A closer study of chiral retention mechanisms

Chirality

Volumn 10, Issue 5, 1998, Pages 375-381

  Fornstedt, Torgny ^a   Sajonz, Peter ^b,c   Guiochon, Georges ^b,c  

^a UPPSALA UNIVERSITY   (Sweden)

^b UNIVERSITY OF TENNESSEE   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

Bonding; Chiral stationary phases; Equilibrium isotherms; Retention mechanisms; Separation of enantiomers

Indexed keywords

4 METHYLCELLULOSE TRIBENZOATE; BOVINE SERUM ALBUMIN; CELLULOSE 1,4 BETA CELLOBIOSIDASE; CELLULOSE DERIVATIVE; KETOPROFEN; PROPRANOLOL; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; CHEMICAL BOND; CHIRAL CHROMATOGRAPHY; DRUG DETERMINATION; ENANTIOMER; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; TRANSPORT KINETICS;

EID: 0031875895     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:5<375::AID-CHIR3>3.0.CO;2-5     Document Type: Article

References (41)

1. Armstrong, D.W., Han, S.M. Enantiomeric separations in chromatography. C.R.C. Crit. Rev. Anal. Chem. 19:175, 1988.
2. Pirkle, W.H., Pochapsky, T.C. Considerations of chiral recognition relevant to the liquid chromatographic separations of enantiomers. Chem. Rev. 89:347, 1989.
3. Allenmark, S. Chromatographic Enantioseparation, 2nd ed. Chichester, NY: Ellis Horwood, 1991:129.
4. Gil-Av, E.J. Present status of enantiomeric analysis by gas chromatography. Mol. Evol. 6:131, 1975.
5. Watanabe, T., Charles, Gil-Av, E. Temperature dependent inversion of elution sequence in the resolution of ct-amino acid enantiomers on chiral diamide selectors. Angew. Chem. (int ed.), 28:192, 1989.
6. Anon. CHIRBASE Project. ENSSPICAM, University of Aix-Marseilles III, Marseilles, France.
7. Jacobson, S.C., Golshan-Shirazi, S., Guiochon, G. Chromatographic band profiles and band separation of optical isomers at high concentration. J. Am. Chem. Soc. 112:6492, 1990.
8. Charton, F., Guiochon, G. Modeling of the adsorption behavior and the chromatographic band profiles of enantiomers. Behavior of methyl mandelate on immobilized cellulose. J. Chromatogr. 630:21, 1993.
9. Fornstedt, T., Sajonz, P., Guiochon, G. Thermodynamic study of an unusual chiral separation, propranolol enantiomers on an immobilized cellulase. J. Am. Chem. Soc. (in press).
10. Dalgliesh, C.E. Optical resolution of aromatic amino acids on paper chromatograms. J. Chem. Soc. 3940, 1952.
11. Dalgliesh, C.E. J. Chem. Soc. 363, 1974.
12. Pirkle, W.H., Finn, J. Chiral high-pressure liquid chromatographic stationary phases. J. Org. Chem. 46:2935, 1981.
13. Pirkle, W.H. Stacking of amide dipoles as an alternative to hydrogen bonds in chiral recognition rationales. Tetrahedron Lett. 24:5707, 1983.
14. Jaroniec, M., Madey, R. Physical Adsorption on Heterogeneous Solids. Amsterdam: Elsevier, 1988.
15. Rudzinski, W., Everett, D.H. Adsorption of Gases on Heterogeneous Surfaces. New York: Academic Press, 1992.
16. Welch, C. Evolution of chiral stationary phase design in the Pirkle laboratories. J. Chromatogr. A 666:3, 1994.
17. Allenmark, S., Bomgren, B., Boren, H. Direct resolution of enantiomers by liquid affinity chromatography on albumin agarose under isocratic conditions. J. Chromatogr. 237:473, 1982.
18. Allenmark, S., Bomgren, B. Direct chromatographic separation of enantiomers on immobilized protein stationary phases. II. Optical resolution of a sulphoxide, a sulphoximide and a benzoyl amino acid. J. Chromatogr. 252:297, 1982.
19. Hermansson, J.L.E. Direct liquid chromatographic resolution of racemic drugs using α acid glycoprotein as the chiral stationary phase. J. Chromatogr, 269:71, 1983.
