title: A high-performance liquid chromatographic method for the enantiomeric analysis of the enzymatically synthesized coenzyme A ester of 2-tetradecylglycidic acid.
abstract: 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.
mesh_terms: D000214:Acyl Coenzyme A / Q000031:analogs & derivatives*; D000818:Animals; D001384:Azetidines; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003066:Coenzyme A Ligases / Q000378:metabolism; D066298:In Vitro Techniques; D008862:Microsomes, Liver / Q000378:metabolism; D010171:Palmitoyl Coenzyme A / Q000031:analogs & derivatives* / Q000032:analysis / Q000096:biosynthesis; D051381:Rats; D011919:Rats, Inbred Strains; D012097:Repressor Proteins; D029701:Saccharomyces cerevisiae Proteins; D013237:Stereoisomerism; D000098859:Long-Chain-Fatty-Acid-CoA Ligase
chemical_list: D000214:Acyl Coenzyme A; D001384:Azetidines; D012097:Repressor Proteins; D029701:Saccharomyces cerevisiae Proteins; D010171:Palmitoyl Coenzyme A; C042420:2-tetradecylglycidyl-coenzyme A; D003066:Coenzyme A Ligases; C090799:FAA2 protein, S cerevisiae; D000098859:Long-Chain-Fatty-Acid-CoA Ligase