Synthesis of a plasmenylethanolamine

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

doi:10.1093/bbb/zbab037

Synthesis of a plasmenylethanolamine

Biosci Biotechnol Biochem. 2021 May 25;85(6):1383-1389. doi: 10.1093/bbb/zbab037.

Authors

Satoshi Maeda¹, Tomoyo Mohri², Tsubasa Inoue¹, Yoshio Asano¹, Yurika Otoki¹, Masaru Enomoto², Kiyotaka Nakagawa¹, Shigefumi Kuwahara², Yusuke Ogura^{2

3}

Affiliations

¹ Laboratory of Food and Biodynamic Chemistry, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai, Japan.
² Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai, Japan.
³ Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.

PMID: 33705523
DOI: 10.1093/bbb/zbab037

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- and 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.

Keywords: natural product; plasmalogen; plasmenylethanolamine; total synthesis; vinyl ether.

MeSH terms

Chemistry Techniques, Synthetic
Esterification
Oxidation-Reduction
Plasmalogens / chemical synthesis*
Plasmalogens / chemistry
Stereoisomerism

Substances

Plasmalogens
phosphatidal ethanolamines