Shizuka Manami, Schrader Thomas O, Snapper Marc L
Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, USA.
J Org Chem. 2006 Feb 17;71(4):1330-4. doi: 10.1021/jo0518553.
The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F(2t)-isoprostane and ent-15-epi-F(2t)-isoprostane has allowed for the selective preparation of 15-F(2t)-isoprostanyl phosphatidylethanolamine and ent-15-epi-F(2t)-isoprostanyl phosphatidylcholine. The nature of the headgroups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary 1H NMR and 31P NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.
本文描述了两种异前列腺素磷脂的合成方法。一条新建立的合成15-F(2t)-异前列腺素和对映-15-表-F(2t)-异前列腺素的路线，使得能够选择性地制备15-F(2t)-异前列腺素磷脂酰乙醇胺和对映-15-表-F(2t)-异前列腺素磷脂酰胆碱。头部基团的性质决定了将适当保护的异前列腺素连接到相应溶血磷脂上所采用的偶联策略。初步的1H NMR和31P NMR研究表明，这些异前列腺素磷脂在非极性溶剂中会聚集。
