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 |
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Pages (from-to) | 1383-1389 |
Number of pages | 7 |
Journal | Bioscience, Biotechnology and Biochemistry |
Volume | 85 |
Issue number | 6 |
DOIs | |
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