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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
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Synthesis of a plasmenylethanolamine.
Satoshi Maeda1, Tomoyo Mohri2, Tsubasa Inoue1
1Laboratory of Food and Biodynamic Chemistry, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai, Japan.
Bioscience, Biotechnology, and Biochemistry
|March 11, 2021
Summary
Researchers synthesized antioxidative phospholipids, plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), crucial for cell membranes. This 8-step process achieved a concise synthesis of this vital biomolecule.
Area of Science:
- Organic Chemistry
- Biochemistry
- Lipidomics
Background:
- Plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]) is an important antioxidative phospholipid found in cell membranes.
- Understanding its synthesis is key to studying its biological roles.
Purpose of the Study:
- To achieve a concise synthesis of plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]).
- To develop key chemical transformations for constructing this complex phospholipid.
Main Methods:
- An 8-step synthesis starting from an optically active diol.
- Regio- and Z-selective vinyl ether formation using lithioalkoxy allyl intermediates.
- A one-pot phosphite esterification-oxidation for ethanolamine phosphonate moiety construction.
- Purification via reversed-phase high-performance liquid chromatography.
Main Results:
- Successful synthesis of PlsEtn-[16:0/18:1 n-9] with high fidelity.
- Demonstration of key synthetic steps including vinyl ether formation and phosphonate moiety construction.
- Isolation of the pure synthetic product as a piperidine salt.
Conclusions:
- A practical and efficient synthetic route to PlsEtn-[16:0/18:1 n-9] has been established.
- The synthetic methodology enables further studies on the biological functions of antioxidative phospholipids.
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