Chromatographic methods for monitoring the optical isomers of unusual aromatic amino acids

Journal of Chromatography A

Volumn 797, Issue 1-2, 1998, Pages 165-176

  Péter, Antal ^a   Török, Gabriella ^a   Tóth, Géza ^b   Van Den Nest, Wim ^c   Georges Laus, ^c   Tourwé, Dirk ^c  

^a UNIVERSITY OF SZEGED   (Hungary)

^b INSTITUTE OF BIOCHEMISTRY   (Hungary)

^c VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Amino acids; Enantiomer separation

Indexed keywords

ALANINE DERIVATIVE; AROMATIC AMINO ACID; CARBOLINE DERIVATIVE; GLUCOPYRANOSIDE; ISOTHIOCYANIC ACID DERIVATIVE; PHENYLALANINE; TETRAHYDROISOQUINOLINE; TETRALIN DERIVATIVE; TRYPTOPHAN; TYROSINE;

CHIRALITY; CONFERENCE PAPER; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0032570994     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9673(97)00967-9     Document Type: Conference Paper

References (45)

1. Kazmierski W., Hruby W.J. Tetrahedron. 44:1988;697.
2. Hruby V.J., Al-Obeidi F., Kazmierski W. Biochem. J. 44:1990;697.
3. A. Péter, G. Tóth, Anal. Chim. Acta (in press).
4. Hruby V.J., Gehrig C.A. Med. Res. Rev. 9:1989;343.
5. Schiller P.W., Thi Nguen M.D., Weltrowska G., Wilkes B.C., Marsden B.J., Lemieux C., Chung N.N. Proc. Natl. Acad. Sci. USA. 89:1992;11871.
6. Tóth G., Darula Zs., Péter A., Fülöp F., Tourwé D., Jaspers H., Verheyden P., Böcskei Zs., Tóth Z., Borsodi A. J. Med. Chem. 40:1997;990.
7. W.H. Pirkle, J. Finn, in: J. Morrison (Ed.), Asymmetric Synthesis, Vol. I, Analytical Methods, Academic Press, New York, 1983, Ch. 6.
8. W.F. Lindner, C. Petterson, in: I. Wainer (Ed.), Liquid Chromatography in Pharmaceutical Development: An Introduction, Part 1, Aster, Springfield, VA, 1985. p. 63.
9. Armstrong D.W., Han S.M. CRC Crit. Rev. Anal. Chem. 19:1988;175.
10. Davankov V.A., Kurganov A.A., Bochkov A.S. Adv. Chromatogr. 22:1983;71.
11. Petterson C. Trends Anal. Chem. 7:1988;209.
12. W.F. Lindner, in: L. Crane, B. Zief (Eds.), Chromatographic Chiral Separations, Marcel Dekker, New York, 1987, p. 91.
13. W.F. Lindner, in: J.F. Lawrence, R.W. Frei (Eds.), Chemical Derivatization in Analytical Chemistry, Vol. 2, Plenum, New York, 1982, p. 145.
14. T. Nambara, in: W.S. Hancock (Ed.), CRC Handbook of HPLC for the Separation of Amino Acids, Peptides and Proteins, Vol. I, CRC Press, Boca Raton, FL, 1984, p. 383.
15. Nimura N., Ogura H., Kinoshita T. J. Chromatogr. 202:1980;375.
16. Kinoshita T., Kasahara Y., Nimura N. J. Chromatogr. 210:1981;77.
17. Nimura N., Toyama A., Kinoshita T. J. Chromatogr. 316:1984;547.
18. Marfey P. Carlsberg Res. Commun. 49:1984;591.
19. Szókán Gy., Mezõ G., Hudecz F. J. Chromatogr. 444:1988;115.
20. Einarsson S., Joseffson B., Möller P., Sanchez D. Anal. Chem. 59:1987;1191.
21. S. Einarsson, G. Hansson, in: C.T. Mant, R.S. Hodges (Eds.), High-performance Liquid Chromatography of Peptides and Proteins, CRC Press, Boca Raton, FL, 1991, p. 369.
22. Görög S., Gazdag M. J. Chromatogr. B. 695:1994;51.
23. C.W. Gehrke, F.E. Kaiser, K.C.T. Kuo, R.W. Zumwalt, in: R.W. Zumwalt, K.C.T. Kuo, C.W. Gehrke (Eds.), Amino Acid Analysis by Gas Chromatography, Vol. I, CRC Press, Boca Raton, FL, 1987, Ch. 2.
24. E. Bayer, G. Nicholson, H. Frank, in: R.W. Zumwalt, K.C.T. Kuo, C.W. Gehrke (Eds.), Amino Acid Analysis by Gas Chromatography, Vol. II, CRC Press, Boca Raton, FL, 1987, Ch. 2.
25. H. Frank, in: R.W. Zumwalt, K.C.T. Kuo, C.W. Gehrke (Eds.), Amino Acid Analysis by Gas Chromatography, Vol. II, CRC Press, Boca Raton, FL, 1987, Ch. 3.
26. I. Abe, S. Kuramato, in: R.W. Zumwalt, K.C.T. Kuo, C.W. Gehrke (Eds.), Amino Acid Analysis by Gas Chromatography, Vol. III, CRC Press, Boca Raton, FL, 1987, Ch. 2.
27. IUPAC-IUB JCBN recommendations, J. Biol. Chem. 264 (1989) 668.
28. Péter A., Tóth G., Cserpán E., Tourwé D. J. Chromatogr. A. 660:1994;283.
29. Péter A., Tóth G., Tourwé D. J. Chromatogr. A. 668:1994;331.
30. Péter A., Tóth G., Olajos E., Fülöp F., Tourwé D. J. Chromatogr. A. 705:1995;257.
31. Péter A., Tóth G., Török G., Tourwé D. J. Chromatogr. A. 728:1996;455.
32. Majer P., Slaninova J., Lebl M. Int. J. Peptide Protein Res. 43:1994;62.
33. Porter J., Dykert J., Rivier J. Int. J. Peptide Protein Res. 30:1987;13.
34. J. Van Betsbrugge, Ph.D. Thesis, Vrije Universiteit Brussel, Belgium, 1997.
35. Pictet A., Spengler T. Chem. Ber. 44:1911;2030.
36. Lebl M., Tóth G., Slaninova J., Hruby V.J. Int. J. Pept. Protein Res. 40:1992;148.
37. Verschueren K., Tóth G., Tourwé D., Lebl M., Van Binst G., Hruby V.J. Synthesis. 000:1992;458.
38. Bailey P.D., Moore M.H., Morgen K.M., Smith D.I., Vernon J.M. Tetrahedron Lett. 35:1994;3587.
39. Kataoka Y., Seto Y., Yamamoto M., Yamada T., Kuwata S., Watanabe H. Bull. Chem. Soc. Japan. 49:1976;1081.
40. Hruby V.J., Tóth G., Gehrig C.A., Kao L.-F., Knapp R., Lui G.K., Yamamura H.I., Kramer T.H., Davis P., Burks T.F. J. Med. Chem. 34:1991;1823.
41. Mannekens E., Tourwé D., Vanderstichele S., Thi Diem T.N., Tóth G., Péter A., Chung N.N., Schiller P.W. Lett. Pept. Sci. 2:1995;190.
42. Abrash H.I., Niemann C. Biochemistry. 2:1963;947.
43. W. Solomon, J. Chem. Soc. (1947) 129.
44. Rastogi S.N., Bincha J., Anand N. Ind. J. Chem. 9:1971;1175.
45. Péter A., Laus G., Tourwé D., Gerlo E., Van Binst G. Pept. Res. 6:1993;48.