Chromatographic enantioseparation of amino acids using a new chiral stationary phase based on a macrocyclic glycopeptide antibiotic

Journal of Separation Science

Volumn 29, Issue 10, 2006, Pages 1447-1457

  Petrusevska, Katerina ^a   Kuznetsov, Mikhail A ^b   Gedicke, Knut ^c   Meshko, Vera ^a   Staroverov, Sergey M ^b   Seidel Morgenstern, Andreas ^c,d  

^a SS CYRIL AND METHODIUS UNIVERSITY   (Macedonia)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c OTTO VON GUERICKE UNIVERSITY   (Germany)

^d MAX PLANCK INSTITUTE FOR DYNAMICS OF COMPLEX TECHNICAL SYSTEMS   (Germany)

Author keywords

Amino acids; Chromatographic enantioseparation; Eremomycin; Macrocyclic glycopeptide antibiotics

Indexed keywords

ADSORPTION ISOTHERMS; ANTIBIOTICS; CHROMATOGRAPHY; COMPOSITION; SEPARATION; TEMPERATURE;

CHIRAL STATIONARY PHASE; CHROMATOGRAPHIC ENANTIOSEPARATION; EREMOMYCIN; MACROCYCLIC GLYCOPEPTIDE ANTIBIOTICS;

AMINO ACIDS;

AMINO ACID; ASPARAGINE; EREMOMYCIN; GLUTAMINE; LEUCINE; MACROCYCLIC COMPOUND; METHIONINE; POLYPEPTIDE ANTIBIOTIC AGENT; SERINE; SILICON DIOXIDE; TEICOPLANIN; VALINE;

ADSORPTION; ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; CONTROLLED STUDY; DRUG STRUCTURE; ELUTION; ENANTIOMER; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; EXPERIMENTAL MODEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTHERM; MATHEMATICAL ANALYSIS; POROSITY; PREDICTION; PRIORITY JOURNAL; SEPARATION TECHNIQUE; VALIDATION PROCESS;

ADSORPTION; AMINO ACIDS; ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOPEPTIDES; MACROCYCLIC COMPOUNDS; MATERIALS TESTING; MATHEMATICS; MOLECULAR STRUCTURE; POROSITY; STEREOISOMERISM; TEICOPLANIN;

EID: 33746393173     PISSN: 16159306     EISSN: 16159314     Source Type: Journal    
DOI: 10.1002/jssc.200600036     Document Type: Article

References (64)

