Increments to chiral recognition facilitating enantiomer separations of chiral acids, bases, and ampholytes using Cinchona-based zwitterion exchanger chiral stationary phases

Journal of Separation Science

Volumn 35, Issue 13, 2012, Pages 1560-1572

  Wernisch, Stefanie ^a   Pell, Reinhard ^a   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Amino acid; Chiral stationary phase; Ion exchange; Liquid chromatography; Peptide; Zwitterion

Indexed keywords

ACID CHAINS; ACID SITE; AMPHOLYTES; ANALYTES; BASIC SITES; CATION EXCHANGERS; CHARGED FUNCTIONAL GROUPS; CHIRAL ACIDS; CHIRAL CENTERS; CHIRAL RECOGNITION; CHIRAL SEPARATIONS; CHIRAL STATIONARY PHASE; CHIRAL STATIONARY PHASIS; COUNTER-ION EFFECTS; ELUTION CONDITIONS; ELUTION ORDER; ENANTIOMER SELECTIVITY; ENANTIOMER SEPARATION; ENANTIOSEPARATIONS; FREE AMINO ACIDS; INTRAMOLECULAR DISTANCES; ION PAIRING; RETENTION TIME; SIDE-CHAINS; STATIONARY PHASIS; STERICALLY DEMANDING; ZWITTERION;

AMINO ACIDS; CHIRALITY; ENANTIOMERS; FUNCTIONAL GROUPS; ION EXCHANGE; ION EXCHANGERS; IONS; LIQUID CHROMATOGRAPHY; PEPTIDES;

STEREOCHEMISTRY;

ALKANESULFONIC ACID; AMPHOLYTE; CINCHONA ALKALOID; N [[( 6 METHOXYCINCHONAN 9 YL)OXY]CARBONYL] AMINOBUTANESULFONIC ACID; N [[( 6 METHOXYCINCHONAN 9 YL)OXY]CARBONYL] AMINOETHANESULFONIC ACID; N [[( 6 METHOXYCINCHONAN 9 YL)OXY]CARBONYL] AMINOPROPANESULFONIC ACID; N [[( 6 METHOXYCINCHONAN 9 YL]OXY]CARBONYL] AMINOETHANESULFONIC ACID; N [[( 6 METHOXYCINCHONAN9YL)OXY]CARBONYL] AMINOBUTANESULFONIC ACID; QUININE; UNCLASSIFIED DRUG;

ANION EXCHANGE; ARTICLE; CATION EXCHANGE; CHEMICAL STRUCTURE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL;

ACIDS; ADSORPTION; AMINO ACIDS; BUFFERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; CINCHONA ALKALOIDS; LEWIS BASES; STEREOISOMERISM;

CINCHONA;

EID: 84863681000     PISSN: 16159306     EISSN: 16159314     Source Type: Journal    
DOI: 10.1002/jssc.201200103     Document Type: Article

References (20)

1. Pasteur, L., C. R. Acad. Sci. 1858, XXXVII, 110.
2. Kaufman, T. S., Rúveda, E. A., Angew. Chem. Int. Ed. 2005, 44, 854-885.
3. Stork, G., Niu, D., Fujimoto, A., Koft, E. R., et al., J. Am. Chem. Soc. 2001, 123, 3239-3242.
4. Seeman, J. I., Angew. Chem. Int. Ed. 2007, 46, 1378-1413.
5. Smith, A. C., Williams, R. M., Angew. Chem. Int. Ed. 2008, 47, 1736-1740.
6. Christensen, B., J. Prakt. Chem. 1904, 193-227.
7. Hoffmann, H. M. R., Frackenpohl, J., in: Cinchona Alkaloids in Synthesis and Catalysis, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 2009, pp. 359-418.
8. Braje, W. M., Holzgrefe, J., Wartchow, R., Hoffmann, H. M. R., Angew. Chem. Int. Ed. 2000, 39, 2085-2087.
9. Lämmerhofer, M., Lindner, W., Adv. Chromatogr. 2008, 46, 1-107.
10. Lämmerhofer, M., J. Chromatogr. A 2010, 1217, 814-856.
11. Rosini, C., Bertucci, C., Pini, D., Altemura, P., Salvadori, P., Tetrahedron Lett. 1985, 26, 3361-3364.
12. Lämmerhofer, M., Lindner, W., J. Chromatogr. A 1996, 741, 33-48.
13. Mandl, A., Nicoletti, L., Lämmerhofer, M., Lindner, W., J. Chromatogr. A 1999, 858, 1-11.
14. Hoffmann, C. V., Pell, R., Lämmerhofer, M., Lindner, W., Anal. Chem. 2008, 80, 8780-8789.
15. Helberger, J. H., Manecke, G., Heyden, R., Liebigs Ann. Chem. 1949, 565, 22-35.
16. Helberger, J. H., Lantermann, H., Liebigs Ann. Chem. 1954, 586, 158-164.
17. Hoffmann, C. V., Lämmerhofer, M., Lindner, W., J. Chromatogr. A 2007, 1161, 242-251.
18. Hoffmann, C. V., Reischl, R., Maier, N. M., Lämmerhofer, M., Lindner, W., J. Chromatogr. A 2009, 1216, 1157-1166.
19. Maier, N. M., Nicoletti, L., Lämmerhofer, M., Lindner, W., Chirality 1999, 11, 522-528.
20. Kacprzak, K., Gawronski, J., in: Cinchona Alkaloids in Synthesis and Catalysis, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 2009, pp. 419-469.