Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines.

Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines.
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DOI:
10.1021/ol8014804
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发表时间:
2008-10-02
期刊:
影响因子:
5.2
通讯作者:
Watson AD
Watson AD
中科院分区:
化学1区
文献类型:
--
作者:
Jung ME;Berliner JA;Koroniak L;Gugiu BG;Watson AD

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An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E2-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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