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Direct high‐performance liquid chromatographic enantioseparation of α‐substituted proline analogues on a quinine‐derived chiral anion‐exchanger stationary phase
Author(s) -
Péter Antal,
Vékes Erika,
Árki Anita,
Tourwé Dirk,
Lindner Wolfgang
Publication year - 2003
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200301524
Subject(s) - chemistry , enantiomer , chromatography , elution , proline , epimer , resolution (logic) , high performance liquid chromatography , ion exchange , organic chemistry , amino acid , ion , computer science , biochemistry , artificial intelligence
Use of a quinine‐derived chiral anion‐exchanger stationary phase for the direct high‐performance liquid chromatographic enantiomer separation of N ‐protected unusual α‐substituted proline analogues is reported. The chromatographic conditions (eluent composition, pH, and buffer concentration) were varied to achieve optimal separation. The readily prepared 2,4‐dinitrophenyl derivatives were well separable, with good efficiency and high resolution. The elution sequences of the enantiomers of the derivatives were determined. Knowledge of the elution sequence allows identification of the configuration of the α‐substituted proline analogues in peptide epimers resulting from use of the racemates in the peptide synthesis. The method also proved suitable for determination of the enantiomeric purity of proline analogues obtained by asymmetric synthesis.