Peak coalescence phenomena in enantioselective chromatography

Chirality

Volumn 10, Issue 1-2, 1998, Pages 140-146

  Schurig, Volker ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Chiral selectands; Chiral selectors; Enantiomer separation; Enantioselective chromatography; Peak coalescence

Indexed keywords

ARTICLE; CAPILLARY ELECTROPHORESIS; CATALYSIS; CHROMATOGRAPHY; ENANTIOMER; PRIORITY JOURNAL; TEMPERATURE DEPENDENCE;

EID: 0031950709     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.22     Document Type: Article

References (41)

1. Schurig, V. Molecular association in complexation gas chromatography. In: Chromatographic Separations Based on Molecular Recognition. Jinno, K., ed. New York: John Wiley, 1996:371-418.
2. Schurig, V., Bürkle, W. Extending the scope of enantiomer resolution by complexation gas chromatography. J. Am. Chem. Soc. 104:7573-7580, 1982.
3. Schurig, V., Betschinger, F. Metal-mediated enantioselective access to unfunctionalized aliphatic oxiranes: Prochiral and chiral recognition. Chem. Rev. 92:873-888, 1992.
4. Davankov, V. Separation of enantiomeric compounds using chiral HPLC systems. A brief review of general principles, advances, and development trends. Chromatographia 27:475-482, 1989.
5. Schurig, V. Gas chromatographic separation of enantiomers on optically active metal-complex-free stationary phases. Angew. Chem. Int. Ed. Engl. 23:747-765, 1984.
6. Gil-Av, E. Present status of enantiomeric analysis by gas chromatography. J. Mol. Evol. 6:131-144, 1975.
7. Koppenhoefer, B., Nothdurft, A., Pierrot-Sanders, J., Piras, P., Popescu, C., Roussel, C., Stiebler, M., Trettin, U. CHIRBASE, a graphical molecular database on the separation of enantiomers by liquid-, supercritical fluid-, and gas chromatography. Chirality 5:213-219, 1993.
8. Eliel, E.L., Wilen, S.H., Mander, L.N. Stereochemistry of Organic Compounds. New York: John Wiley, 1994:1075.
9. Schurig, V. In: Houben-Weyl, Methods of Organic Chemistry, Vol. E 21a, Stereoselective Synthesis, p. 167.
10. Levin, S., Stein, M., Magora, A. Structural features affecting the resolution of enantiomers of antiviral substances. Abstracts of the 7th Int. Symp. Chiral Discrimination, Jerusalem, 1995, p. 8.
11. Roussel, C., J.-L. Stein, J.-L., Beauvais, F., Chemlal, A. Example of the concentration dependence of elution order in the resolution of enantiomers on microcrystalline triacetylcellulose chiral stationary phase. J. Chromatogr. 462:95-103, 1989.
12. Schmitt, T., Engelhardt, H. Charged and uncharged cyclodextrins as chiral selectors in capillary electrophoresis, Chromatographia 37:475-481, 1993.
13. Chankvetadze, B. Nature and design of enantiomer migration order in chiral capillary electrophoresis. Proceedings Symposium Molecular Chirality, Tokyo, Japan, 1996, p. 39.
14. Chankvetadze, B., Schulte, G., Blaschke, G. Nature and design of enantiomer migration order in chiral capillary electrophoresis. Enantiomer 2:157-179, 1997.
15. Schurig, V. Resolution of a chiral olefin by complexation chromatography on an optically active rhodium (I) complex. Angew. Chem., Int. Ed. Engl. 16:110, 1977.
16. Raban, M., Mislow, K. Modern methods for the determination of optical purity. Top. Stereochem. 2:199-230, 1967.
17. Beitler, U., Feibush, B. Interaction between asymmetric solutes and solvents: Diamides derived from L-valin as stationary phases in gas-liquid partition chromatography. J. Chromatogr. 123:149-166, 1976.
18. Noyori, R., Kitamura, M. Enantioselective addition of organometallic reagents to carbonyl compounds. Chirality transfer, multiplication and amplification. Angew. Chem. Int. Ed. Engl. 30:49-69, 1991.
19. Welch, C.J. Imprintable brush-type chiral stationary phase. J. Chromatogr. 689:189-193, 1995.
20. Pirkle, W.H., Daeppen, R., Reno, D.S. Applications for racemic versions of chiral stationary phases. J. Chromatogr. 407:211-216, 1987.
