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Synthesis 2024; 56(11): 1787-1792
DOI: 10.1055/a-2257-0684
paper

A Convenient Method for Synthesizing 1-Alkyl-2-acyl-sn-glycero-3-phosphoethanolamines

Tatsuo Okauchi  ∗
,
Kouta Tsubaki
,
Yuri Higuma
,
Hirokazu Shimooka
,
Mitsuru Kitamura
We gratefully acknowledge financial support for this research from the Institute of Rheological Functions of Food.
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Dedicated to Professor Koichi Narasaka in celebration of his 80th birthday (Sanju)

Abstract

A convenient method for synthesizing 1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamines (1-alkyl-2-acyl-GPEs) starting from an optical active alcohol is described. In this method, the phosphate group was introduced through the transesterification that we developed, and a protected 1-alkyl-2-lyso-GPE was employed as an intermediate. This compound is stable and serves as a common intermediate for the synthesis of various 1-alkyl-2-acyl-GPEs with different acyl groups.

Key words

ether phospholipids - glycerophospholipids - phosphoethanolamines - transesterification - phosphorylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2257-0684.
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Publication History

Received: 26 December 2023

Accepted after revision: 30 January 2024

Accepted Manuscript online:
30 January 2024

Article published online:
20 February 2024

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