Enantiomeric and diastereomeric high-performance liquid chromatographic separation of cyclic β-substituted α-amino acids on a teicoplanin chiral stationary phase

Journal of Chromatography A

Volumn 868, Issue 2, 2000, Pages 197-207

  Schlauch, Michael ^a   Frahm, August W ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Amino acids, substituted; 1 Amino 2 hydroxycyclohexanecarboxylic acids; 1 Amino 2 methylcyclohexanecarboxylic acids; Chiral stationary phases, LC; Enantiomer separation

Indexed keywords

1 AMINO 2 HYDROXYCYCLOHEXANECARBOXYLIC ACID; 1 AMINO 2 METHYLCYCLOHEXANECARBOXYLIC ACID; TEICOPLANIN; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ORGANIC CHEMICALS; STEREOISOMERISM; TEICOPLANIN;

EID: 0033983449     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9673(99)01222-4     Document Type: Article

References (31)

1. R.D. Allan, J.R. Hanrahan, T.W. Hambley, G.A.R. Johnston, K.N. Mewett, A.D. Mitrovic, J. Med. Chem. 33 (1990) 2905.
2. Y. Gaoni, A.G. Chapman, N. Parvez, P.C.-K. Pook, D.E. Jane, J.C. Watkins, J. Med. Chem. 37 (1994) 4288.
3. T. Knöpfel, R. Kuhn, H. Allgeier, J. Med. Chem. 38 (1995) 1417.
4. N.J. Toms, P.J. Roberts, T.E. Salt, P.C. Straton, Trends Pharmacol. Sci. 17 (1996) 429.
5. F.C. Acher, F.J. Tellier, R. Azerad, I.N. Brabet, L. Fagni, J.-R Pin, J. Med. Chem. 40 (1997) 3119.
6. A. Breveglieri, R. Guerrini, S. Salvadori, C. Blanchi, S.D. Bryant, M. Attila, L.H. Lazarus, J. Med. Chem. 39 (1996) 773.
7. E. Gershonov, R. Granoth, E. Tzehoval, Y. Gaoni, M. Fridkin, J. Med. Chem. 39 (1996) 4833.
8. V.A. Davankov, in: J.C. Giddings, J. Cazes, PR. Brown (Eds.), Advances in Chromatography, Vol. 22, Marcel Dekker, New York, 1983, pp. 71-103.
9. V.A. Davankov, in: A.M. Krstulovic (Ed.), Chiral Separations by HPLC, Ellis Horwood, Chichester, 1989, pp. 446-475, Chapter 15.
10. T. Shinbo, T. Yamaguchi, K. Nishimura, M. Sugiura, J. Chromatogr. 405 (1987) 145.
11. P. Marfey, Carlsberg Res. Commun. 49 (1984) 591.
12. D.W. Aswad, Anal. Biochem. 137 (1984) 405.
13. R.H. Buck, K. Krummen, J. Chromatogr. 315 (1984) 279.
14. D.W. Armstrong, Y. Tang, S. Chen, Y. Zhou, C. Bagwill, J.-R. Chen, Anal. Chem. 66 (1994) 1473.
15. D.W. Armstrong, Y. Liu, K.H. Ekborgott, Chirality 7 (1995) 474.
16. A. Berthod, Y Liu, C. Bagwill, D.W. Armstrong, J. Chromatogr. A 731 (1996) 123.
17. A. Péter, G. Török, D.W. Armstrong, J. Chromatogr. A 793 (1998) 283.
18. A. Péter, G. Török, D.W. Armstrong, G. Tóth, D. Tourwé, J. Chromatogr. A 828 (1998) 177.
19. J.C.J. Barna, D.H. Williams, M.P. Williamson, J. Chem. Soc. Chem. Commun. 5 (1985) 254.
20. M.S. Westwell, U. Gerhard, D.H. Williams, J. Antibiot. 48 (1995) 1292.
21. D.H. Williams, Nat. Prod. Rep. 13 (1996) 469.
22. F.-J. Volk, A.W. Frahm, Liebigs Ann. Chem. (1996) 1893
23. K.P. Fondekar, F.-J. Volk, A.W. Frahm, Tetrahedron: Asymmetry 10 (1999) 727.
24. E. Weckert, G. Mattern, F.-J. Volk, A.W. Frahm, Acta Crystallogr. C 54 (1998) 387.
25. K.P. Fondekar, F.-J. Volk, E. Weckert, A.W. Frahm, Acta Crystallogr. C 55 (1999) 1167.
26. P.J. Schoenmakers, J.K. Strasters, A. Bartha, J. Chromatogr. 458 (1988) 355.
27. L.R. Snyder, J. Chromatogr. Sci. 16 (1978) 223.
28. P.H. Popieniek, R.F. Pratt, J. Am. Chem. Soc. 113 (1991) 2264.
29. Chirobiotic Handbook, Advanced Separation Technologies Inc., 2nd Edition, 1997.
30. F.P. Meyer, H. Walther, in: F. von Bruchhausen, G. Dannhardt, S. Ebel, A.W. Frahm, E. Hackenthal, U. Holzgrabe (Eds.), Hagers Handbuch der Pharmazeutischen Praxis, Vol. 9, Springer-Verlag, Berlin, 1994, p. 789.
31. Standard information for clinical pharmacists from Hoechst Marion Roussel, Bad Soden, Germany.