Separation of Enantiomers Using Gas Chromatography: Application in Forensic Toxicology, Food and Environmental Analysis

Ribeiro, Cláudia; Gonçalves, Ricardo; Tiritan, Maria Elizabeth

doi:10.1080/10408347.2020.1777522

Cited by 24 publications

(17 citation statements)

References 151 publications

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“…Some of the applications are described in detail in recent review papers and book chapters on this topic. 1056,1135 5.1.2. High-Performance Liquid Chromatography.…”

Section: Gas Chromatographymentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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“…Some of the applications are described in detail in recent review papers and book chapters on this topic. 1056,1135 5.1.2. High-Performance Liquid Chromatography.…”

Section: Gas Chromatographymentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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“…The extreme broad chiral selectivity spectra of the CD molecules make them the most popular chiral selectivity agents using capillary columns in GC [14,16,24,[31][32][33][34], CE [11,13,15,17,22,25,[26][27][28]35], and SFC [36]. CDs can separate enantiomers with any functional groups.…”

Section: Chiral Selectivity Of Cdsmentioning

confidence: 99%

Cyclodextrins as Dominant Chiral Selective Agents in the Capillary Separation Techniques

Juvancz

Bodáné-Kendrovics

Szente

et al. 2021

Period. Polytech. Chem. Eng.

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This review paper shows the dominant role of the cyclodextrins in the chiral separations using capillary columns (GC, SFC, CE). The cyclodextrins (CDs) have extremely broad chiral selectivity spectra because they have several different chiral recognition sites in various arrangements and various interaction modes. Their chiral selectivity features can further improve with their various substitutions. Their selectivities are moderate therefore they need high efficiency separations (capillary columns) for good chiral resolutions. The shape selectivity of cyclodextrins is also shown with non-chiral isomers too. The utility of the cyclodextrins is demonstrated with several examples based on the personal observations of authors and critical review of literature. The theoretical backgrounds of their chiral recognitions (e.g. H-bond interaction, inclusion, induced fit) are discussed in depth. This paper is not application oriented but is dealing with mostly on the physical and chemical background of separations using CDs.

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“…Regarding enantioselective methods for PAS analysis, liquid chromatography (LC) and gas chromatography (GC) are among the most used [9,14] for water matrices such as wastewaters and surface waters [7,15,16]. The enantioseparation can be done by a direct method using chiral stationary phases [9,17] or an indirect method through formation of diastereomers by reaction with an enantiomerically pure reagent [7,16].…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters

et al. 2021

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Determination of psychoactive substances (PAS) and/or their metabolites in surface waters is crucial for environmental risk assessment, and disclosure of their enantiomeric fractions (EF) allows discrimination between consumption, direct disposal, and synthesis pathways. The aim of this study was to develop and validate an indirect method by gas chromatography coupled to mass spectrometry (GC–MS) based on derivatization using (R)-(−)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride as chiral derivatization reagent, for enantiomeric quantification of amphetamine (AMP), methamphetamine (MAMP), 3,4-methylenedioxymethamphetamine (MDMA), norketamine, buphedrone (BPD), butylone, 3,4-dimethylmethcathinone (3,4-DMMC), 3-methylmethcathinone, and quantification of 1-benzylpiperazine and 1-(4-metoxyphenyl)-piperazine. The method allowed to evaluate the occurrence, spatial distribution, and the EF of the target chiral PAS in Portuguese surface waters and in effluents from 2 wastewater treatment plants (WWTP). For that, water samples were pre-concentrated by solid phase extraction using OASIS® MCX cartridges, derivatized and further analyzed by GC–MS. Both enantiomers of AMP, (R)-MDMA, (S)-MAMP, and the first eluted enantiomer of BPD (configuration not assigned) were found in surface waters, while effluent samples showed both enantiomers of MDMA, (S)-MAMP, (R)-AMP, and the first eluted enantiomer of BPD and 3,4-DMMC. According to our knowledge, this is the first multiresidue analytical method by CG–MS enrolling cathinones, amphetamines, and piperazines. The presence of illicit synthetic cathinones in Douro River estuary is here reported for the first time, along with other amphetamine derivatives. The potential of the method to monitor consumption of the target PAS was demonstrated.

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Separation of Enantiomers Using Gas Chromatography: Application in Forensic Toxicology, Food and Environmental Analysis

Cited by 24 publications

References 151 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Cyclodextrins as Dominant Chiral Selective Agents in the Capillary Separation Techniques

Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters

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