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Special Issue "Chirality in Health and Environment: Recent developments"

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

Deadline for manuscript submissions: closed (31 December 2017)

Special Issue Editors

Guest Editor
Prof. Dr. Madalena M. M. Pinto

Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências, Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira 228, 4050-313, Porto, Portugal; Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR/CIMAR), Universidade do Porto, Rua dos Bragas 289, 4050-123 Porto, Portugal
Website | E-Mail
Interests: medicinal chemistry; drug discovery and drug design; synthesis and bioenantioselectivity studies of chiral bioactive compounds, as well as studies of structure-activity and structure-properties relationships; molecular recognition-artificial receptors as new chiral stationary phases for HPLC
Guest Editor
Assist. Prof. Carla Fernandes

CIIMAR and Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal
Website | E-Mail
Interests: design and synthesis of chiral compounds with potential biological activity as well as chiral stationary phases for liquid chromatography; analytical and preparative enantiomeric separation of racemic mixtures and studies of chiral recognition mechanisms

Special Issue Information

Dear Colleagues,

It is well known that the environment and human health are directly connected in many ways, with chirality interrelating both areas; why is this?

Human beings, as well as many biological molecules, are chiral, including numerous natural products and several substances created by man, interacting with the environment.

Life on Earth, as we know it, depends on chiral molecules, and the recent discovery of an astronomical chiral molecule, propylene oxide, representative of the earliest stage of solar system evolution, makes us believe that, as far as the subject matter of chirality is concerned, “the sky is the limit”!

This progress results of several inter/transdisciplinary fields from, among others, physics, chemistry and biology, which are very challenging for researchers involved in these areas.

This Special Issue is intended to highlight and update the state-of-the-art and recent progress in several topics, namely:

  • Chirality in daily life: Chemical communication among humans; importance of odor (flavors and fragrances; perception of chiral odorants) and taste (artificial sweeteners); chiral cosmetics and personal care products.
  • Chirality in chemical and pharmaceutical industries.
  • Chiral drugs/pharmaceuticals.
  • Chirality of molecules from nature.
  • Chiral xenobiotics in marine and terrestrial ecosystems.
  • Chiral analysis.

Prof. Madalena Pinto
Assist. Prof. Carla 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

  • Chirality
  • Chiral molecules
  • Health
  • Environment

Published Papers (4 papers)

