Separation of phenylalanine and methionine enantiomers by HPLC method: a comparison of stationary phase types
Authors:
Katarína Hroboňová; Anna Lomenova; Jozef Čižmárik; Jozef Lehotay
Published in:
Čes. slov. Farm., 2017; 66, 62-66
Category:
Original Articles
Overview
The paper deals with enantioselective separation of amino acids by the high performance liquid chromatography method. Separations of enantiomeric forms were tested on the chiral stationary phases based on β-cyclodextrine, isopropyl carbamate cyclofructan 6, and the macrocyclic antibiotic teicoplanin. The best enantioseparation was obtained on the teicoplanin-based chiral stationary phase in the reversed-phase mode. UV spectrophotometric detection at 210 nm was used for detection of amino acids. The method was validated with respect to linearity, precision, limit of detection, limit of quantitation, and recovery. Limits of quantitation for phenylalanine and methionine enantiomers were 0.3 and 0.2 µg.ml–1, respectively. The HPLC method with teicoplanin-based chiral stationary phase was applied for analysis of dietary supplements.
Key words:
separation of enantiomers • HPLC • phenylalanine • methionine
Sources
1. Guo M., Shi T., Duan Y., Zhu J., Li J., Cao Y. Investigation of amino acids in wolfberry fruit (Lycium barbarum) by solid-phase extraction and liquid chromatography with precolumn derivatization. J. Food. Compos. Anal. 2015; 42, 84–90.
2. Zahradníčková H., Haratvich P., Holoubek, I. Historie a význam chirálných analýz aminokyselin v biologických matricích a v životním prostředí. Chem. Listy. 2005; 99, 703–710.
3. Brückner H., Westhauser T. Chromatographic determination of L- and D-amino acids in plants. Amino acids 2003; 24, 43–55.
4. Shinitzky M., Nudelman F., Barda Y., Haimovitz R., Chen E., Dealer D. W. Unexpected differences between D- and L- thyrosine lead to chiral enhancement in racemic mixtures dedicated to the memory of Prof. Shneior Lifson – A great liberal thinker. Orig. Life Evol. Biosphere 2002; 32, 285–297.
5. MacDermott A. J. Electroweak enantioselection and the origin of life. Orig. Life Evol. Biosphere 25 (1995) 191–199.
6. Wu G. Amino Acids: Biochemistry and nutrition. Boca Raton: CRC Press 2013.
7. Armstrong D. W., Youbang L., Ekborgott K. A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations. Chirality 1995; 7, 474–497.
8. Ilisz I., Berkecz R., Forro E., Fülöp F., Armstrong D.W., Peter A. The role of π-acidic and π-basic chiral stationary phases in the high performance liquid chromatographic enantioseparation of unusual β-amino acids. Chirality 2009; 21, 339–348.
9. Sun P., Armstrong D. W. Effective enantiomeric separations of racemic primary amines by the isopropyl carbamate – cyclofructan 6 chiral stationary phase. J. Chromatogr. A 2010; 1217, 4904–4918.
10. Moravčík J., Hroboňová K. Separácia enantiomérov aminokyselín metódou vysokoúčinnej kvapalinovej chromatografie. Čes. slov. Farm. 2014; 63, 4–12.
11. Armstrong D. W., Tang Y., Chen S., Zhou Y., Bagwill C., Chen J.-R. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal. Chem. 1994; 66, 1473–1484.
12. Berthold A., Chen X., Kullman J. P., Armstrong D. W., Gasparrini F., D’Acquarica I., Villani C., Carotti A. Role of the carbohydrate moieties in chiral recognition on teicoplanin-based LC stationary phases. Anal. Chem. 2000; 72, 1767–1780.
13. Lee S. H., Berthod A., Armstrong D. W. Systematic study on the resolution of derivatized amino acids enantiomers on defferent cyclodextrin-bonded stationarz phases. J. Chromatogr. 1992; 603, 83–94.
Labels
Pharmacy Clinical pharmacologyArticle was published in
Czech and Slovak Pharmacy
2017 Issue 2
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