21. Reist, M., Testa, B., Carrupt, P.-A., Jung, M., Schurig, V. Racemization, enantiomerization, diastereomerization, and epimerization: Their meaning and pharmacological significance. Chirality 7:396-400, 1995.
22. Mannschreck, A., Zinner, H., Pustet, N. The significance of the HPLC time scale: An example of interconvertable enantiomers. Chimia 43: 165-166, 1989.
23. Bürkle, W., Karfunkel, H., Schurig, V. Dynamic phenomena during enantiomer resolution by complexation gas chromatography: A study of enantiomerization. J. Chromatogr. 288:1-14, 1984.
24. Jung, M., Schurig, V. Determination of enantiomerization barriers by computer simulation of interconversion profiles: Enantiomerization of diaziridines during chiral inclusion gas chromatography. J. Am. Chem. Soc. 114:529-534, 1992.
25. Schurig, V., Jung, M., Schleimer, M., Klärner, F.-G. Investigation of the enantiomerization barrier of homofuran by computer simulation of interconversion profiles obtained by complexation gas chromatography. Chem. Ber. 125:1301-1303, 1992.
26. Veciana, J., Crespo, M.J. Dynamic HPLC: A method for determining rate constants, energy barrier, and equilibrium constants of molecular dynamic processes. Angew. Chem. Int. Ed. Engl. 30:74-76, 1991.
27. Kirkland, K.M., McCombs, D.A. Changes in chiral selectivity with temperature for an ovomucoid protein-based column. J. Chromatogr. 666:211-219, 1994.
28. Gasparrini, F., Lunazzi, L., Misiti, D., Villani, C. Organic stereochemistry and conformational analysis from enantioselective chromatography and dynamic nuclear magnetic resonance measurements. Acc. Chem. Res. 28:163-170, 1995.
29. Schurig, V., Nowotny, H.-P., Schmalzing, D. Gas-chromatographic enantiomer separation of unfunctionalized cycloalkanes on permethylated β-cyclodextrin. Angew. Chem. Int. Ed. Engl. 28:736-737, 1989.
30. Nowotny, H.-P. Enantiomerentrennung durch Inklusions-Gaschromatographie an peralkylierten Cyclodextrinen. PhD Thesis, University Tübingen, 1989.
31. Koppenhoefer, B., Bayer, E. Chiral recognition in the resolution of enantiomers by glc. Chromatographia 19:123-130, 1984.
32. Watabe, K., Charles, R., Gil-Av, E. Temperature-dependent reversal of the elution order during the separation of α-amino acid enantiomers on chiral diamide selectors. Angew. Chem. Int. Ed. Engl. 28:192-193, 1989.
33. Schurig, V., Ossig, J., Link, R. Evidence for a temperature dependent reversal of the enantioselectivity in complexation gas chromatography on chiral phases. Angew. Chem. Int. Ed. Engl. 28:194-196, 1989.
34. Laderer, H. Moderne Enantiomeranalytik durch Komplexierungs-Gaschromatographie und Kernresonanz-Spektroskopie. Nickel (II)- und Europium(III)-Chelate 3-acylierter Campherderivate. PhD Thesis, University Tübingen, 1990.
35. Hess, H., Burger, G., Musso, H. Complete enantiomer separation by chromatography on starch. Angew. Chem. Int. Ed. Engl. 17:612-614, 1978.
36. Mayer, S., Schleimer, M., Schurig, V. Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis. J. Microcol. Sep. 6:43-48, 1994.
37. Pettersson, C., Gioeli, G. Improved resolution of enantiomers of naproxen by the simultaneous use of a chiral stationary phase and a chiral additive in the mobile phase. J. Chromatogr. 435:225-228, 1988.
38. Duff, K.J., Gray, H.L., Gray, R.J., Bahler, C.C. Chiral stationary phases in concert with homologous chiral mobile phase additives: Push/pull model. Chirality 5:201-206, 1993.
39. Schurig, V., Juza, M., Grosenick, H. Enantiomer separation of chiral inhalation anesthetics (enflurane, isoflurane and desflurane) by gas chromatography on a γ-cyclodextrin derivative. Recl. Trav. Chim. Pays-Bas 114:211-219, 1995.
40. Kimata, K., Hosoya, K. Araki, T., Tanaka, N. Direct chromatographic separation of racemates on the basis of isotopic chirality. Anal. Chem. 69:2610-2612, 1997.
41. Pirkle, W., Gan, K.Z. A direct chromatographic separation of enantiomers chiral by virtue of isotopic substitution. Tetrahedron: Asymm. 8:811-814, 1997.