Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines |
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| Authors: | Jung Michael E Berliner Judith A Koroniak Lukasz Gugiu B Gabriel Watson Andrew D |
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| Affiliation: | Departments of Chemistry and Biochemistry, Medicine/Cardiology, and Pathology, University of California, Los Angeles, California 90095, USA. jung@chem.ucla.edu |
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| Abstract: | An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E 2- sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles. |
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