JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2017, 66(2):62-66 | DOI: 10.36290/csf.2017.008

Separation of phenylalanine and methionine enantiomers by HPLC method: a comparison of stationary phase types

Katarína Hroboňová1,*, Anna Lomenova1, Jozef Čižmárik2, Jozef Lehotay3
1 Ústav analytickej chémie, Fakulta chemickej a potravinárskej technológie, Slovenská technická univerzita v Bratislave, Slovenská republika
2 Katedra farmaceutickej chémie, Farmaceutická fakulta, Univerzita Komenského, Slovenská republika
3 Katedra chémie, Fakulta prírodných vied, Univerzita Sv. Cyrila a Metoda v Trnave, Slovenská republika

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.

Keywords: separation of enantiomers; HPLC; phenylalanine; methionine
Grants and funding:

Práca vznikla za podpory grantu APVV-15-0355 Agentúry na podporu výskumu a vývoja Autori ďakujú prof. D.W. Armstrongovi za poskytnutie chirálnych stacionárnych fáz Chirobiotic T a IP-CF6.

Received: March 14, 2017; Accepted: April 11, 2017; Published: February 1, 2017  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Hroboňová K, Lomenova A, Čižmárik J, Lehotay J. Separation of phenylalanine and methionine enantiomers by HPLC method: a comparison of stationary phase types. Čes. slov. farm. 2017;66(2):62-66. doi: 10.36290/csf.2017.008.
Download citation

References

  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. Go to original source...
  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. Go to original source... Go to PubMed...
  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. Go to original source... Go to PubMed...
  5. MacDermott A. J. Electroweak enantioselection and the origin of life. Orig. Life Evol. Biosphere 25 (1995) 191-199. Go to original source... Go to PubMed...
  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. Go to original source...
  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. Go to original source... Go to PubMed...
  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. Go to original source... Go to PubMed...
  10. Moravčík J., Hroboňová K. Separácia enantiomérov aminokyselín metódou vysokoúčinnej kvapalinovej chromatografie. Čes. slov. Farm. 2014; 63, 4-12. Go to original source...
  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. Go to original source...
  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. Go to original source... Go to PubMed...
  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. Go to original source...




Czech and Slovak Pharmacy

Madam, Sir,
please be aware that the website on which you intend to enter, not the general public because it contains technical information about medicines, including advertisements relating to medicinal products. This information and communication professionals are solely under §2 of the Act n.40/1995 Coll. Is active persons authorized to prescribe or supply (hereinafter expert).
Take note that if you are not an expert, you run the risk of danger to their health or the health of other persons, if you the obtained information improperly understood or interpreted, and especially advertising which may be part of this site, or whether you used it for self-diagnosis or medical treatment, whether in relation to each other in person or in relation to others.

I declare:

  1. that I have met the above instruction
  2. I'm an expert within the meaning of the Act n.40/1995 Coll. the regulation of advertising, as amended, and I am aware of the risks that would be a person other than the expert input to these sites exhibited


No

Yes

If your statement is not true, please be aware
that brings the risk of danger to their health or the health of others.