The stereoselective separation of serine containing peptides by zwitterionic ion exchanger type chiral stationary phases and the study of serine racemization mechanisms by isotope exchange and tandem mass spectrometry

Reischl, Roland; Lindner, Wolfgang

doi:10.1016/j.jpba.2015.02.014

Cited by 9 publications

(6 citation statements)

References 43 publications

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“…High-performance LC (HPLC) separation of peptide enantiomer and diastereomer separations without derivatization have been reported, for example on macrocyclic antibiotics chiral stationary phases (CSPs), [13][14][15][16][17] , chiral crown ether CSPs, 18 chiral ligand-exchange CSPs, 19 and zwitterionic cinchona alkaloid based CSPs. [20][21][22][23] The aim of this work was to determine and propose generic screening conditions as well as an initial simple separation strategy allowing the rapid separation of peptide enantiomers in polar organic (PO) elution mode with ionic additives which would be equally useful for peptide epimer and diastereomer separations on chiral zwitterionic stationary phase derived from quinine and quinidine (Chiralpak ZWIX(+) and ZWIX(-)). [24][25][26] In all the tested mobile phase conditions, a fixed concentration of a basic and an acidic additive was maintained, in order to control the ionic state of both analyte and chiral selector.…”

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confidence: 99%

“…Besides strategies involving chiral derivatizing agents such as o‐phthaldialdehyde/chiral thiol and Marfey's reagent, a few enantio‐ and stereoselective methods for underivatized peptides implementing separation on chiral stationary phases or by capillary electrophoresis with chiral additives have been proposed. High‐performance LC (HPLC) separation of peptide enantiomer and diastereomer separations without derivatization have been reported, for example on macrocyclic antibiotics chiral stationary phases (CSPs),, chiral crown ether CSPs, chiral ligand‐exchange CSPs, and zwitterionic cinchona alkaloid based CSPs …”

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confidence: 99%

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Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

et al. 2015

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Peptide stereoisomer analysis is of importance for quality control of therapeutic peptides, the analysis of stereochemical integrity of bioactive peptides in food, and the elucidation of the stereochemistry of peptides from a natural chiral pool which often contains one or more D-amino acid residues. In this work, a series of model peptide stereoisomers (enantiomers and diastereomers) were analyzed on a zwitterionic ion-exchanger chiral stationary phase (Chiralpak ZWIX(+) 5 µm), in order to investigate the retention and separation performance for such compounds on this chiral stationary phase and elucidate its utility for this purpose. The goal of the study focused on 1) investigations of the effects of the sample matrix used to dissolve the peptide samples; 2) optimization of the mobile phase (enabling deriving information on factors of relevance for retention and separation); and 3) derivation of structure-selectivity relationships. It turned out that small di- and tripeptides can be well resolved under optimized conditions, typically with resolutions larger than 1.5. The optimized mobile phase often consisted of methanol-tetrahydrofuran-water (49:49:2; v/v/v) with 25 mM formic acid and 12.5 mM diethylamine. This work proposes some guidance on which mobile phases can be most efficiently used for peptide stereoisomer separations on Chiralpak ZWIX. Chirality 28:5-16, 2016. © 2015 Wiley Periodicals, Inc.

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Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

et al. 2015

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“…Specifically, the heart-cut 2D- for the enantio-and diastereoseparation of underivatized homo and heterochiral di-, tri-and tetrapeptides applying PI mode [82,[112][113][114]. ZWIX(+) and ZWIX(-) were applied for the chiral discrimination of di-and tripeptides Leu-Val and Gly-Gly-Val [85], di-, tri-, and tetrapeptides containing Ser and Thr [115] as well as homo-and heterochiral peptides of Gly-Asn, Gly-Asp, Gly-Leu, Gly-Ser, Ala-Val, Pro-Phe, Leu-Leu, Leu-Leu-Leu, etc. [116].…”

Section: Separation Of N-derivatized Amino Acids In Biological Matricmentioning

confidence: 99%

Liquid chromatographic enantiomer separations applying chiral ion-exchangers based on Cinchona alkaloids

Ilisz

Bajtai

Lindner

et al. 2018

Journal of Pharmaceutical and Biomedical Analysis

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“…Concerning the enantiomer separations, the stereoselective separations of the serine-containing peptides by the zwitterionic type CSPs (Chiralpak ZWIX columns) have been reported [43].…”

Section: Reversed-phase Separation and Enantiomer Separation Of Ser-gmentioning

confidence: 99%

Multi-Dimensional HPLC Analysis of Serine Containing Chiral Dipeptides in Japanese Traditional Amber Rice Vinegar

et al. 2018

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Several D-amino acids have been identified in higher animals including humans, and are now increasingly recognized as biologically active substances and/or biomarkers. Therefore, the presence of related compounds, such as dipeptides, containing D-amino acids in biological matrices is one of the recent topics of increasing interest. In the present study, on-line multi-dimensional HPLC systems combining a narrowbore reversed-phase column (KSAARP, 1.5 mm i.d. x 500 mm), a weak anion-exchange column (KSAAAX, 1.5 mm i.d. x 250 mm) and a Pirkle-type enantioselective column (KSAACSP-001S or R, 1.5 mm i.d. x 250 mm) have been designed for the chiral analysis of Ser-containing dipeptides in fermented products. As target analytes, Ser-Gly and Gly-Ser were selected. For the sensitive analysis, the dipeptides were pre-column derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) to form the NBD-dipeptides, which were detected upon their fluorescence. During the selective multi-dimensional analysis, the target dipeptides were separated from other substances by the reversed-phase and anion-exchange columns as their D/L scalemic mixtures and automatically introduced to the enantioselective column, where the D,L-forms were separated with selectivity / separation factor (α) and resolution (Rs) values higher than 1.07 and 0.71, respectively. The present 3D-HPLC system was well applicable to the analysis of Japanese traditional amber rice vinegar where relatively large amounts of the L-dipeptides and trace amount of D-Ser-Gly were observed.

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The stereoselective separation of serine containing peptides by zwitterionic ion exchanger type chiral stationary phases and the study of serine racemization mechanisms by isotope exchange and tandem mass spectrometry

Cited by 9 publications

References 43 publications

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

Liquid chromatographic enantiomer separations applying chiral ion-exchangers based on Cinchona alkaloids

Multi-Dimensional HPLC Analysis of Serine Containing Chiral Dipeptides in Japanese Traditional Amber Rice Vinegar

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