AI Article Synopsis
- Neuroprotectin D1 / protectin D1 is a powerful lipid mediator that plays a role in anti-inflammatory and neuroprotective processes, synthesized from docosahexaenoic acid.
- The synthesis method is highly controlled and involves key steps such as epoxide opening and cis-reduction to ensure the correct geometry of the compounds.
- This approach also successfully synthesized aspirin-triggered neuroprotectin D1, enabling researchers to confirm the stereochemistry of both synthetic and naturally derived compounds.
Article Abstract
Neuroprotectin D1 / protectin D1, a potent anti-inflammatory, proresolving, and neuroprotective lipid mediator derived biosynthetically from docosahexaenoic acid, was prepared in enantiomerically pure form via total organic synthesis. The synthetic strategy is highly stereocontrolled and convergent, featuring epoxide opening of glycidol starting materials for the introduction of the 10(R) and 17(S) hydroxyl groups. The desired alkene Z geometry was secured via the cis-reduction of alkyne precursors, while the conjugated E,E,Z triene was introduced at the end, in order to minimize Z/E isomerization. The same strategy, was also employed for the total synthesis of aspirin-triggered neuroprotectin D1 / protectin D1 having the 17(R)-stereochemistry. Synthetic compounds obtained with the reported method were matched with endogenously derived materials, and helped establish their complete stereochemistry.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3370686 | PMC |
| http://dx.doi.org/10.1016/j.tetlet.2012.01.032 | DOI Listing |
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