Chiral Separation, Determination of Absolute Configuration, and High-performance Liquid Chromatography Detection of Enantiomeric 3-hydroxyhexadecanoyl-CoA

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  • Tsuchida Shirou
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Kawamoto Koutarou
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Nunome Kana
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Hamaue Naoya
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Hui Shu-Ping
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Murai Tsuyoshi
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Aoki Takashi
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido
  • Kurosawa Takao
    School of Pharmaceutical Sciences, Health Sciences University of Hokkaido

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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 high-performance 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.

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