1. Liquid chromatographic enantioseparation of spin-labelled beta-amino acids
Antal Péter, Roland Török, Karen Wright, Michel Wakselman, Jean Paul Mazaleyrat J Chromatogr A. 2003 Dec 22;1021(1-2):1-10. doi: 10.1016/j.chroma.2003.09.015.
Direct and indirect high-performance liquid chromatographic (HPLC) methods were developed for the enantioseparation of spin-labelled, cyclic, chiral beta-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-beta-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-beta-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 beta-TOAC analogues, the absolute configurations of the enantiomers corresponding to each peak were identified.
2. Direct and indirect high-performance liquid chromatographic enantioseparation of beta-amino acids
Antal Péter, Anita Arki, Erika Vékes, Dirk Tourwé, László Lázár, Ferenc Fülöp, Daniel W Armstrong J Chromatogr A. 2004 Mar 26;1031(1-2):171-8. doi: 10.1016/j.chroma.2003.08.070.
Direct and indirect reversed-phase (RP) high-performance liquid chromatographic methods were developed for the separation of enantiomers of 18 unnatural beta-amino acids, including several beta-3-homo amino acids. The direct separations of the underivatized analytes were performed on chiral stationary phases (CSPs) containing macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T column) and teicoplanin aglycone (Chirobiotic TAG column). The indirect method involved pre-column derivatization with a new chiral derivatizing agent (CDA), (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester ((S)-NIFE), and subsequent separation of diastereomers on Discovery C18 and Hyperpep 300 C18 columns. The different methods were compared in systematic chromatographic examinations. The effects of organic modifier, mobile phase composition, pH and flow rate on the separation were investigated.
3. High-performance liquid chromatographic enantioseparation of beta-amino acids
A Péter, L Lázár, F Fülöp, D W Armstron J Chromatogr A. 2001 Aug 17;926(2):229-38. doi: 10.1016/s0021-9673(01)01078-0.
Direct and indirect high-performance liquid chromatographic methods were developed for the enantioseparation of beta-amino acids (beta-substituted-beta-alanines). Direct separation involved the application of chiral columns: Crownpak CR(+), Chirobiotic T and Chirobiotic R. Indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate or N-alpha-(2,4-dinitro-5-fluorophenyl)-L-alanineamide (Marfey's reagent), with subsequent separation on an achiral column. The chromatographic conditions were varied to achieve optimum separation.
