HPLC Separation of Enantiomers of α-Substituted Proline Analogues by the Application of (S)-N-(4-Nitrophenoxycarbonyl)phenylalanine Methoxyethyl Ester as Chiral Derivatizing Agent

A. Péter, G. Török, E. Vékes, J. Van Betsbrugge, D. Tourwé

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Indirect high-performance liquid chromatographic enantioresolution of highly constrained α-substituted proline analogues as (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester derivatives is reported. The diastereoisomers formed were analysed under reversed-phase conditions by means of gradient elution. Baseline separation was achieved for all of the derivatives of each investigated analyte. The elution sequence was determined, and this allows identification of the configuration of the a-substituted proline analogues in the peptide epimers, resulting from use of the racemates of proline analogues in peptide synthesis.

Original languageEnglish
Pages (from-to)17-29
Number of pages13
JournalJournal of Liquid Chromatography and Related Technologies
Volume27
Issue number1
DOIs
Publication statusPublished - 2004

Fingerprint

Enantiomers
Proline
High Pressure Liquid Chromatography
Derivatives
Peptides
Liquids
N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester

Keywords

  • α-Substituted proline analogues
  • ((S)-NIFE)
  • (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester
  • Enantiomers
  • HPLC separation
  • Peptides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

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T1 - HPLC Separation of Enantiomers of α-Substituted Proline Analogues by the Application of (S)-N-(4-Nitrophenoxycarbonyl)phenylalanine Methoxyethyl Ester as Chiral Derivatizing Agent

AU - Péter, A.

AU - Török, G.

AU - Vékes, E.

AU - Van Betsbrugge, J.

AU - Tourwé, D.

PY - 2004

Y1 - 2004

N2 - Indirect high-performance liquid chromatographic enantioresolution of highly constrained α-substituted proline analogues as (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester derivatives is reported. The diastereoisomers formed were analysed under reversed-phase conditions by means of gradient elution. Baseline separation was achieved for all of the derivatives of each investigated analyte. The elution sequence was determined, and this allows identification of the configuration of the a-substituted proline analogues in the peptide epimers, resulting from use of the racemates of proline analogues in peptide synthesis.

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KW - α-Substituted proline analogues

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KW - HPLC separation

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