Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses

Ashraf Ghanem, Mohammed Aboul-Enein, Aida Azzouny, Mohammed El-Behairy

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32 Citations (Scopus)

Abstract

The enantioselective resolution of a set of racemic acidic compounds such as non-steroidal anti-inflammatory drugs (NSAIDs) of the group arylpropionic acid derivatives is demonstrated. Thus, a set of lipases were screened and manipulated in either the esterification or hydrolysis mode for the enantioselective kinetic resolution of these racemates in non-standard organic solvents. The accurate determination of the enantiomeric excesses of both substrate and product during such reaction is demonstrated. This was based on the development of a direct and reliable enantioselective high performance liquid chromatography (HPLC) procedure for the simultaneous baseline separation of both substrate and product in one run without derivatization. This was achieved using the immobilized chiral stationary phase namely Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD) which proved to be versatile for the monitoring of the lipase-catalyzed kinetic resolution of racemates in non-standard organic solvents
Original languageEnglish
Pages (from-to)1063-1074
Number of pages12
JournalJournal of Chromatography A
Volume1217
Issue number7
DOIs
Publication statusPublished - 2010

Fingerprint

Liquid chromatography
Lipase
Liquid Chromatography
Organic solvents
Derivatives
Kinetics
Monitoring
Esterification
High performance liquid chromatography
Substrates
Cellulose
Pharmaceutical Preparations
Hydrolysis
Anti-Inflammatory Agents
High Pressure Liquid Chromatography
Acids
cellulose tris-3,5-dimethylphenyl-carbamate
3,5-dimethylphenylcarbamate
cellulose 3,5-dimethylphenylcarbamate

Cite this

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title = "Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses",
abstract = "The enantioselective resolution of a set of racemic acidic compounds such as non-steroidal anti-inflammatory drugs (NSAIDs) of the group arylpropionic acid derivatives is demonstrated. Thus, a set of lipases were screened and manipulated in either the esterification or hydrolysis mode for the enantioselective kinetic resolution of these racemates in non-standard organic solvents. The accurate determination of the enantiomeric excesses of both substrate and product during such reaction is demonstrated. This was based on the development of a direct and reliable enantioselective high performance liquid chromatography (HPLC) procedure for the simultaneous baseline separation of both substrate and product in one run without derivatization. This was achieved using the immobilized chiral stationary phase namely Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD) which proved to be versatile for the monitoring of the lipase-catalyzed kinetic resolution of racemates in non-standard organic solvents",
author = "Ashraf Ghanem and Mohammed Aboul-Enein and Aida Azzouny and Mohammed El-Behairy",
year = "2010",
doi = "10.1016/j.chroma.2009.10.080",
language = "English",
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pages = "1063--1074",
journal = "Journal of Chromatography",
issn = "0021-9673",
publisher = "Elsevier",
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TY - JOUR

T1 - Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses

AU - Ghanem, Ashraf

AU - Aboul-Enein, Mohammed

AU - Azzouny, Aida

AU - El-Behairy, Mohammed

PY - 2010

Y1 - 2010

N2 - The enantioselective resolution of a set of racemic acidic compounds such as non-steroidal anti-inflammatory drugs (NSAIDs) of the group arylpropionic acid derivatives is demonstrated. Thus, a set of lipases were screened and manipulated in either the esterification or hydrolysis mode for the enantioselective kinetic resolution of these racemates in non-standard organic solvents. The accurate determination of the enantiomeric excesses of both substrate and product during such reaction is demonstrated. This was based on the development of a direct and reliable enantioselective high performance liquid chromatography (HPLC) procedure for the simultaneous baseline separation of both substrate and product in one run without derivatization. This was achieved using the immobilized chiral stationary phase namely Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD) which proved to be versatile for the monitoring of the lipase-catalyzed kinetic resolution of racemates in non-standard organic solvents

AB - The enantioselective resolution of a set of racemic acidic compounds such as non-steroidal anti-inflammatory drugs (NSAIDs) of the group arylpropionic acid derivatives is demonstrated. Thus, a set of lipases were screened and manipulated in either the esterification or hydrolysis mode for the enantioselective kinetic resolution of these racemates in non-standard organic solvents. The accurate determination of the enantiomeric excesses of both substrate and product during such reaction is demonstrated. This was based on the development of a direct and reliable enantioselective high performance liquid chromatography (HPLC) procedure for the simultaneous baseline separation of both substrate and product in one run without derivatization. This was achieved using the immobilized chiral stationary phase namely Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD) which proved to be versatile for the monitoring of the lipase-catalyzed kinetic resolution of racemates in non-standard organic solvents

U2 - 10.1016/j.chroma.2009.10.080

DO - 10.1016/j.chroma.2009.10.080

M3 - Article

VL - 1217

SP - 1063

EP - 1074

JO - Journal of Chromatography

JF - Journal of Chromatography

SN - 0021-9673

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ER -