Gas chromatographic separation of enantiomers on novel chiral stationary phases

Xie, Sheng‐Ming; Chen, Xue‐Xian; Zhang, Junhui; Yuan, Li‐Ming

doi:10.1016/j.trac.2020.115808

Cited by 84 publications

(28 citation statements)

References 80 publications

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“…Five chiral ligands were selected, and five chiral MOFs were synthesized by grafting different ligands on MIL-101-NH2. They are mainly recognized by hydrogen bonds and π-π interactions, so they combine the advantages of large specific surface area and strong adsorption affinity of MOFs [ 62 ].…”

Section: Chromatographic Separationmentioning

confidence: 99%

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

et al. 2021

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With the rapid development of global industry and increasingly frequent product circulation, the separation and detection of chiral drugs/pesticides are becoming increasingly important. The chiral nature of substances can result in harm to the human body, and the selective endocrine-disrupting effect of drug enantiomers is caused by differential enantiospecific binding to receptors. This review is devoted to the specific recognition and resolution of chiral molecules by chromatography and membrane-based enantioseparation techniques. Chromatographic enantiomer separations with chiral stationary phase (CSP)-based columns and membrane-based enantiomer filtration are detailed. In addition, the unique properties of these chiral resolution methods have been summarized for practical applications in the chemistry, environment, biology, medicine, and food industries. We further discussed the recognition mechanism in analytical enantioseparations and analyzed recent developments and future prospects of chromatographic and membrane-based enantioseparations.

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Section: Chromatographic Separationmentioning

confidence: 99%

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

et al. 2021

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“…For many years, chiral separations have been realized by many chromatographic methods including liquid, supercritical fluid chromatography, and GC as well as CE [4–8]. A glimpse at the literature in the last few decades reveals the fact that a plethora of literature emerged focusing on the direct chiral separation techniques where no chemical derivatization is required [9–16].…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoresis and molecular modeling of the chiral separation of aromatic amino acids using α/β‐cyclodextrin and 18‐crown‐6

et al. 2021

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In this work, chiral separation of enantiomers of three amino acids was achieved using capillary electrophoresis technique with α‐cyclodextrin (αCD) as a running buffer additive. Only tryptophan has exhibited baseline separation in the presence of αCD, while the enantiomers of the other two amino acids, phenylalanine and tyrosine, were only partially separated. The addition of 18‐crown‐6 (18C6) as a second additive imparted only slight improvement to the separation of all enantiomers. On the other hand, all three racemic amino acid mixtures demonstrated no indication of separation when the larger cavity cyclodextrin members, β‐ and γCD, are used as running buffer chiral additives. However, remarkable improvements in the separation of the enantiomers of phenylalanine and tyrosine were obtained when 18C6 is used together with βCD as a running buffer additive. Surprisingly, tryptophan enantiomers were not separated by the dual additive system of cyclodextrin and crown ether. Using electrospray ionization mass spectrometry (ESI‐MS), all amino acids were found to form stable binary complexes with individual hosts as well as ternary compounds involving the crown ether and the cyclodextrin. Furthermore, we used molecular dynamics (MD) simulations to build a clear picture about the interaction between the guest and the hosts. Most of these complexes remained stable throughout the simulation times, and the molecular dynamics study allowed better understanding of these supramolecular assemblies.

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“…Many technologies and methods have been developed for enantioselective analysis, including HPLC [11][12][13][14], CE [15][16][17][18], GC [19,20], supercritical fluid chromatography [21], and nuclear magnetic resonance (NMR) [22,23]. These methods have been widely applied and intensively investigated and developed over the past several decades.…”

Section: Introductionmentioning

confidence: 99%

Direct distinction of ibuprofen and flurbiprofen enantiomers by ion mobility mass spectrometry of their ternary complexes with metal cations and cyclodextrins in the gas phase

Yang

et al. 2021

J of Separation Science

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Enantiomeric drugs are widely used and play important roles in pharmaceuticals. Ion mobility spectrometry coupled with mass spectrometry technology provides a unique method for distinguishing the enantiomeric drugs, enantiomeric identification, and quantitation in the gas phase. In this study, enantiomeric molecules of ibuprofen and flurbiprofen were clearly recognized by forming host-guest complex ions using trapped ion mobility time-of-flight mass spectrometry. Ternary complex ions can be produced easily by electrospray ionization of the mixed solutions of ibuprofen, cyclodextrins, and CaCl 2 , LiCl, or NaCl, as well as flurbiprofen, cyclodextrins, and CaCl 2 . The relative contents of different chiral ibuprofens in a mixed solution were also quantitatively measured. This new method is a simple, effective, and a convenient enantioselective analysis method.

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Gas chromatographic separation of enantiomers on novel chiral stationary phases

Cited by 84 publications

References 80 publications

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

Capillary electrophoresis and molecular modeling of the chiral separation of aromatic amino acids using α/β‐cyclodextrin and 18‐crown‐6

Direct distinction of ibuprofen and flurbiprofen enantiomers by ion mobility mass spectrometry of their ternary complexes with metal cations and cyclodextrins in the gas phase

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