A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids

✍ Scribed by Lian-Ying Zhang; Mats Hamberg

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 737 KB
• Volume: 74
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(94)90056-6

✦ Synopsis

A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenylalaninemethyl ester (IAP) derivatives. The PAP and lAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.