Comparison, applications, advantages, and limitations of immobilized and coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases in HPLC

Ashraf Ghanem, Hassan Y. Aboul-Enein

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A direct high performance liquid Chromatographic enantioselective separation of a set of racemic acidic drugs on the new immobilized and conventional coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, respectively) was studied using n-hexane and 2-propanaol (80:20 v/v), containing TFA (0.1%) as mobile phase. The separation and elution order of the enantiomers on both columns under the same conditions were compared. 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 coated phase (Chiralpak AD) possesses a higher resolving power than the immobilized one (Chiralpak IA). A few racemates, which were not or poorly resolved on the immobilized Chiralpak IA were most efficiently resolved on the coated Chiralpak AD. However, the immobilized phase withstands the prohibited HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and others when used as eluents or as a dissolving agent for the analyte itself. The versatility of the immobilized Chiralpak IA in monitoring reactions performed in dichloromethane using direct analysis techniques without further purification, workup, or removal of dichloromethane, was studied on a representative example consisting of the lipase-catalyzed enantioselective esterification of flurbiprofen, with n-butanol in dichloromethane as organic solvent.

Original languageEnglish
Pages (from-to)2863-2874
Number of pages12
JournalJournal of Liquid Chromatography and Related Technologies
Volume28
Issue number18
DOIs
Publication statusPublished - 21 Nov 2005

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Methylene Chloride
High Pressure Liquid Chromatography
Flurbiprofen
1-Butanol
Enantiomers
Esterification
Optical resolving power
Lipase
Silicon Dioxide
Immobilization
Organic solvents
Purification
Chiralpak AD
Monitoring
Liquids
Pharmaceutical Preparations

Cite this

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title = "Comparison, applications, advantages, and limitations of immobilized and coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases in HPLC",
abstract = "A direct high performance liquid Chromatographic enantioselective separation of a set of racemic acidic drugs on the new immobilized and conventional coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, respectively) was studied using n-hexane and 2-propanaol (80:20 v/v), containing TFA (0.1{\%}) as mobile phase. The separation and elution order of the enantiomers on both columns under the same conditions were compared. 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 coated phase (Chiralpak AD) possesses a higher resolving power than the immobilized one (Chiralpak IA). A few racemates, which were not or poorly resolved on the immobilized Chiralpak IA were most efficiently resolved on the coated Chiralpak AD. However, the immobilized phase withstands the prohibited HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and others when used as eluents or as a dissolving agent for the analyte itself. The versatility of the immobilized Chiralpak IA in monitoring reactions performed in dichloromethane using direct analysis techniques without further purification, workup, or removal of dichloromethane, was studied on a representative example consisting of the lipase-catalyzed enantioselective esterification of flurbiprofen, with n-butanol in dichloromethane as organic solvent.",
keywords = "Acidic drugs, Amylose tris-(3,5-dimethylphenylcarbamate), Chiralpak AD, Chiralpak IA, Enantioseparation, HPLC, Kinetic resolution",
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T1 - Comparison, applications, advantages, and limitations of immobilized and coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases in HPLC

AU - Ghanem, Ashraf

AU - Aboul-Enein, Hassan Y.

PY - 2005/11/21

Y1 - 2005/11/21

N2 - A direct high performance liquid Chromatographic enantioselective separation of a set of racemic acidic drugs on the new immobilized and conventional coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, respectively) was studied using n-hexane and 2-propanaol (80:20 v/v), containing TFA (0.1%) as mobile phase. The separation and elution order of the enantiomers on both columns under the same conditions were compared. 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 coated phase (Chiralpak AD) possesses a higher resolving power than the immobilized one (Chiralpak IA). A few racemates, which were not or poorly resolved on the immobilized Chiralpak IA were most efficiently resolved on the coated Chiralpak AD. However, the immobilized phase withstands the prohibited HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and others when used as eluents or as a dissolving agent for the analyte itself. The versatility of the immobilized Chiralpak IA in monitoring reactions performed in dichloromethane using direct analysis techniques without further purification, workup, or removal of dichloromethane, was studied on a representative example consisting of the lipase-catalyzed enantioselective esterification of flurbiprofen, with n-butanol in dichloromethane as organic solvent.

AB - A direct high performance liquid Chromatographic enantioselective separation of a set of racemic acidic drugs on the new immobilized and conventional coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, respectively) was studied using n-hexane and 2-propanaol (80:20 v/v), containing TFA (0.1%) as mobile phase. The separation and elution order of the enantiomers on both columns under the same conditions were compared. 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 coated phase (Chiralpak AD) possesses a higher resolving power than the immobilized one (Chiralpak IA). A few racemates, which were not or poorly resolved on the immobilized Chiralpak IA were most efficiently resolved on the coated Chiralpak AD. However, the immobilized phase withstands the prohibited HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and others when used as eluents or as a dissolving agent for the analyte itself. The versatility of the immobilized Chiralpak IA in monitoring reactions performed in dichloromethane using direct analysis techniques without further purification, workup, or removal of dichloromethane, was studied on a representative example consisting of the lipase-catalyzed enantioselective esterification of flurbiprofen, with n-butanol in dichloromethane as organic solvent.

KW - Acidic drugs

KW - Amylose tris-(3,5-dimethylphenylcarbamate)

KW - Chiralpak AD

KW - Chiralpak IA

KW - Enantioseparation

KW - HPLC

KW - Kinetic resolution

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U2 - 10.1080/10826070500222934

DO - 10.1080/10826070500222934

M3 - Article

VL - 28

SP - 2863

EP - 2874

JO - Journal of Liquid Chromatography Related Technologies

JF - Journal of Liquid Chromatography Related Technologies

SN - 1082-6076

IS - 18

ER -