Document Detail


A high-performance liquid chromatographic method for the enantiomeric analysis of the enzymatically synthesized coenzyme A ester of 2-tetradecylglycidic acid.
MedLine Citation:
PMID:  3578758     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The enantiomeric composition of an enzymatically synthesized sample of the coenzyme A ester of 2-tetradecylglycidic acid (TDGA-CoA) was determined by the use of high-performance liquid chromatography with a chiral stationary phase. The stationary phase was commercially available and consisted of (R)-N-(3,5-dinitrobenzoyl)phenylglycine covalently bonded to aminopropyl silica gel. Analysis was performed using the phenacyl derivative of 2-tetradecylglycidic acid (TDGA), obtained by mild hydrolysis of the TDGA-CoA followed by reaction of the extracted TDGA with phenacyl chloride. Chromatography showed the enantiomeric purity of TDGA-CoA, synthesized in a rat liver microsomal enzyme mixture over a 2-h period, to be a 15.6:1 ratio of the R:S enantiomers (88% ee). The result demonstrates the stereoselectivity of the long-chain fatty acid-coenzyme A synthetase for chiral fatty acid epoxide, TDGA.
Authors:
L E Weaner; D C Hoerr
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Publication Detail:
Type:  In Vitro; Journal Article    
Journal Detail:
Title:  Analytical biochemistry     Volume:  160     ISSN:  0003-2697     ISO Abbreviation:  Anal. Biochem.     Publication Date:  1987 Feb 
Date Detail:
Created Date:  1987-05-22     Completed Date:  1987-05-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0370535     Medline TA:  Anal Biochem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  316-22     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Acyl Coenzyme A / analogs & derivatives*
Animals
Azetidines*
Chromatography, High Pressure Liquid / methods*
Coenzyme A Ligases / metabolism
Microsomes, Liver / metabolism
Palmitoyl Coenzyme A / analogs & derivatives*,  analysis,  biosynthesis
Rats
Rats, Inbred Strains
Repressor Proteins*
Saccharomyces cerevisiae Proteins*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Acyl Coenzyme A; 0/Azetidines; 0/Repressor Proteins; 0/Saccharomyces cerevisiae Proteins; 1763-10-6/Palmitoyl Coenzyme A; 92142-38-6/2-tetradecylglycidyl-coenzyme A; EC 6.2.1.-/Coenzyme A Ligases; EC 6.2.1.3/FAA2 protein, S cerevisiae; EC 6.2.1.3/long-chain-fatty-acid-CoA ligase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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