1. Franco, P., Minguillón, C., in: Chiral Separation Techniques-A Practical Approach, G. Subramanian (Eds.), Wiley-VCH, Weinheim 2001, pp. 1-23.
2. Maier, N. M., Franco, P., Lindner, W., J. Chromatogr. A 2001, 906, 3-33.
3. Ahuja, S. (Eds.), Chiral Separations, Applications and Technology, American Chemical Society, Washington DC 1997.
4. Davankov, V. A., J. Chromatogr. A 1994, 666, 55-76.
5. Oi, N., Kitahara, H., Aoki, F., J. Chromatogr. A 1995, 707, 380-383.
6. Schlauch, M., Volk, F. J., Fondekar, K. P., Wede, J., Frahm, A. W., J. Chromatogr. A 2000, 897, 145-152.
7. Schlauch, M., Frahm, A. W., Anal. Chem. 2001, 73, 262-266.
8. Davankov, V. A., J. Chromatogr. A 2003, 1000, 891-915.
9. Armstrong, D. W., DeMond, W., J. Chromatogr. Sci. 1984, 22, 411-415.
10. Armstrong, D. W., Ward, T. J., Armstrong, R. D., Beesley, T. E., Science 1986, 232, 1132-1135.
11. Armstrong, D. W., Stalcup, A. M., Hilton, M. L., Duncan, J., et al., Anal. Chem. 1990, 62, 1610-1615.
12. Ryu, J. W., Kim, D. W., Lee, K. P., Pyo, D., Park, J. H., J. Chromatogr. A 1998, 814, 247-252.
13. Warnke, M. M., Mitchell, C. R., Rozhkov, R. V., Emrich, D. E., et al., J. Liq. Chromatogr. R. T. 2005, 28, 823-834.
14. Okamoto, Y., Kawashima, M., Hatada, K., J. Am. Chem. Soc. 1984, 106, 5357-5359.
15. Aboul-Enein, H. Y., J. Chromatogr. A 2001, 906, 185-193.
16. Felix. G., J. Chromatogr. A 2001, 906, 171-184.
17. Franco, P., Senso, A., Oliveros, L., Minguillon, C., J. Chromatogr. A 2001, 906, 155-170.
18. Yashima, E., J. Chromatogr. A 2001, 906, 105-125.
19. Chankvetadze, B., Kartozia, I., Yamamoto, C., Okamoto, Y., J. Pharm. Biomed. Anal. 2002, 27, 467-478.
20. Ikai, T., Yamamoto, C., Kamigaito, M., Okamoto, Y., Chirality 2005, 17, 299-304.
21. Kubota, T., Yamamoto, C., Okamoto, Y., Chirality 2003, 15, 77-82.
22. Chankvetadze, B., Ikai, T., Yamamoto, C., Okamoto, Y., J. Chromatogr. A 2004, 1042, 55-60.
23. Hyun, M. H., Jin, J. S., Lee, W. J., J. Chromatogr. A 1998, 822, 155-161.
24. Hyun, M. H., Han, S. C., Lipshutz, B. H., Shin, Y. J., Welch, C. J., J. Chromatogr. A 2001, 910, 359-365.
25. Hyun, M. H., Jin, J. S., Han, S. C., Cho, Y. J., Microchem. J. 2001, 70, 205-209.
26. Stenberg, M., Marko-Varga, G., Oste, R., Food Chem. 2002, 79, 507-512.
27. Lämmerhofer, M., Lindner, W., J. Chromatogr. A 1996, 741, 33-48.
28. Oberleitner, W. R., Maier, N. M., Lindner, W., J. Chromatogr. A 2002, 960, 97-108.
29. Czerwenka, C., Lämmerhofer, M., Lindner, W., J. Sep. Sci. 2003, 26, 1499-1508.
30. Lubda, D., Lindner, W., J. Chromatogr. A 2004, 1036, 135-143.
31. Armstrong, D. W., Tang, Y. B., Chen, S. S., Zhou, Y. W., et al., Anal. Chem. 1994, 66, 1473-1484.
32. Berthod, A., Chen, X., Kullman, J. P., Armstrong. D. W., et al., Anal. Chem. 2000, 72, 1767-1780.
33. Chirobiotic Handbook, Advanced Separation Technologies Inc. 1999.
34. Ward, T. J., Farris III, A. B., J. Chromatogr. A 2001, 906, 73-89.
35. Gauze, G. F., Brazhnikova, M. G., Laiko, A. V., Sveshnikova, M. A., Preobrazhenskaia, T. P., Antibiot. Med. Biotekhnol. 1987, 32, 571-576.
36. Gauze, G. F., Brazhnikova, M. G., Lomakina, N. N., Berdnikova, T. F., et al., J. Antibiot. 1989, 42, 1790-1797.
37. Cavazzini, A., Nadalini, G., Dondi, F., Gasparrini, F., et al., J. Chromatogr. A 2004, 1031, 143-158.
38. Berthod, A., Liu, Y. B., Bagwill, C., Armstrong, D. W., J. Chromatogr. A 1996, 731, 123-137.
39. Peter, A., Torok, G., Armstrong, D. W., J. Chromatogr. A 1998, 793, 283-296.
40. Tesarova, E., Bosakova, Z., Pecakova, V., J. Chromatogr. A 1999, 838, 121-129.
41. Peter, A., Olajos, E., Casimir, R., Tourwe, D., et al., J. Chromatogr. A 2000, 871, 105-113.
42. Schlauch, M., Frahm, A. W., J. Chromatogr. A 2000, 868, 197-207.
43. Jandera, P., Skavrada, M., Klemmova, K., Backovska, V., Guiochon, G., J. Chromatogr. A 2001, 917, 123-133.
44. Xiao, T. L., Zhang, B., Lee, J. T., Hui, F., Armstrong, D. W., J. Liq. Chromatogr. R. T. 2001, 24, 2673-2684.
45. Hrobonova, K., Lehotay, J., Cizmarikova, R., Armstrong, D. W., J. Liq. Chromatogr. R. T. 2001, 24, 2225-2237.
46. Rojkovicova, T., Lehotay, J., Dungelova, J., Cizmarik, J., Armstrong. D. W., J. Liq. Chromatogr. R. T. 2002, 25, 2723-2738.
47. Lomakina, N. N., Berdnikova, T. F., Tokareva, N. L., Abramova, E. A., Dokshina, N. Y., Antibiot. Khimioterap. 1989, 34, 254-258.
48. Polyakova, I. V., Kolikov, V. M., Pisarev, O. A., J. Chromatogr. A 2003, 1006, 251-260.
49. D'Acquarica, I., J. Pharm. Biomed. Anal. 2000, 23, 3-13.
50. Russia Patent Nr. 2004118276, 2004.
51. Staroverov, S. M., Kuznetsov, M. A., Nesterenko, P. N., Vasiarov, et al., J. Chromatogr. A 2006, 1108, 263-267.
52. Guiochon, G., Golshan-Shirazi, S., Katti, A. M., Preparative and nonlinear chromatography, Academic Press, Boston 1994.
53. Guiochon, G., J. Chromatogr. A 2002, 965, 129-161.
54. Nicoud, R. M., Seidel-Morgenstern, A., Isolation and Purification 1996, 2, 165-200.
55. Golshan-Shirazi, S., Guiochon, G., J. Chromatogr. A 1994, 658, 149-171.
56. Rouchon, P., Schonauer, M., Valentin, P., Guiochon, G., Sep. Sci. Technol. 1987, 22, 1793-1833.
57. Seidel-Morgenstern, A., J. Chromatogr. A 2004, 1037, 255-272.
58. Guan, H., Stanley, B. J., Guiochon, G., J. Chromatogr. A 1994, 659, 27-41.
59. Miyabe, K., Khattabi, S., Cherrak, D. E., Guiochon, G., J. Chromatogr. A 2000, 872, 1-21.
60. Ravald, L., Fornstedt, T., J. Chromatogr. A 2001, 908, 111-130.
61. Shan, Y., Seidel-Morgenstern, A., J. Chromatogr. A 2004, 1041, 53-62.
62. Felinger, A., Guiochon, G., J. Chromatogr. A 1996, 752, 31-40.
63. Blehaut, J., Nicoud, R. M., Analusis 1998, 26, M60-M70.
64. Lorenz, H., Sheehan, P., Seidel-Morgenstern, A., J. Chromatogr. A 2001, 908, 201-214.