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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