High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases

Journal of Chromatography A

Volumn 1232, Issue , 2012, Pages 142-151

  Sipos, László ^a   Ilisz, István ^b   Nonn, Melinda ^a   Fülöp, Ferenc ^a   Pataj, Zoltán ^b   Armstrong, Daniel W ^c   Péter, Antal ^b  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

Chirobiotic columns; Column liquid chromatography; Isoxazoline fused 2 aminocyclopentanecarboxylic acids; Macrocyclic glycopeptide based chiral stationary phases

Indexed keywords

AGLYCONES; ANALYTES; CHIRAL RECOGNITION; CHIRAL SELECTOR; CHIRAL STATIONARY PHASIS; COLUMN LIQUID CHROMATOGRAPHY; EFFECTS OF TEMPERATURE; ENANTIOMERIC SEPARATION; ENANTIOSEPARATIONS; MACROCYCLIC GLYCOPEPTIDES; MACROCYCLICS; MECHANISTIC ASPECTS; MOBILE-PHASE COMPOSITION; TEICOPLANIN; TEICOPLANIN AGLYCONE; TEMPERATURE RANGE; THERMODYNAMIC PARAMETER; VANCOMYCIN;

CHIRALITY; CHROMATOGRAPHY; ENANTIOMERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDES; PHASE COMPOSITION;

SEPARATION;

2 AMINOCYCLOPENTANECARBOXYLIC ACID; ISOXAZOLINE DERIVATIVE; POLYPEPTIDE ANTIBIOTIC AGENT; TEICOPLANIN; TEICOPLANIN AGLYCONE; UNCLASSIFIED DRUG; VANCOMYCIN AGLYCONE;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ELUTION; ENANTIOSELECTIVITY; ENTHALPY; EXPERIMENTAL DESIGN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOLEUCINE; ISOXAZOLES; LINEAR MODELS; STEREOISOMERISM; TEICOPLANIN; THERMODYNAMICS; VANCOMYCIN;

EID: 84858075154     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2011.11.027     Document Type: Article

References (44)

