Abstract
A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy 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-phenylalanine-methyl ester (IAP) derivatives. The PAP and IAP 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.
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