Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase

Chirality

Volumn 10, Issue 5, 1998, Pages 434-483

  Ekborg Ott, K Helen ^a   Liu, Youbang ^a   Armstrong, Daniel W ^a  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

Author keywords

Chiral stationary phase; Enantiomeric separations; Macrocyclic antibiotic; Ristocetin A; Underivatized amino acids

Indexed keywords

DIPEPTIDE; MACROLIDE; RISTOCETIN A; SILICA GEL; TEICOPLANIN; TRIPEPTIDE; VANCOMYCIN;

ARTICLE; CHIRALITY; COVALENT BOND; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE ANALYSIS; PRIORITY JOURNAL; RACEMIC MIXTURE;

ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MODELS, MOLECULAR; PROTEIN CONFORMATION; RISTOCETIN; STEREOISOMERISM;

EID: 0031828171     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>3.0.CO;2-0     Document Type: Article

References (32)

1. 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. 66:1473-1484, 1994.
2. Armstrong, D.W., Liu, Y., Ekborg-Ott, K.H. A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations. Chirality 7:474-497, 1995.
3. Berthod, A., Liu, Y., Bagwill, C., Armstrong, D.W. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J. Chromatogr. A 731:123-137, 1996.
4. Chen, S., Liu, Y., Armstrong, D.W., Victory, P., Borrell, J.I., Martinez-Teipel, B., Matallana, J.L. Enantioresolution of substituted 2-methoxy-6-oxo-1,4,5.6-tetrahydropyridine-3-carbonitriles on macrocyclic antibiotic and cyclodextrin stationary phases. J. Liq. Chromatogr. 18:1495-1507, 1995.
5. Berthod, A., Nair, U.B., Bagwill, C., Armstrong, D.W. Derivatized vancomycin stationary phases for LC chiral separations. Talanta 43:1767-1782, 1996.
6. Armstrong, D.W., Zhou, E.Y. Use of a macrocyclic antibiotic as a chiral selector for enantiomeric separations by TLC. J. Liq. Chromatogr. 17: 1695-1707, 1994.
7. Armstrong, D.W., Rundlett, K.L., Reid III, G.L. Use of a macrocyclic antibiotic, rifamycin B, and indirect detection for the resolution of racemic amino alcohols by CE. Anal. Chem. 66:1690-1695, 1994.
8. Armstrong, D.W., Rundlett, K.L., Chen, J.-R. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis. Chirality 6:496-509, 1994.
9. Rundlett, K.L., Gasper, M.P., Zhou, E.Y., Armstrong, D.W. Capillary electrophoretic enantiomeric separations using the glycopeptide antibiotic, teicoplanin. Chirality 8:88-107, 1996.
10. Armstrong, D.W., Rundlett, K.L. CE resolution of neutral and anionic racemates with glycopeptide antibiotics and micelles. J. Liq. Chromatogr. 18:3659-3674, 1995.
11. Gasper, M.P., Berthod, A. Nair, U.B., Armstrong, D.W. Comparison and modelling study of vancomycin, ristocetin A and teicoplanin for CE enantioseparations. Anal. Chem. 68:2501-2514, 1996.
12. Armstrong, D.W., Gasper, M.P., Rundlett, K.L. Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A J. Chromatogr. A 689:285-304, 1995.
13. Ward, T.J. Chiral media for capillary electrophoresis. Anal. Chem. 66: 633A-640A, 1994.
14. Ward, T.J., Dann III, C., Blaylock, A. Enantiomeric resolution using the macrocyclic antibiotic rifamycin B and rifamycin SV as chiral selectors for capillary electrophoresis. J. Chromatogr. A 715:337-344, 1995.
15. Rundlett, K.L., Armstrong, D.W. Effects of micelles and mixed micelles on efficiency and selectivity of antibiotic-based capillary electrophoretic enantioseparations. Anal. Chem. 67:2088-2095, 1995.
16. Ward, T.J., Dann III, C., Brown, A.P. Separation of enantiomers using vancomycin in a countercurrent process by suppression of electroosmosis. Chirality 8:77-83, 1996.
17. Vespalec, R., Corstjens, H., Billiet, H.A.H., Frank, J., Luyhen, K.Ch.A.M. Enantiomeric separation of sulfur-and selenium-containing amino acids by capillary electrophoresis using vancomycin as a chiral selector. Anal. Chem. 67:3223-3228, 1995.
18. Lüttringhaus, A., Gralheer, H. Über eine neue Art atropisomerer Verbindungen. Justus Liebigs Ann. Chim. 550:67-98, 1942.
19. Philip, J.E., Schenck, J.R., Hargie, M.P. Ristocetins A and B, two new antibiotics. Isolation and properties. Antibiot. Annu. (New York: Medical Encyclopedia, Inc., 1957) 699-705, 1956-1957.
20. Romansky, M.J., Limson, B.M., Hawkins, J.E. Ristocetin: A new antibiotic. Laboratory and clinical studies. Preliminary report. Antibiot. Annu. (New York: Medical Encyclopedia, Inc., 1957) 706-715, 1956-1957.
21. Jordan, D.C. Ristocetin. In: Antibiotics, Vol. 1. Gottlieb, D., Shaw, P., eds. New York: Springer, 1967:84-89.
22. Nieto M., Perkins, H.R. Modifications of the acyl-D-alanine terminus affecting complex-formation with vancomycin. Biochem. J. 123:789-803, 1971
23. Boger, D.L., Nomoto, Y., Teegarden, B.R. Vancomycin and ristocetin models: Synthesis via the Ullman macrocyclization reaction. J. Org. Chem. 58:1425-1433, 1993.
24. Lichtenstein, N. Preparation of γ-alkylamideS of glutamic acid. J. Am. Chem. Soc. 64:1021-1022, 1942.
25. Ekborg-Ott, K.H., Armstrong, D.W., Taylor, A. Varietal differences in the total and enantiomeric composition of theanine in tea. J. Agric. Food Chem. 45:353-363, 1997.
26. Carpino, L.A., Cohen, B.J., Stephens, Jr., K.E., Sadat-Aalaee, S.Y., Tien, J.H., Langridge, D.C. ((9-Fluorenylmethyl)oxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and applications to the rapid synthesis of short peptide segments. J. Org. Chem. 51:3732-3734, 1986.
27. Armstrong, D.W., Li, W. Optimization of liquid chromatographic separations on cyclodextrin-bonded phases. Chromatography 2:43-48, 1987.
28. Han, S., Armstrong, D.W. In: HPLC Separations of Enantiomers and Other Isomers With Cyclodextrin Bonded Phases: Rules for Chiral Recognition in Chiral Separations by HPLC. Krustlovic, A.M. ed. West Sussex: Ellis Horwood, Ltd., 1989:208-286.
29. Armstrong, D.W., Chen, S., Chang, D., Chang, S. A new approach to the direct resolution of racemic beta adenergic blocking agents by HPLC. J. Liq. Chromatogr. 15:545-556, 1992.
30. Chang, S.C., Reid III, G.L., Chen, S., Chang, C.D., Armstrong, D.W. Evaluation of a new polar-organic high-performance liquid chromatographic mobile phase for cyclodextrin bonded chiral stationary phases. Trends Anal. Chem. 12:144-153, 1993.
31. Pawlowska, M., Chen, S., Armstrong, D.W. Enantiomeric separation of fluorescent 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) tagged amino acids. J. Chromatogr. 641:257-265, 1993.
32. Armstrong, D.W. The evolution of chiral stationary phases for liquid chromatography. LC · GC Current Issues in HPLC May (Suppl.):S20-S28, 1997.