr. Madalena Pinto

1. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2. Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR/CIMAR), Universidade do Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal
Website | E-Mail
Interests: drug discovery; chiral bioactive compounds; chiral recognition and chiral analyses
Guest Editor
Assist. Prof. Carla Sofia Garcia Fernandes

1. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2. Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR/CIMAR), Universidade do Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal
Website | E-Mail
Interests: drug discovery; chirality; development of new chiral stationary phases; chiral recognition and chiral analyses

Special Issue Information

Dear Colleagues,

The importance of developing analytic methods and the search for bioactive/behaviors of enantiomers is well recognized by academics and industries. Currently, the demand for efficient methodologies to obtain chiral bioactive compounds with a high degree of enantiomeric purity requires continuous advances in enantioselective synthesis, chiral analyses, preparative enantioseparation, and chiral recognition studies.

The main aims of the present Special Issue on "Enantioselective Synthesis, Enantiomeric Separations, and Chiral Recognition" include both fundamental studies and applications in a multidisciplinary research field that enrolls chiral compounds in general. Contributions to this issue, both in the form of original research or review articles, have the broad scope to illustrate recent and future trends in methodologies to obtain enantiomers in a highly enantiomeric pure form, and studies of chiral recognition in enantiomeric separations as well as in pharmacodynamic, pharmacokinetic, and toxicological events.

Innovative approaches in the field of enantioselective synthesis, chiral analyses by chromatographic methods, and the determination of enantiomeric purity and chiral recognition studies—both in enantioseparation and in biological systems—are particularly welcome.

Prof. Dr. Maria Elizabeth Tiritan
Prof. Dr. Madalena Pinto
Prof. Dr. Carla Sofia Garcia Fernandes
Guest Editors

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 papers will be 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. Molecules 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 1800 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

  • enantioseparation
  • chiral chromatography
  • chiral recognition
  • chiral analyses
  • enantioselective synthesis

Published Papers (3 papers)

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Research

Open AccessArticle Chiral Separation of the Phenylglycinol Enantiomers by Stripping Crystallization
Molecules 2018, 23(11), 2901; https://doi.org/10.3390/molecules23112901
Received: 8 October 2018 / Revised: 4 November 2018 / Accepted: 5 November 2018 / Published: 7 November 2018
PDF Full-text (1044 KB) | HTML Full-text | XML Full-text
Abstract
Stripping crystallization (SC) is introduced in this work for chiral purification of R-phenylglycinol from the enantiomer mixture with an initial concentration ranging from 0.90 to 0.97. As opposed to the solid–liquid transformation in melt crystallization, the three-phase transformation occurs in SC at
[...] Read more.
Stripping crystallization (SC) is introduced in this work for chiral purification of R-phenylglycinol from the enantiomer mixture with an initial concentration ranging from 0.90 to 0.97. As opposed to the solid–liquid transformation in melt crystallization, the three-phase transformation occurs in SC at low pressures during the cooling process. SC combines melt crystallization and vaporization to produce a crystalline product and mixture vapor from a mixture melt due to the three-phase transformation. Thermodynamic calculations were applied to determine the operating pressure for the three-phase transformation during the cooling process in the SC experiments. To consider the possible deviations between the calculated and the actual three-phase transformation conditions, the product purity and the recovery ratio of R-phenylglycinol were investigated within a range of operating pressures during the cooling process. Full article
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Open AccessArticle Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs
Molecules 2018, 23(10), 2680; https://doi.org/10.3390/molecules23102680
Received: 15 September 2018 / Revised: 4 October 2018 / Accepted: 15 October 2018 / Published: 18 October 2018
PDF Full-text (1628 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The distinct pharmacodynamic and pharmacokinetic properties of enantiopure sulfoxide drugs have stimulated us to systematically investigate their chiral separation, stereochemical assignment, and chiral recognition mechanism. Herein, four clinically widely-used sulfoxide drugs were chosen and optically resolved on various chiral stationary phases (CSPs). Theoretical
[...] Read more.
The distinct pharmacodynamic and pharmacokinetic properties of enantiopure sulfoxide drugs have stimulated us to systematically investigate their chiral separation, stereochemical assignment, and chiral recognition mechanism. Herein, four clinically widely-used sulfoxide drugs were chosen and optically resolved on various chiral stationary phases (CSPs). Theoretical simulations including electronic circular dichroism (ECD) calculation and molecular docking were adopted to assign the stereochemistry and reveal the underlying chiral recognition mechanism. Our results showed that the sequence of calculated mean binding energies between each pair of enantiomers and CSP matched exactly with experimentally observed enantiomeric elution order (EEO). It was also found that the length of hydrogen bond might contribute dominantly the interaction between two enantiomers and CSP. We hope our study could provide a fresh perspective to explore the stereochemistry and chiral recognition mechanism of chiral drugs. Full article
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Graphical abstract

Open AccessArticle Improved Enantioselectivity for Atenolol Employing Pivot Based Molecular Imprinting
Molecules 2018, 23(8), 1875; https://doi.org/10.3390/molecules23081875
Received: 3 June 2018 / Revised: 20 July 2018 / Accepted: 26 July 2018 / Published: 27 July 2018
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Abstract
In the last few decades, molecular imprinting technology went through a spectacular evolution becoming a well-established tool for the synthesis of highly selective biomimetic molecular recognition platforms. Nevertheless, there is still room for advancement in the molecular imprinting of highly polar chiral compounds.
[...] Read more.
In the last few decades, molecular imprinting technology went through a spectacular evolution becoming a well-established tool for the synthesis of highly selective biomimetic molecular recognition platforms. Nevertheless, there is still room for advancement in the molecular imprinting of highly polar chiral compounds. The aim of the present work was to investigate the favorable kosmotropic effect of a ternary complex involving a polar chiral template (eutomer of atenolol) and a functional monomer, bridged by a central metal ion through well-defined, spatially directional coordinate bonds. The efficiency of the chiral molecular recognition was systematically assessed on polymers obtained both by non-covalent and metal-mediated molecular imprinting. The influence on the chromatographic retention and enantioselectivity of different experimental variables (functional monomers, cross-linkers, chaotropic agents, metal ions, porogenic systems, etc.) were studied on both slurry packed and monolithic HPLC columns. Deliberate changes in the imprinting and rebinding (chromatographic) processes, along with additional thermodynamic studies shed light on the particularities of the molecular recognition mechanism. The best performing polymer in terms of enantioselectivity (α = 1.60) was achieved using 4-vinyl pyridine as functional monomer and secondary ligand for the Co(II)-mediated imprinting of S-atenolol in the presence of EDMA as cross-linker in a porogenic mixture of [BMIM][BF4]:DMF:DMSO = 10:1:5, v/v/v. Full article
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