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Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates

Citation

Ghanem, A, Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates, Journal of Separation Science, 30, (7) pp. 1019 - 1028. ISSN 1615-9306 (2007) [Refereed Article]


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The definitive published version is available online at: http://interscience.wiley.com

Official URL: http://interscience.wiley.com

DOI: doi:10.1002/jssc.200600357

Abstract

Chiralpak IB, a new chiral stationary phase (CSP) containing cellulose tris(3,5-dimethylphenylcarabamate) immobilized onto silica gel, is investigated for the direct enantioselective separation of a set of racemic N-alkylated barbiturates and analogs of thalidomide alkylated in position 3 of the piperidin-2,6-dione ring using different nonstandard solvents such as dichloromethane (DCM), ethyl acetate, THF, methyl tert-butyl ether as an eluent and diluent, respectively, in HPLC. The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated cellulose tris(3,5-dimethylphenylcarbamate) CSPs (Chiralpak IB and Chiralcel OD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the cellulose tris-(3,5-dimethylphenylcarbamate) CSP on silica (Chiralpak IB) on the chiral recognition ability was noted as the coated phase (Chiralcel OD) possesses a higher resolving power in some cases than the immobilized one (Chiralpak IB). However, a few racemates, which were not or poorly resolved on the immobilized Chiralpak IB or the coated Chiralcel OD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IB upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents mentioned previously when used as eluents or as a dissolving agent for the analyte itself. An example of inversion or apparent inversion of elution order on Chiralpak IB is reported. The direct analysis of a spiked plasma sample extracted using DCM on Chiralpak IB is also shown.

Item Details

Item Type:Refereed Article
Keywords:Cellulose tris(3,5-dimethylphenylcarbamate) Chiralcel OD Chiralpak IB Elution order Enantioseparation HPLC N-Alkylated barbiturates Thalidomide analogs
Research Division:Chemical Sciences
Research Group:Analytical Chemistry
Research Field:Separation Science
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:58324
Year Published:2007
Web of Science® Times Cited:18
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-09-25
Last Modified:2009-09-25
Downloads:0

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