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Special Issue "Symmetry and Asymmetry in Chromato-Mass-Spectrometry Analysis"

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

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 4288

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Special Issue Editor

Prof. Dr. Aleksey Konstantinovich Buryak

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Guest Editor

Frumkin Institute of Physical Chemistry and Electrochemistry of RAS, Moscow 119991, Russia
Interests: chromatography; chemical analysis; analytical method development; liquid chromatography; environmental analytical chemistry; method development; method validation; analytical chemistry instrumentation; mass spectrometry; high-performance liquid chromatography
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Special Issue Information

Dear Colleagues,

Chromatography, mass spectrometry, and their symbiosis—gas chromatography–mass spectrometry—are some of the most common analytical methods at the present.

According to the results of major international exhibitions, instruments that implement these methods account for up to 70% of all analytical instruments. An important place is occupied by the analysis of chiral (optically active) objects.

The most important consumer of chiral separations is pharmaceutical chemistry. The biological activity of different isomers often differs dramatically, which requires special synthesis, preparative separation, and, most importantly, analytical control over the content of each specific isomer.

This issue will be devoted to the use of chromatography, mass spectrometry, and gas chromatography-mass spectrometry in the analysis of chiral (optically active) objects. Such work began in the sixties of the last century with the work of E. Gil-Av with coworkers (1966). They succeeded in separating optical isomers for volatile amino acid derivatives using gas chromatography on a stationary liquid phase synthesized from chiral leucine. The next stage was the creation of chiral chromatography in the variant of ligand exchange chromatography proposed by V.A. Davankov (1968). The method made it possible to obtain pure substances with high resolution from unmodified racemic mixtures. Further improvement of methods for the separation of optical isomers made it possible to create various techniques for chromatographic and mass spectrometric analysis. The development of gas chromatography–mass spectrometry technology has made it possible to combine both methods and thereby increase the reliability of separation and identification of optical isomers.

We invite specialists working in the field of chemical synthesis, preparative isolation, and isomer-specific analysis to submit publications for a Special Issue on gas chromatography–mass spectrometric methods for the analysis of optical isomers.

Submit your paper and select the Journal “Symmetry” and the Special Issue “Symmetry and Asymmetry in Chromato-Mass-Spectrometry Analysis” via: MDPI submission system. Our papers will be published on a rolling basis and we will be pleased to receive your submission once you have finished it.

Prof. Dr. Aleksey Konstantinovich Buryak
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

chromatography
mass spectrometry (MS)
gas chromatography-mass spectrometry (GC-MS)
optically active objects
separation of optically isomers
chiral objects

Published Papers (3 papers)

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Research

14 pages, 2015 KiB

Open AccessFeature PaperArticle

Manifestation of Supramolecular Chirality during Adsorption on CsCuCl₃ and γ-Glycine Crystals

Ilya Zinovyev

Ekaterina Ermolaeva

Yuliya Sharafutdinova

and

Symmetry 2023, 15(2), 498; https://doi.org/10.3390/sym15020498 - 13 Feb 2023

Cited by 3 | Viewed by 778

Abstract

The chirality of biopolymers and its emergence from the racemic prebiotic world is one of the key mysteries of science. There are many versions on how the total chiral balance breaking occurred, but they all face an insoluble challenge—the impossibility of a total shift of the chiral balance towards the formation of biopolymers based only on D-sugars and L-amino acids. A possible solution to this problem lies in the asymmetric autocatalysis on chiral crystals. Since the reaction is heterogeneous, it is important to study the features of adsorption on the surface of crystals. In this paper, the adsorption of limonene, α-pinene, and menthol enantiomers on γ-glycine and CsCuCl₃ crystals was studied. Single-crystal X-ray crystallography, SEM, and porosimetry were used as auxiliary methods. The t-test was used to determine the reliability of chiral recognition. It was shown that both crystals were capable of chiral recognition at high coverages. The mechanism of supramolecular chiral recognition was identical to that of the chiral crystals studied previously. However, neither γ-glycine nor CsCuCl₃ showed chiral recognition with respect to all enantiomers. In fact, γ-glycine crystals showed recognition for limonene enantiomers, and very high recognition in the case of menthol enantiomers. CsCuCl₃ crystals showed the capability to recognize enantiomers of α-pinenes only. This led to the conclusion that the recognition of enantiomers by a supramolecular chiral surface is not universal. Full article

