Influence of amino acid moiety accessibility on the chiral recognition of cyclodextrin–amino acid mixed selectors in enantioselective gas chromatography

Stephany, O.; Tisse, Séverine; Coadou, Gaël; Bouillon, Jean‐Philippe; Peulon-Agasse, Valérie; Cardinaël, Pascal

doi:10.1016/j.chroma.2012.10.029

Cited by 17 publications

(5 citation statements)

References 30 publications

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“…Several other approaches to improve enantioselectivity and chromatographic results have been attempted: a) applying two or more chiral selectors in a single column, for example 1) mixing two CDs [53][54][55][56] although the synergy in terms of enantioselectivity was not as high as expected; similar unsatisfactory results were obtained when two CD units were condensed; and 2) mixing two structurally different chiral selectors, e.g. amino acid derivatives and cyclodextrin derivatives; these were grafted simultaneously [57], linked to polysiloxane [58] or covalently linked to amino acid derivatives/cyclodextrins [59,60]. These binary phases retained the enantioselective properties of each component, thus extending the range of enantioseparation achievable.…”

Section: Chemistry Of Cyclodextrin Derivatives For Es-gcmentioning

confidence: 99%

Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis

Cagliero

Sgorbini

Cordero

et al. 2017

Springer Handbook of Odor

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This chapter concerns enantioselective gas chromatography with cyclodextrin derivatives as chiral stationary phases for chiral recognition of volatile odorants in the flavour and fragrance field. The text is divided into two main parts. The first one is more general and deals with enantiomers and odour and need for chiral recognition, evolution of chiral stationary phases for enantioselective GC since its beginning, followed by the history of cyclodextrins and their applications to enantioselective GC. It also includes some theoretical aspects of enantiomer separation with cyclodextrin derivatives and their influence on routine chiral recognition.The second part concerns the strategy of chiral recognition in routine analysis with cyclodextrin derivatives as chiral stationary phases illustrated by examples with real natural product samples. This part describes enantiomer automatic identification or their excess or ratio determination in complex mixtures by enantioselective GC combined with mass spectrometry; in particular it deals with the potential of multidimensional techniques and of fast GC in chiral recognition and the role played by mass spectrometry. The last paragraph concerns the use of total analysis systems in chiral recognition.

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Section: Chemistry Of Cyclodextrin Derivatives For Es-gcmentioning

confidence: 99%

Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis

Cagliero

Sgorbini

Cordero

et al. 2017

Springer Handbook of Odor

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“…k MIP S−CIT k NIP S−CIT (7) where k was the partition coefficient for each polymer [37] and the imprinting factor (k MIP /k NIP ) for the longest retained Electrochromatographic separation of R,S-CIT forms by NIP S-CIT monolithic column. Conditions; buffer: 50%, 10.0 mM PB pH 7.0; 50% ACN; marker THA concentration: 0.5 mg/mL; sample S-citalopram concentration: 100 ppm; sample injection: 5 kV, 3 s; UV wavelength: 220 nm; applied electrical field: 10 kV; applied pressure: 0 mbar.…”

Section: If =mentioning

confidence: 99%

S‐citalopram imprinted monolithic columns for capillary electrochromatography enantioseparations

et al. 2021

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In this study, the molecular imprinting method was used to separate enantiomeric forms of chiral antidepressant drug, R,S-citalopram (R,S-CIT) in aqueous solution by CEC system combining the advantages of capillary electrophoresis (CE) and high-performance liquid chromatography (HPLC). For that, an amino acid-based molecularly imprinted monolithic capillary column was designed and used as a stationary phase for selective separation of S-citalopram (S-CIT) for the first time. S-CIT was selectively separated from the aqueous solution containing the other enantiomeric form of R-CIT, which is the same in size and shape as the template molecule. Morphology of the molecularly imprinted (MIP S-CIT) and non-imprinted (NIP S-CIT) monolithic capillary columns was observed by scanning electron microscopy. Imprinting efficiency of MIP S-CIT monolithic capillary column used for selective S-CIT separation was verified by comparing with NIP S-CIT and calculated imprinting factor (I.F:1.81) proved the high selectivity of the MIP S-CIT for S-CIT. Cavities formed for S-CIT form enabled selective (α = 2.08) separation of the target molecule from the other enantiomeric R-CIT form. Separation was achieved in a short period of 10 min, with the electrophoretic mobility of 7.68 × 10 −6 m 2 /Vs for R,S-CIT at pH 7.0 10 mM PB and 50% ACN ratio. The performance of both MIP S-CIT and NIP S-CIT columns was estimated by repeating the R,S-CIT separations with intra-batch and inter-batch studies for reproducibility of retention times of R,S-CITs. Estimated RSD values that are lower than 2% suggest that the monolithic columns separate R,S-CIT enantiomers without losing separation efficiency.

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“…8,9 Inclusion complex formation and chiral separation of amino acids and amino acid derivatives by CDs have been studied with different experimental techniques such as electrospray mass spectrometry, capillary electrophoresis and gas chromatography. [10][11][12][13][14] They have also been theoretically studied by molecular mechanics 15 and dynamics. 13,16,17 In these theoretical studies the presence of organic modifiers is represented by different values of the dielectric constant in the electrostatic contribution to the interaction energy.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of the separation of valine enantiomers by β-cyclodextrin with different solvents: a molecular mechanics and dynamics simulation

Alvira

2015

Tetrahedron: Asymmetry

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Influence of amino acid moiety accessibility on the chiral recognition of cyclodextrin–amino acid mixed selectors in enantioselective gas chromatography

Cited by 17 publications

References 30 publications

Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis

Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis

S‐citalopram imprinted monolithic columns for capillary electrochromatography enantioseparations

Theoretical study of the separation of valine enantiomers by β-cyclodextrin with different solvents: a molecular mechanics and dynamics simulation

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