A study of mass transfer kinetics of alanyl-alanine on a chiral crown ether stationary phase

Sharma, Kavita; Park, Se Won

doi:10.1016/j.chroma.2011.06.029

Cited by 9 publications

(6 citation statements)

References 52 publications

(73 reference statements)

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“…In HPLC, it is a reasonable approximation to refer the flow rate to an average pressure in the column rather than to solve the problem of a gradient‐compressed fluid. The associated error in k does not exceed 1% . Note that this sort of correction is not needed if the flow rate is measured at column temperature and pressure.…”

Section: Measurement Of Van't Hoff Plotsmentioning

confidence: 99%

Van't Hoff analysis in chiral chromatography

Аснин

Stepanova

2018

J of Separation Science

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The present review discusses the theory and application of van't Hoff analysis in chiral chromatography, with main focus on liquid chromatography. The topics considered include the physical meaning of van't Hoff equation's parameters, interpretation of thermodynamic data in terms of retention and enantioseparation mechanisms, abnormal behavior of van't Hoff plots, and best practices to avoid biased results.

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Section: Measurement Of Van't Hoff Plotsmentioning

confidence: 99%

Van't Hoff analysis in chiral chromatography

Аснин

Stepanova

2018

J of Separation Science

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“…Asnin et al. used Chirosil RCA [with (+)‐crown ether] for the separations of Ala‐Ala and Gly‐Leu stereoisomers. Both groups used water/methanol solvents acidified with millimolar sulfuric acid.…”

Section: Chiral Separation Of Small Peptidesmentioning

confidence: 99%

“…Conrad et al [28] used a Chirosil SCA with [(-)-crown ether] for the stereoseparation of 12 dipeptides and four tripeptides. Asnin et al [29,123] used Chirosil RCA [with (+)-crown ether] for the separations of Ala-Ala and Gly-Leu stereoisomers. Both groups used water/methanol solvents acidified with millimolar sulfuric acid.…”

Section: Crown Ether Cspsmentioning

confidence: 99%

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Ali

ALOthman

Al–Warthan

et al. 2014

J of Separation Science

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133

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Many chemical and biological processes are controlled by the stereochemistry of small polypeptides (di-, tri-, tetra-, penta-, hexapeptides, etc). The biological importance of peptide stereoisomers is of great value. Therefore, the chiral resolution of peptides is an important issue in biological and medicinal sciences and drug industries. The chiral resolutions of peptide racemates have been discussed with the use of capillary electrophoresis and chromatographic techniques. The various chiral selectors used were polysaccharides, cyclodextrins, Pirkle types, macrocyclic antibiotics, crown ethers, imprinted polymers, etc. The stereochemistry of dipeptides is also discussed. Besides, efforts are made to explain the chiral recognition mechanisms, which will be helpful in understanding existing and developing new stereoselective analyses. Future perspectives of enantiomeric resolution are also predicted. Finally, the review concludes with the demand of enantiomeric resolution of all naturally occurring and synthetic peptides.

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“…Crown ethers, which can form complex with cations selectively, were first introduced by Pedersen in 1967 as cyclic polyethers . Crown ether derivatives based on tetracarboxylic acid and other chiral compounds have been widely used as chiral selectors for the resolution of amino acids, N ‐(3,5‐dinitrobenzoyl)‐α‐amino acids and chiral amines in HPLC. In the previous work, we prepared two novel chiral stationary phases by combining quinine and crown ether moieties, in which quinine provided ion‐exchange site for carboxyl group, crown ether provided complex interaction site for amino group at the same time .…”

Section: Introductionmentioning

confidence: 99%

Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification

Zhao

Wang

et al. 2015

J. Sep. Science

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To improve the chiral recognition capability of a cinchona alkaloid crown ether chiral stationary phase, the crown ether moiety was modified by the chiral group of (1S, 2S)-2-aminocyclohexyl phenylcarbamate. Both quinine and quinidine-based stationary phases were evaluated by chiral acids, chiral primary amines and amino acids. The quinine/quinidine and crown ether provided ion-exchange sites and complex interaction site for carboxyl group and primary amine group in amino acids, respectively, which were necessary for the chiral discrimination of amino acid enantiomers. The introduction of the chiral group greatly improved the chiral recognition for chiral primary amines. The structure of crown ether moiety was proved to play a dominant role in the chiral recognitions for chiral primary amines and amino acids.

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A study of mass transfer kinetics of alanyl-alanine on a chiral crown ether stationary phase

Cited by 9 publications

References 52 publications

Van't Hoff analysis in chiral chromatography

Van't Hoff analysis in chiral chromatography

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification

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