eCite Digital Repository

Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: Enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs

Citation

Ghanem, A and Al-Humaidi, E, Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: Enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs, Chirality, 19, (6) pp. 477-484. ISSN 0899-0042 (2007) [Refereed Article]


Preview
PDF
Not available
192Kb
  

Copyright Statement

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

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

DOI: doi:10.1002/chir.20398

Abstract

The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK® IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalidomide was conducted using different nonstandard solvents as eluent and diluent, respectively in high-performance liquid chromatography (HPLC). The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, 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 amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase on silica (Chiralpak IA) on the chiral recognition ability was noted as the bonded phase (Chiralpak IA) was superior in chiral recognition and possesses a higher resolving power in most of the reported cases than the coated one (Chiralpak AD). A few racemates were not or poorly resolved on the immobilized Chiralpak IA or the coated Chiralpak AD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IA upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, methyl-tert-butyl ether, and others when used as eluents or as a dissolving agent for the analyte itself. The direct analysis of a real sample extracted from plasma using DCM on Chiralpak IA is also shown.

Item Details

Item Type:Refereed Article
Keywords:amylose tris(3,5-dimethylphenylcarbamate) • CHIRALPAK IA® • 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:58299
Year Published:2007
Web of Science® Times Cited:9
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-09-25
Last Modified:2009-09-25
Downloads:0

Repository Staff Only: item control page