20. Allenmark, S., Andersson, S. Proteins and peptides as chiral recognition selectors in liquid chromatography. J. Chromatogr. A 666:167, 1994.
21. Langmuir, I. The constitution and fundamental properties of solids and liquids. J. Am. Chem. Soc. 38:2221, 1916.
22. Booth, T.D., Wainer, I.W. Investigation of the enantioselective separations of α-alkylaryl-carboxylic acids on an amylose tris (3,5-dimethylphenylcarbamate) chiral stationary phase using quantitative structure-enantioselective retention relationships. Identification of a conformationally driven chiral recognition mechanism. J. Chromatogr. 737:157, 1996.
23. Vandenbosch, C., Massart, D.L., Lindner, W. Evaluation of the enantioselectivity of an ovomucoid and a cellulase chiral stationary phase toward a set of β-blocking agents. Anal. Chim. Acta. 270:1, 1992.
24. 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. 68:2370, 1996.
25. Andrade, J.D. In: Surface and Interfacial Aspects of Biomedical Polymers, vol. 60. Andrade, J.D., ed. New York: Plenum Press, 1985.
26. Guiochon, G., Shirazi, S.G., Katti, A.M. Fundamentals of Preparative and Nonlinear Chromatography. Boston: Academic Press, 1994.
27. Graham, D. The characterization of physical adsorption systems: I. The equilibrium function and standard free energy of adsorption. J. Phys. Chem. 57:665, 1953.
28. Laub, R.J. Manner of sorption and form of the sorption isotherm in gas, liquid, and ion-exchange chromatography. ACS Symp. Ser. 297:1, 1986.
29. 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 4:505, 1992.
30. Jacobson, S.C., Golshan-Shirazi, S., Guiochon, G. Isotherm selection for band profile simulations in preparative chromatography. AIChE J., 37:836, 1991.
31. Jacobson, S.C., Guiochon, G. Experimental study of the production rate of pure enantiomers from a racemic mixture by preparative chromatography. J. Chromatogr. 590:119, 1992.
32. Charton, F., Bailly, M., Guiochon, G. Recycling in preparative liquid chromatography. J. Chromatogr. A. 687:13, 1994.
33. Jacobson, S.C., Seidel-Morgenstern, A., Guiochon, G. Study of band broadening in enantio-selective separations using microcrystalline cellulose triacetate. I. The linear case. J. Chromatogr. 637:13, 1993.
34. Seidel-Morgenstern, A., Jacobson, S.C., Guiochon, G. Study of band broadening in enantio-selective separations using microcrystalline cellulose triacetate. II. Frontal analysis. J. Chromatogr. 637:19, 1993.
35. Seidel-Morgenstern, A., Guiochon, G. Modeling of the competitive isotherms and the chromatographic separation of two enantiomers. Chem. Eng. Sci. 48:2787, 1993.
36. Seidel-Morgenstern, A., Guiochon, G. Thermodynamics of the adsorption of Tröger's base enantiomers from ethanol on cellulose triacetate. J. Chromatogr. 631:37, 1993.
37. Jacobson, S.C., Andersson, S., Allenmark, S.G., Guiochon, G. Estimation of the number of enantioselective sites of bovine serum albumin using frontal chromatography. Chirality 5:513, 1993.
38. Fornstedt, T., Zhong, G., Guiochon, G. Peak tailing and mass transfer kinetics in linear chromatography. J. Chromatogr. A 741:1, 1996.
39. Fornstedt, T., Zhong, G., Guiochon, G. Peak tailing and slow mass transfer kinetics in nonlinear chromatography. J. Chromatogr. A 742: 55, 1996.
40. Jacobson, S.C., Golshan-Shirazi, S., Guiochon, G. Measurement of the heats of adsorption for chiral isomers on an enantioselective stationary phase. J. Chromatogr. 522:23, 1990.
41. Jacobson, S.C., Guiochon, G. Contribution of ionically immobilized bovine serum albumin to the retention of enantiomers. J. Chromatogr. 600:37, 1992.