Apparent and true enantioselectivity in enantioseparations

Chirality

Volumn 12, Issue 7, 2000, Pages 558-564

  Götmar, Gustaf ^a   Fornstedt, Torgny ^a   Guiochon, Georges ^b,c  

^a Department of Pharmacy ^*  (Sweden)

^b UNIVERSITY OF TENNESSEE   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

Apparent enantioselectivity; Enantioselectivity; Retention mechanisms; True nonselective interactions blockers

Indexed keywords

ALPRENOLOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; CELLULOSE 1,4 BETA CELLOBIOSIDASE; PROPRANOLOL;

ADSORPTION; ARTICLE; CHIRALITY; DRUG STRUCTURE; ENANTIOMER; EQUILIBRIUM CONSTANT; HYDROPHOBICITY; PH; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037844272     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/1520-636X(2000)12:7<558::AID-CHIR2>3.3.CO;2-U     Document Type: Article

References (25)

1. Anon. CHIRBASE Project. ENSSPICAM, Universite of Aix-Marseilles III, Marseilles, France.
2. Subramanian G. A practical approach to chiral separations by liquid chromatography. Weinheim: VCH Verlagsgesellschaft mbH; 1994.
3. Allenmark S. Chromatographic enantioseparation. Chichester, NY: Ellis Horwood; 1991.
4. Allenmark S, Andersson S. Proteins and peptides as chiral selectors in liquid chromatography. J Chromatogr A 1994;666:167-179.
5. 1-acid glycoprotein column. J Chromatogr 1985;325:379-384.
6. 1,-Acid glycoprotein chiral stationary phase. LC-GC 1986;4:422-430.
7. 1-acid glycoprotein. TrAc 1989;8:251-259.
8. Jacobson S, Golshan-Shirazi S, Guiochon G. Chromatographic band profiles and band separation of enantiomers at high concentration. J Am Chem Soc 1990;112:6492-6498.
9. Jacobsson S, Golshan-Shirazi S, Guiochon G. Isotherm selection for band profile simulations in preparative chromatography. AIChE J 1991; 37:836-844.
10. Pinkerton TC, Howe WJ, Ulrich EL, Comiskey JP, Haginaka J, Murashima T, Walkenhorst WF, Westler WM, Markley JL. Protein binding chiral discrimination of HPLC stationary phases made with whole, fragmented, and third domain turkey ovomucoid. Anal Chem 1995;67: 2354-2367.
11. Marie I, Erlandsson P, Hansson L, Isaksson R, Pettersson C, Pettersson G. Separation of enantiomers using cellulose (CBH I) silica as a chiral stationary phase. J Chromatogr 1991;586:233-248.
12. Isaksson R, Petterson C, Pettersom G, Jönsson S, Stålberg J, Hermansson J, Marie I. Cellulases as chiral selectors. TrAc 1994;13:431-438.
13. Fornstedt T, Zhong G, Bensetiti Z, Guiochon G. Experimental and theoretical study of the adsorption behavior and mass transfer kinetics of propranolol enantiomers on cellulase protein as the selector. Anal Chem 1996;68:2370-2378.
14. Fornstedt T, Sajonz P, Guiochon G. Thermodynamic study of an unusual chiral separation. Propranolol enantiomers on an immobilized cellulase. J Am Chem Soc 1997;119:1254-1264.
15. Fornstedt T, Götmar G. Andersson M, Guiochon G. Dependence on the mobile-phase pH of the adsorption behavior of propranolol enantiomers on a cellular protein used as the chiral selector. J Am Chem Soc 1999;121:1164-1174.
16. Götmar G, Fornstedt T, Andersson M, Guiochon G. Influence of solute hydrophobicity on the enantioselective adsorption of β-blockers on a cellulase protein used as the chiral selector. Anal chem, in press.
17. Fornstedt T, Sajonz P, Guiochon G. A closer study of chiral retention mechanisms. Chirality 1998;10:375-381.
18. Fornstedt T, Guiochon G. Modeling of chiral liquid chromatography using an immobilized protein as the selector. In: Lundahl P, Lundqvist A, Greijer E, editors. Quantitative analysis of biospecific interactions. Amsterdam: Harwood Academic Publishers, 1998.
19. Karger BL. New developments in chemical selectivity in gas-liquid chromatography. Anal Chem 1967;39:24A-50A.
20. Dobashi Y, Hara S. A chiral stationary phase derived from (R,R)-tartramide with broadened scope of application to the liquid chromatographic resolution of enantiomers. J Org Chem 1987;52:2490-2496.
21. Boehm DE, Martire DE, Armstrong DW. Theoretical considerations concerning the separation of enantiomeric solutes by liquid chromatography. Anal Chem 1988;60:522-528.
22. Schefzick S, Lindner W, Lipkowitz KB, Jalaie M. Enantiodiscrimination by a quinine-based chiral stationary phase: a computational study. Chirality 2000;12:7-15.
23. Jönsson S. Schön A, Isaksson R, Pettersson C, Pettersson G. An unexpected temperature effect obtained on enantiomer separation using CBH I-silica as a chiral stationary phase: increase in retention and enantioselectivity at elevated column temperature: a chromatographic and microcalorimetric study. Chirality 1992;4:505-508.
24. Henriksson H, Ståhlberg J, Isaksson R, Pettersson G. The active sites of cellulases are involved in chiral recognition: a comparison of cellobiohydrolase I and endogluanase I. FEBS Lett 1996;390:339-344.
25. Berthod A, Li W, Armstrong DW. Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas chromatographic chiral stationary phases. Anal Chem 1992;64:873-879.