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)...

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Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2021-05, Vol.85 (6), p.1383-1389
Main Authors: Maeda, Satoshi, Mohri, Tomoyo, Inoue, Tsubasa, Asano, Yoshio, Otoki, Yurika, Enomoto, Masaru, Nakagawa, Kiyotaka, Kuwahara, Shigefumi, Ogura, Yusuke
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Language:English
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Summary: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. Graphical Abstract Graphical Abstract Synthesis of a plasmenylethanolamine-[16:0/18:1 n-9].
ISSN:1347-6947
1347-6947
DOI:10.1093/bbb/zbab037