(This article belongs to the Special Issue Symmetry and Asymmetry in Chromato-Mass-Spectrometry Analysis)

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15 pages, 5383 KiB

Open AccessFeature PaperArticle

Enantioseparation of β-Blockers Using Silica-Immobilised Eremomycin Derivatives as Chiral Stationary Phases in HPLC

and

Symmetry 2023, 15(2), 373; https://doi.org/10.3390/sym15020373 - 30 Jan 2023

Cited by 1 | Viewed by 862

Abstract

The regularities of chromatographic retention and separation enantioselectivity of the selected β-blockers (propranolol, pindolol, alprenolol, atenolol, oxprenalol, metoprolol, clenbuterol, sotalol, pronethalol, salbutamol, and labetalol) were studied with eight chiral stationary phases (CSPs) in polar ionic mode (PIM) elution system. A range of novel CSPs was prepared by immobilisation of macrocyclic glycopeptide antibiotic eremomycin (E-CSP); structurally related antibiotics chloreremomycin (Chloro-E-CSP) and semi-synthetic oritavancin (O-CSP); and five eremomycin derivatives including amide- (Amide-E-CSP), adamantyl-2-amide- (Adamantylamide-E-CSP), eremomycin aglycon (EAg-CSP), eremosaminyl eremomycin aglycon (EEA-CSP), and des-eremosamynyl eremomycin (DEE-CSP) onto microspherical silica (Kromasil, particle size 5 micron, pore size 11 nm). The effect of different functional groups in eremomycin structure on chiral recognition of β-blockers was studied. The original E-CSP revealed moderate enantioseparation for all studied β-blockers. The presence of a free carboxylic group in a chiral selector molecule is found to be critical for the general retention of enantiomers as no separation enantioselectivity was recorded for Amide-E-CSP and Adamantyl-E-CSP. Modification of the aromatic system of eremomycin by the introduction of a chloro- substituent in the aromatic ring (Chloro-E-CSP) or a hydrophobic 4’-chlorobiphenylmethyl substituent to the disaccharide sugar residue (O-CSP) resulted in decreased enantioselectivity. The best enantioseparation of β-blockers was obtained for CSPs with eremosaminyl eremomycin aglycon and des-eremosamynyl eremomycin as chiral selectors. Full article

(This article belongs to the Special Issue Symmetry and Asymmetry in Chromato-Mass-Spectrometry Analysis)

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18 pages, 3292 KiB

Open AccessArticle

Calculations of the Thermodynamic Characteristics and Physicochemical Properties of Symmetric and Asymmetric Isomeric Compounds for Identification in Chromatography-Mass Spectrometry

and

Symmetry 2021, 13(9), 1681; https://doi.org/10.3390/sym13091681 - 12 Sep 2021

Cited by 2 | Viewed by 1435

Abstract

A combination of theoretical and experimental approaches was applied to determine the chromatographic rules of isomeric compounds’ behavior for preliminary identification. In gas chromatography-mass spectrometry (GC-MS), identification is performed by spectra matching, however, difficulties arise with isomeric compounds, which cannot be distinguished from each other without additional information. The thermodynamic characteristics of the adsorption of symmetric and asymmetric isomers of chlorophenylphenols, dimethoxybiphenyls, tri- and tetrachlorobiphenyls were determined using molecular statistical calculations. By-products in the chlorination of 4-hydroxybiphenyl were identified: 4-hydroxy-2,3′- and 3,2′-dichlorobiphenyls, 4-hydroxy-3,5,2′- and 2,3,6-trichlorobiphenyls. A developed theoretical approach was applied to predict the retention order of tri- and tetra-chlorobiphenyls. The GC-MS data and molecular statistical calculations made it possible to determine the main products of methoxybenzene dimerization as well as identify impurities. Thermodynamic parameters were received to describe the unusual retention behavior of epimers in reversed-phase high-performance liquid chromatography. Molecular descriptors were calculated to determine correlation with retention of both structural isomers and epimers. Descriptor combining surface area and partial charge information turned out to be useful in evaluating retention order for isomers. Full article

(This article belongs to the Special Issue Symmetry and Asymmetry in Chromato-Mass-Spectrometry Analysis)

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