Evaluation of the Enantiomeric Separation of Dipeptides Using a Chiral Crown Ether LC Column

Hilton, M. L.; Armstrong, Daniel W.

doi:10.1080/01483919108049485

Cited by 82 publications

(18 citation statements)

References 14 publications

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“…Since it has been discovered that not only L-amino acids but also D-enantiomers are present in peptides and proteins, chiral analysis of peptides has attracted increasing interest. Several analytical methods have been used for separation of the chiral dipeptides, such as HPLC [4], GC [5], TLC [6], ligand-exchange chromatography [7], CEC [8] and CE [9,10].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of chiral dipeptides by CE‐ESI‐MS employing a partial filling technique with chiral crown ether

Xia

Zhang

et al. 2009

Electrophoresis

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Enantiomer of chiral dipeptides were separated by CE-ESI-MS in a bare fused-silica capillary using (1)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18C 6 H 4 ) as the chiral selector. As 18C 6 H 4 is a kind of nonvolatile chiral selector, in order to prevent from 18C 6 H 4 into the ion-source of CE-ESI-MS, a partial filling technique was employed in this study. Some dipeptides with one chiral center or two chiral centers, such as DL-Leu-DL-Leu, D-Ala-D-Ala and L-Ala-L-Ala, Gly-D-Phe and Gly-L-Phe were used to evaluate this CE-ESI-MS system. Optimized conditions were achivevd with 2.0 mol/L acetic acid (pH 2.15) as the running electrolyte, 5 mM 18C 6 H 4 in 3.0 mol/L acetic acid (pH 2.00) was injected hydrodynamically (50 mbar for 960 s) before sample injection. In total 7.5 mM acetic acid in 80% v/v methanol-water was used as the sheath liquid, and 20 kV applied voltage was used. Under the optimum conditions, these dipeptides were separated and detected. LODs (defined as S/N 5 3) of this method were 0.20, 0.10, 0.05 and 0.10 mmol/L for D-Ala-D-Ala, L-Ala-L-Ala, DL-Leu-DL-Leu, Gly-L-Phe and Gly-D-Phe, respectively. The RSDs (n 5 7) of the method were 0.68-2.08% for migration times and 2.32-5.24% for peak areas. The proposed method was also successfully applied to the enantioselective analysis of these dipeptides in the spiked serum samples with satisfactory results.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of chiral dipeptides by CE‐ESI‐MS employing a partial filling technique with chiral crown ether

Xia

Zhang

et al. 2009

Electrophoresis

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“…6 A number of underivatized stereoisomeric dipeptides were separated by HPLC on a chiral teicoplanin column 7 and use of a chiral Crown ether enabled the resolution of stereoisomers of underivatized synthetic dipeptides. 8 Notably, N-derivatized stereoisomeric tri-and tetra-alanines were resolved using a 2D liquid chromatographic approach combining an achiral reversed and cinchonaalkaloid-based chiral stationary phases. 9 Various approaches for the resolution of stereoisomers of free or derivatized di-and tri-peptides employing capillary electrophoresis together with chiral crown ethers or functionalized cyclodextrins as chiral selectors or the addition of chiral additives such as b-cyclodextrins have also been described.…”

mentioning

confidence: 99%

Gas‐chromatographic separation of stereoisomers of dipeptides

Pätzold¹,

Theis²,

Brückner³

2006

Chirality

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Synthetic dipeptides comprising mixtures of enantiomers, diastereomers, or sequential isomers were converted into their N-perfluoroacetyl dipeptide esters (perfluoroacetyl: trifluoroacetyl, pentafluoroacetyl, heptafluorobutyryl; ester: methyl, 1-propyl, 2-propyl, 2,2,2-trifluoroethyl) and analyzed by GC-MS on the chiral stationary phases Chirasil-L-Val and Lipodex-E using helium as carrier gas. Further, dipeptides were converted into their N-trifluoroacetyl dipeptide S-(+)-2-butyl esters and separated on achiral phenylmethyl polysiloxane column (HP-5 MS). Derivatization of dipeptides was performed at ambient temperature in order to avoid formation of the corresponding diketopiperazines. The best separation of stereoisomers was achieved with TFA and PFP methyl esters on Chirasil-L-Val.

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“…A ciklofruktánokat, mint királis szelektorokat, először Cram és munkatársai kezdték el fejleszteni [31,32]. Az első, úgynevezett királis koronaéter állófázisokat az 1990-es években hozták kereskedelmi forgalomba [33][34][35][36]. A ciklofruktán általánosságban 6 vagy több, egymáshoz -(1→2) helyzetben kapcsolódó D-fruktofuranóz alegységből épül fel.…”

Section: A Ciklofruktán Alapú áLlófázisokunclassified

“…Több megjelent közlemény igazolja, hogy ha nincs sztérikus illeszkedés, nem megfelelő az elválasztás sem [33,[54][55][56]. Továbbá a primer amino-csoport és a királis centrum közötti távolság is fontos szerepet tölt be a királis megkülönböztetés szempontjából.…”

Section: A Kémiai Szerkezet éS Kromatográfiás Viselkedés öSszefüggéseunclassified

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Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására

Aranyi¹

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Evaluation of the Enantiomeric Separation of Dipeptides Using a Chiral Crown Ether LC Column

Cited by 82 publications

References 14 publications

Enantiomeric separation of chiral dipeptides by CE‐ESI‐MS employing a partial filling technique with chiral crown ether

Enantiomeric separation of chiral dipeptides by CE‐ESI‐MS employing a partial filling technique with chiral crown ether

Gas‐chromatographic separation of stereoisomers of dipeptides

Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására

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