Synthesis of a plasmenylethanolamine

Satoshi Maeda, Tomoyo Mohri, Tsubasa Inoue, Yoshio Asano, Yurika Otoki, Masaru Enomoto, Kiyotaka Nakagawa, Shigefumi Kuwahara, Yusuke Ogura

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- A nd Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification-oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase high-performance liquid chromatography purification.

    Original languageEnglish
    Pages (from-to)1383-1389
    Number of pages7
    JournalBioscience, Biotechnology and Biochemistry
    Volume85
    Issue number6
    DOIs
    Publication statusPublished - 2021 Jun 1

    Keywords

    • natural product
    • plasmalogen
    • plasmenylethanolamine
    • total synthesis
    • vinyl ether

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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