Liquid chromatographic enantioseparation of spin-labelled β-amino acids

Antal Péter, Roland Török, Karen Wright, Michel Wakselman, Jean Paul Mazaleyrat

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Direct and indirect high-performance liquid chromatographic (HPLC) methods were developed for the enantioseparation of spin-labelled, cyclic, chiral β-amino acids containing nitroxide free radicals, trans-3-amino-1-oxyl-2,2, 5,5-tetramethylpyrrolidine-4-carboxylic acid (trans-POAC), cis-4-amino-1-oxyl-2, 2,6,6-tetramethylpiperidine-3-carboxylic acid (cis-β-TOAC) and their N-Fmoc-protected analogues, synthesized in racemic and enantiomerically pure forms. The direct method involved the use of a Chiralcel OD-RH column, while indirect separation was carried out by application of either 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or (S)-N-(4-nitrophenoxycarbonyl)-phenylalanine methoxyethyl ester as chiral derivatizing agent. Use of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) as chiral derivatizing agent failed because of the low of yield of the derivatization reaction. Selection and variation of the mobile phase was restricted by the sensitivity of the spin-labelled amino acids to acidic conditions. Conditions affording the best resolution were found and the differences in separation capability of the methods were noted. The sequence of elution of the enantiomers was determined by different methods and, in the case of the β-TOAC analogues, the absolute configurations of the enantiomers corresponding to each peak were identified.

Original languageEnglish
Pages (from-to)1-10
Number of pages10
JournalJournal of Chromatography A
Volume1021
Issue number1-2
DOIs
Publication statusPublished - Dec 22 2003

Keywords

  • (S)-N-(4-Nitrophenoxycarbonyl)-phenylalanine methoxyethyl ester
  • 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl isothiocyanate
  • Amino acids
  • CC
  • Derivatization
  • Enantiomer separation
  • Spin-labelled β-amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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