1. Hetényi A., Mándity I.M., Martinek T.A., Tóth G.K., Fülöp F. J. Am. Chem. Soc. 2005, 127:553.
2. Fülöp F., Martinek T.A., Tóth G.K. Chem. Soc. Rev. 2006, 35:323.
3. Kiss L., Forró E., Fülöp F. Synthesis of carbocyclic β-amino acids. Amino Acids, Peptides and Proteins in Organic Chemistry 2009, vol. 1:367. Wiley-VCH, Weinheim.
4. Kai H., Matsumoto H., Hattori N., Takase A., Fujiwara T., Sugimoto H. Bioorg. Med. Chem. Lett. 2001, 11:1997.
5. Basappa M., Sadashiva P., Mantelingu K., Swamy N.S., Rangappa K.S. Bioorg. Med. Chem. 2003, 11:4539.
6. Conti P., Caligiuri A., Pinto A., Roda G., Tamborini L., Nielsen B., Madsen U., Frydenvang K., Colombo A., De Micheli C. Eur. J. Med. Chem. 2007, 42:1059.
7. Pinto A., Conti P., De Amici M., Tamborini L., Grazioso G., Colleoni S., Mennini T., Gobbi M., De Micheli C. Tetrahedron: Asymmetry 2008, 19:867.
8. Chand P., Bantia S., Kotian P.L., El-Kattan Y., Lin T.-H., Babu Y.S. Bioorg. Med. Chem. 2005, 13:4071.
9. Chand P., Kotian P.L., Dehghani A., El-Kattan Y., Lin T.-H., Hutchison T.L., Babu Y.S., Bantia S., Elliot A.J., Montgomery J.A. J. Med. Chem. 2001, 44:4379.
10. Mineno T., Miller M.J. J. Org. Chem. 2003, 68:6591.
11. Ilisz I., Berkecz R., Péter A. J. Pharm. Biomed. Anal. 2008, 47:1.
12. D'Acquarica I., Gasparrini F., Misiti D., Zappia G., Cimarelli C., Palmieri G., Carotti A., Cellamare S., Villani C. Tetrahedron: Asymmetry 2000, 11:2375.
13. Ilisz I., Berkecz R., Péter A. J. Sep. Sci. 2006, 29:1305.
14. Péter A. J. Chromatogr. A 2002, 955:141.
15. Hyun M.H., Choi H.J., Kang B.S., Tan G., Choi Y.J. Bull. Korean Chem. Soc. 2006, 27:1775.
16. Hyun M.H., Song Y., Cho Y.J., Choi H.J. J. Sep. Sci. 2007, 30:2539.
17. Berkecz R., Sztojkov-Ivanov A., Ilisz I., Forró E., Fülöp F., Hyun M.H., Péter A. J. Chromatogr. A 2006, 1125:138.
18. Berkecz R., Ilisz I., Fülöp F., Pataj Z., Hyun M.H., Péter A. J. Chromatogr. A 2008, 1189:285.
19. Berkecz R., Ilisz I., Misicka A., Tymecka D., Fülöp F., Choi H.J., Hyun M.H., Peter A. J. Sep. Sci. 2009, 32:981.
20. Forró E. J. Chromatogr. A 2009, 1216:1025.
21. Wenzel T.J., Bourne C.E., Clark R.L. Tetrahedron: Asymmetry 2009, 20:2052.
22. Allenmark S., Schurig V. J. Mater. Sci. 1977, 7:1955.
23. Schurig V., Ossig J., Link R. Angew. Chem. 1989, 101:197.
24. Spanik I.I., Krupcik J., Schurig V. J. Chromatogr. A 1999, 843:123.
25. Fornstedt T., Sajonz P., Guichon G. J. Am. Chem. Soc. 1997, 119:1254.
26. Fornstedt T., Sajonz P., Guichon G. Chirality 1998, 10:375.
27. Gotmar G., Fornstedt T., Guiochon G. Anal. Chem. 2000, 72:3908.
28. Cavazzini A., Nadalini G., Dondi F., Gasparrini F., Ciogli A., Villani C. J. Chromatogr. A 2004, 1031:143.
29. Peyrin E., Guillaume Y.C., Guinchard C. Anal. Chem. 1997, 69:4979.
30. Kiss L., Nonn M., Forró E., Sillanpää R., Fülöp F. Tetrahedron Lett. 2009, 50:2605.
31. Forró E., Fülöp F. Tetrahedron: Asymmetry 2004, 15:2875.
32. Kiss L., Forró E., Sillanpää R., Fülöp F. J. Org. Chem. 2007, 72:8786.
33. Nonn M., Kiss L., Forró E., Mucsi Z., Fülöp F. Tetrahedron 2011, 67:4079.
34. Berthod A., Chen X., Kullman J.P., Armstrong D.W., Gasparrini F., D'Acquarica I., Villani C., Carotti A. Anal. Chem. 2000, 72:1767.
35. ÁRki A., Tourwé D., Solymár M., Fülöp F., Armstrong D.W., Péter A. Chromatographia 2004, 60:S43.
36. Péter A., ÁRki A., Vékes E., Tourwé D., Lázár L., Fülöp F., Armstrong D.W. J. Chromatogr. A 2004, 1031:171.
37. Sztojkov-Ivanov A., Lázár L., Fülöp F., Armstrong D.W., Péter A. Chromatographia 2006, 64:89.
38. Armstrong D.W., Liu Y., Ekborg-Ott K.H. Chirality 1995, 7:474.
39. Yao B., Zhan F., Yu G., Chen Z., Fan W., Zeng X., Zeng Q., Weng W. J. Chromatogr. A 2009, 1216:5429.
40. Balmér K., Lagerström P.O., Persson B.A. J. Chromatogr. 1992, 592:331.
41. Pirkle W.H., Murray P.G. J. High Resolut. Chromatogr. 1993, 16:285.
42. Schlauch M., Frahm A.W. Anal. Chem. 2001, 73:262.
43. Stringham R.W., Blackwell J.A. Anal. Chem. 1997, 69:1414.
44. Q2(R1) Document: Validation of Analytical Procedures: Text and Methodology, International Conference on Harmonization (ICH), Geneva, 2005.