Abstract
The direct and indirect stereochemical resolution of the enantiomers of ring- and α-methyl-substituted phenylalanines and phenylalanine amides was attempted by high-performance liquid chromatographic methods. The direct separation was carried out on two chiral stationary phases, the crown-ether- based Crownpak CR (+), and the teicoplanin-based Chirobiotic T, while the indirect resolution was performed by applying pre-column derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (GITC) and Nα- (2,4-dinitro-5-fluorophenyl)-L-alanine amide (Marfey's reagent, FDAA). The Chirobiotic T column was efficient in the separation of ring- and α-methyl- substituted phenylalanine analogues but was ineffective for the amides of these analogues. The Crownpak CR (+) column separated the ring-substituted phenylalanines and amides, whereas the α-methylated analogues were coeluted. Of the two indirect methods, GITC derivatization seemed more effective than FDAA derivatization. (C) 2000 Elsevier Science B.V.
Recommended Citation
A. Péter et al., "High-performance Liquid Chromatographic Separation of the Enantiomers of Unusual Α-amino Acid Analogues," Journal of Chromatography A, vol. 871, no. 1 thru 2, pp. 105 - 113, Elsevier, Feb 2000.
The definitive version is available at https://doi.org/10.1016/S0021-9673(99)00889-4
Department(s)
Chemistry
Keywords and Phrases
Amino acids; Enantiomer separation
International Standard Serial Number (ISSN)
0021-9673
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2024 Elsevier, All rights reserved.
Publication Date
25 Feb 2000
PubMed ID
10735291
Comments
Hungarian Scientific Research Fund, Grant B-3/96