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

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

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	1383-1389
Number of pages	7
Journal	Bioscience, Biotechnology and Biochemistry
Volume	85
Issue number	6
DOIs	https://doi.org/10.1093/bbb/zbab037
Publication status	Published - 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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10.1093/bbb/zbab037

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title = "Synthesis of a plasmenylethanolamine",

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. ",

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

note = "Publisher Copyright: {\textcopyright} 2021 The Author(s). Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry.",

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doi = "10.1093/bbb/zbab037",

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AU - Maeda, Satoshi

AU - Mohri, Tomoyo

AU - Inoue, Tsubasa

AU - Asano, Yoshio

AU - Otoki, Yurika

AU - Enomoto, Masaru

AU - Nakagawa, Kiyotaka

AU - Kuwahara, Shigefumi

AU - Ogura, Yusuke

PY - 2021/6/1

Y1 - 2021/6/1

N2 - 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.

AB - 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.

KW - natural product

KW - plasmalogen

KW - plasmenylethanolamine

KW - total synthesis

KW - vinyl ether

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Synthesis of a plasmenylethanolamine

Abstract

Keywords

ASJC Scopus subject areas

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