A high-performance liquid chromatographic method for the enantiomeric analysis of the enzymatically synthesized coenzyme A ester of 2-tetradecylglycidic acid

✍ Scribed by Larry E. Weaner; David C. Hoerr

• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 620 KB
• Volume: 160
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(87)90053-4

✦ Synopsis

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 chirat 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:Senantiomers (88% ee). The result demonstrates the stereoselectivity ofthe long-chain fatty acid-coenzyme A synthetase for chiral fatty acid epoxide, TDGA. o 1987 Academic Press, Inc.