Ultra-trace Analysis of Enantiomeric Impurities in Proteinogenic N-Fmoc-Amino-acid Samples on Cinchona Alkaloid-based Chiral Stationary Phases

A. Péter, Nóra Grecsó, G. Tóth, F. Fülöp, Wolfgang Lindner, I. Ilisz

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The enantiomeric purity of Nα-Fmoc-protected amino acids is crucial from the viewpoint of peptide synthesis; therefore, a sensitive high-performance liquid chromatographic protocol was developed for the identification and quantification of enantiomeric impurities of commercially available Nα-Fmoc-protected amino acids on Cinchona alkaloid quinine- and quinidine-based weak anion exchanger-type chiral stationary phases. In the course of the evaluation of the chiral chromatographic method, the effect of the mobile phase composition, nature, and concentration of different additives were optimized. The specific phenomenon that quinine- and quinidine-based chiral stationary phases behave as pseudo-enantiomers permits that the sequence of elution of the enantiomers might be reversed by simple column switching. This is quite advantageous as regards the separation of the minor component in the presence of the major one. The method developed permits detection of less than 0.01% enantiomeric impurity in the presence of the major enantiomer.

Original languageEnglish
JournalIsrael Journal of Chemistry
DOIs
Publication statusAccepted/In press - 2016

Fingerprint

Cinchona Alkaloids
Trace analysis
Enantiomers
Quinidine
Quinine
Impurities
Amino Acids
Phase composition
Anions
Peptides
Liquids

Keywords

  • Amino acids
  • Chiral resolution
  • Cinchona alkaloid-based chiral stationary phases
  • Enantiomeric impurities

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Ultra-trace Analysis of Enantiomeric Impurities in Proteinogenic N-Fmoc-Amino-acid Samples on Cinchona Alkaloid-based Chiral Stationary Phases",
abstract = "The enantiomeric purity of Nα-Fmoc-protected amino acids is crucial from the viewpoint of peptide synthesis; therefore, a sensitive high-performance liquid chromatographic protocol was developed for the identification and quantification of enantiomeric impurities of commercially available Nα-Fmoc-protected amino acids on Cinchona alkaloid quinine- and quinidine-based weak anion exchanger-type chiral stationary phases. In the course of the evaluation of the chiral chromatographic method, the effect of the mobile phase composition, nature, and concentration of different additives were optimized. The specific phenomenon that quinine- and quinidine-based chiral stationary phases behave as pseudo-enantiomers permits that the sequence of elution of the enantiomers might be reversed by simple column switching. This is quite advantageous as regards the separation of the minor component in the presence of the major one. The method developed permits detection of less than 0.01{\%} enantiomeric impurity in the presence of the major enantiomer.",
keywords = "Amino acids, Chiral resolution, Cinchona alkaloid-based chiral stationary phases, Enantiomeric impurities",
author = "A. P{\'e}ter and N{\'o}ra Grecs{\'o} and G. T{\'o}th and F. F{\"u}l{\"o}p and Wolfgang Lindner and I. Ilisz",
year = "2016",
doi = "10.1002/ijch.201600058",
language = "English",
journal = "Israel Journal of Chemistry",
issn = "0021-2148",
publisher = "Wiley-VCH Verlag",

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AU - Péter, A.

AU - Grecsó, Nóra

AU - Tóth, G.

AU - Fülöp, F.

AU - Lindner, Wolfgang

AU - Ilisz, I.

PY - 2016

Y1 - 2016

N2 - The enantiomeric purity of Nα-Fmoc-protected amino acids is crucial from the viewpoint of peptide synthesis; therefore, a sensitive high-performance liquid chromatographic protocol was developed for the identification and quantification of enantiomeric impurities of commercially available Nα-Fmoc-protected amino acids on Cinchona alkaloid quinine- and quinidine-based weak anion exchanger-type chiral stationary phases. In the course of the evaluation of the chiral chromatographic method, the effect of the mobile phase composition, nature, and concentration of different additives were optimized. The specific phenomenon that quinine- and quinidine-based chiral stationary phases behave as pseudo-enantiomers permits that the sequence of elution of the enantiomers might be reversed by simple column switching. This is quite advantageous as regards the separation of the minor component in the presence of the major one. The method developed permits detection of less than 0.01% enantiomeric impurity in the presence of the major enantiomer.

AB - The enantiomeric purity of Nα-Fmoc-protected amino acids is crucial from the viewpoint of peptide synthesis; therefore, a sensitive high-performance liquid chromatographic protocol was developed for the identification and quantification of enantiomeric impurities of commercially available Nα-Fmoc-protected amino acids on Cinchona alkaloid quinine- and quinidine-based weak anion exchanger-type chiral stationary phases. In the course of the evaluation of the chiral chromatographic method, the effect of the mobile phase composition, nature, and concentration of different additives were optimized. The specific phenomenon that quinine- and quinidine-based chiral stationary phases behave as pseudo-enantiomers permits that the sequence of elution of the enantiomers might be reversed by simple column switching. This is quite advantageous as regards the separation of the minor component in the presence of the major one. The method developed permits detection of less than 0.01% enantiomeric impurity in the presence of the major enantiomer.

KW - Amino acids

KW - Chiral resolution

KW - Cinchona alkaloid-based chiral stationary phases

KW - Enantiomeric impurities

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