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Research

Open AccessArticle Enantiomeric Resolution and Docking Studies of Chiral Xanthonic Derivatives on Chirobiotic Columns
Molecules 2018, 23(1), 142; doi:10.3390/molecules23010142
Received: 29 November 2017 / Revised: 6 January 2018 / Accepted: 8 January 2018 / Published: 11 January 2018
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Abstract
A systematic study of enantioresolution of a library of xanthonic derivatives, prepared “in-house”, was successfully carried out with four commercially available macrocyclic glycopeptide-based columns, namely ChirobioticTM T, ChirobioticTM R, ChirobioticTM V and ChirobioticTM TAG. Evaluation was conducted in multimodal
[...] Read more.
A systematic study of enantioresolution of a library of xanthonic derivatives, prepared “in-house”, was successfully carried out with four commercially available macrocyclic glycopeptide-based columns, namely ChirobioticTM T, ChirobioticTM R, ChirobioticTM V and ChirobioticTM TAG. Evaluation was conducted in multimodal elution conditions: normal-phase, polar organic, polar ionic and reversed-phase. The effects of the mobile phase composition, the percentage of organic modifier, the pH of the mobile phase, the nature and concentration of different mobile phase additives on the chromatographic parameters are discussed. ChirobioticTM T and ChirobioticTM V, under normal-phase and reversed-phase modes, respectively, presented the best chromatographic parameters. Considering the importance of understanding the chiral recognition mechanisms associated with the chromatographic enantioresolution, and the scarce data available for macrocyclic glycopeptide-based columns, computational studies by molecular docking were also carried out. Full article
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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Open AccessArticle Discrimination of Stereoisomers by Their Enantioselective Interactions with Chiral Cholesterol-Containing Membranes
Molecules 2018, 23(1), 49; doi:10.3390/molecules23010049
Received: 30 November 2017 / Revised: 22 December 2017 / Accepted: 22 December 2017 / Published: 25 December 2017
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Abstract
Discrimination between enantiomers is an important subject in medicinal and biological chemistry because they exhibit markedly different bioactivity and toxicity. Although stereoisomers should vary in the mechanistic interactions with chiral targets, their discrimination associated with the mode of action on membrane lipids is
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Discrimination between enantiomers is an important subject in medicinal and biological chemistry because they exhibit markedly different bioactivity and toxicity. Although stereoisomers should vary in the mechanistic interactions with chiral targets, their discrimination associated with the mode of action on membrane lipids is scarce. The aim of this study is to reveal whether enantiomers selectively act on chiral lipid membranes. Different classes of stereoisomers were subjected at 5–200 μM to reactions with biomimetic phospholipid membranes containing ~40 mol % cholesterol to endow the lipid bilayers with chirality and their membrane interactions were comparatively evaluated by measuring fluorescence polarization. All of the tested compounds interacted with cholesterol-containing membranes to modify their physicochemical property with different potencies between enantiomers, correlating to those of their experimental and clinical effects. The rank order of membrane interactivity was reversed by changing cholesterol to C3-epimeric α-cholesterol. The same selectivity was also obtained from membranes prepared with 5α-cholestan-3β-ol and 5β-cholestan-3α-ol diastereomers. The opposite configuration allows molecules to interact with chiral sterol-containing membranes enantioselectively, and the specific β configuration of cholesterol’s 3-hydroxyl group is responsible for such selectivity. The enantioselective membrane interaction has medicinal implications for the characterization of the stereostructures with higher bioactivity and lower toxicity. Full article
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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Open AccessCommunication Chiral Symmetry Breaking in Magnetoelectrochemical Etching with Chloride Additives
Molecules 2018, 23(1), 19; doi:10.3390/molecules23010019
Received: 29 November 2017 / Revised: 19 December 2017 / Accepted: 20 December 2017 / Published: 22 December 2017
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Abstract
Magnetoelectrolysis (electrolysis under magnetic fields) produces chiral surfaces on metal thin films, which can recognize the enantiomers of amino acids. Here, the chiral surface formation on copper films is reported in magnetoelectrochemical etching (MEE) at 5T with chloride additives. In the absence of
[...] Read more.
Magnetoelectrolysis (electrolysis under magnetic fields) produces chiral surfaces on metal thin films, which can recognize the enantiomers of amino acids. Here, the chiral surface formation on copper films is reported in magnetoelectrochemical etching (MEE) at 5T with chloride additives. In the absence of additives, the surface chirality signs of MEE films depended on the magnetic field polarity. On the contrary, the MEE films prepared with the additives exhibited only d-activity in both magnetic field polarities. This result implies that the specific adsorption of chloride additives induces the chiral symmetry breaking for the magnetic field polarity. Full article
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
Figures

Open AccessArticle Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates
Molecules 2017, 22(9), 1410; doi:10.3390/molecules22091410
Received: 14 July 2017 / Revised: 23 August 2017 / Accepted: 24 August 2017 / Published: 25 August 2017
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Abstract
Enantiomeric-enriched ferrocene-modified pyrazoles were synthesized via the reaction of the ferrocene alcohol, (S)-FcCH(OH)CH3 (Fc = ferrocenyl), with various pyrazoles in acidic conditions at room temperature within several minutes. X-ray structural data for racemic (R,S)-1N-(3,5-dimethyl
[...] Read more.
Enantiomeric-enriched ferrocene-modified pyrazoles were synthesized via the reaction of the ferrocene alcohol, (S)-FcCH(OH)CH3 (Fc = ferrocenyl), with various pyrazoles in acidic conditions at room temperature within several minutes. X-ray structural data for racemic (R,S)-1N-(3,5-dimethyl pyrazolyl)ethyl ferrocene (1) and its (S)-enantiomer (S)-1 were determined. A series of racemic pyrazolylalkyl ferrocenes was separated into enantiomers by analytical HPLC on β- and γ-cyclodextrins (CD) chiral stationary phases. The quantum chemical calculations of interaction energies of β-CD were carried out for both (R)- and (S)-enantiomers. A high correlation between experimental HPLC data and calculated interaction energies values was obtained. Full article
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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