Chiral separation, determination of absolute configuration, and high-performance liquid chromatography detection of enantiomeric 3-hydroxyhexadecanoyl-CoA

Abstract

The enoyl-coenzyme A (CoA) hydratase catalyzes the hydration of 2-enoyl-CoA to yield 3-hydroxyacyl-CoA in mitochondrial and peroxisomal β-oxidation. However, the stereospecificities of these hydratases differ from each other. To provide clear evidence of the stereospecificities of hydratases, the absolute configuration of 3-hydroxyhexadecanoyl-CoAs was determined, and they were subjected to a highperformance liquid chromatography (HPLC) using a chiral separation column. The retention time of 3(R)- hydroxyhexadecanoyl-CoA was shorter than that of 3(S)-hydroxyhexadecanoyl-CoA. The HPLC analysis carried out using a chiral separation column is considered to be useful for the study of enoyl-CoA hydratase. Copyright ©2011 by Japan Oil Chemists' Society.