Volume 8, Issue 6 pp. 446-451

Full Paper

HPLC enantioseparation on cellulose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase: Influences of pore size of silica gel, coating amount, coating solvent, and column temperature on chiral discrimination

Eiji Yashima,

Eiji Yashima

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

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Pennapa Sahavattanapong,

Pennapa Sahavattanapong

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

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Yoshio Okamoto,

Corresponding Author

Yoshio Okamoto

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, 464-01, JapanSearch for more papers by this author

Eiji Yashima,

Eiji Yashima

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

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Pennapa Sahavattanapong,

Pennapa Sahavattanapong

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

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Yoshio Okamoto,

Corresponding Author

Yoshio Okamoto

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan

Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya, 464-01, JapanSearch for more papers by this author

First published: 1996

https://doi.org/10.1002/(SICI)1520-636X(1996)8:6<446::AID-CHIR6>3.0.CO;2-A

Citations: 52

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Abstract

Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) was coated on large-pore silica gels and used as a chiral stationary phase (CSP) for high-performance liquid chromatographic separation of enantiomers. The influences of pore size of silica gel, coating amount of CDMPC, coating solvent, and column temperature on chiral discrimination were investigated. CSPs prepared with a large-pore silica gel having a small surface area showed higher chiral recognition. The amount of CDMPC adsorbed on the silica gel influenced the chiral recognition of some racemates. Loading capacity of racemates increased with an increase of the amount of CDMPC supported on the silica gel, and a CSP coated with 45% CDMPC by weight can be used for both analytical and semi-preparative scale separations. The CDMPC, coated using acetone as the coating solvent, exhibited, in many cases, higher enantioselectivity than that obtained with tetrahydrofuran F as the coating solvent. © 1996 Wiley-Liss, Inc.

Literature Cited

1 Waldeck, B. Biological significance of the enantiomeric purity of drugs. Chirality 5: 350–355, 1993.
10.1002/chir.530050514
CAS PubMed Web of Science® Google Scholar
2 Millership, J.S., Fitzpatrick, A. Commonly used chiral drugs: A survey. Chirality 5: 573–576, 1993.
10.1002/chir.530050802
CAS PubMed Web of Science® Google Scholar
3 Taylor, D.R., Maher, K. Chiral separations by high-performance liquid chromatography. J. Chromatogr. Sci. 30: 67–85, 1992.
10.1093/chromsci/30.3.67
CAS Web of Science® Google Scholar
4 Okamoto, Y. Separation optical isomers by chiral HPLC. Chemtech: 176–181, 1987.
Google Scholar
5 Allenmark, S.G. Chromatographic Enantioseparation: Methods and Applications. Chichester: Ellis Horwood, 1988.
Google Scholar
6 Dingenen, J. In: A practical approach to chiral separations by liquid chromatography. G. Subramanian, ed. Chapter 6, New York: VCH Publishers, 1994.
Google Scholar
7 Drayer, D.E. Pharmacodynamic and pharmacokinetic differences between drug enantiomers in humans: An overview. Clin. Pharmacol. Ther. 40: 125–133, 1986.
10.1038/clpt.1986.150
CAS PubMed Web of Science® Google Scholar
8 Okamoto, Y., Kaida, Y. Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases. J. Chromatogr. A 666: 403–419, 1994.
10.1016/0021-9673(94)80400-1
CAS Web of Science® Google Scholar
9 Pirkle, W.H., Pochapsky, T.C. Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers. Chem. Rev. 89: 347–362, 1989.
10.1021/cr00092a006
CAS Web of Science® Google Scholar
10 Blaschke, G. Chromatographic resolution of chiral drugs on polyamides and cellulose triacetate. J. Liquid Chromatogr. 9: 341–368, 1986.
10.1080/01483918608076641
CAS Web of Science® Google Scholar
11 Okamoto, Y., Kawashima, M., Hatada, K. Controlled chiral recognition of cellulose trisphenylcarbamate derivatives supported on silica gel. J. Chromatogr. 363: 173–186, 1986.
10.1016/S0021-9673(01)83736-5
CAS Web of Science® Google Scholar
12 Okamoto, Y., Cao, A., Aburatani, R., Hatada, K. Optical resolution of alcohols as carbamates by HPLC on cellulose tris(phenylcarbamate) derivatives. Bull. Chem. Soc. Jpn. 60: 3999–4003, 1987.
10.1246/bcsj.60.3999
CAS Web of Science® Google Scholar
13 Ikeda, K., Hamasaki, T., Kohno, H., Ogawa, T., Matsumoto, T., Sakai, J. Direct separation of enantiomers by reversed-phase high performance liquid chromatography on cellulose tris(3,5-dimethylphenylcarbamate). Chem. Lett. 1089–1090, 1989.
Google Scholar
14 Ishikawa, A., Shibata, T. Cellulosic chiral stationary phase under reversedphase condition. J. Liquid Chromatogr. 16: 859–878, 1993.
10.1080/10826079308020939
CAS Web of Science® Google Scholar
15 Felix, G., Zhang, T. Chiral packing materials for high-performance liquid chromatographic resolution of enantiomers based on substituted branched polysaccharides coated on silica gel. J. Chromatogr. A 639: 141–149, 1993.
10.1016/0021-9673(93)80248-7
CAS PubMed Web of Science® Google Scholar
16 Grieb, S.J., Matlin, S.A., Phillips, J.G., Belenguer, A.M., Ritchie, H.J. Chiral HPLC with carbohydrate carbamates: Influence of support structure on enantioselectivity. Chirality 6: 129–134, 1994.
10.1002/chir.530060213
CAS Web of Science® Google Scholar
17 Grieb, S.J., Matlin, S.A., Belenguer, A.M., Ritchie, H.J. Chiral high-performance liquid chromatography with cellulose carbamate-coated phases. J. Chromatogr. A 697: 271–278, 1994.
10.1016/0021-9673(94)00868-A
Web of Science® Google Scholar
18 Vogt, U., Zugenmaier, P. Structural models for some liquid crystalline cellulose derivatives. Ber. Bunsenges. Phys. Chem. 89: 1217–1224, 1985.
10.1002/bbpc.19850891120
CAS Web of Science® Google Scholar
19 Shibata, T., Sei, T., Nishimura, H. Hysteretic effect of the coating solvent on chiral recognition by cellulose derivative. Chromatographia 24: 552–554, 1987.
10.1007/BF02688543
CAS Web of Science® Google Scholar
20 Okamoto, Y., Honda, S., Hatada, K., Yuki, H. Chromatographic resolution IX. High-performance liquid chromatographic resolution of enantiomers on optically active poly(triphenylmethyl methacrylate). J. Chromatogr. 350: 127–134, 1985.
10.1016/S0021-9673(01)93512-5
CAS Web of Science® Google Scholar

Citing Literature

Volume8, Issue6

1996

Pages 446-451

HPLC enantioseparation on cellulose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase: Influences of pore size of silica gel, coating amount, coating solvent, and column temperature on chiral discrimination

Abstract

Literature Cited

Citing Literature

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HPLC enantioseparation on cellulose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase: Influences of pore size of silica gel, coating amount, coating solvent, and column temperature on chiral discrimination

Abstract

Literature Cited

Citing Literature

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