Synthesis of isoprostanyl phosphatidylcholine and isoprostanyl phosphatidylethanolamine.
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.
Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, USA.
Manami
M
Shizuka
Thomas O
TO
Schrader
Marc L
ML
Snapper
D028441:F2-Isoprostanes / Q000138:chemical synthesis; D028421:Isoprostanes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis*; D012997:Solvents / Q000494:pharmacology
D028441:F2-Isoprostanes; D028421:Isoprostanes; D008823:Micelles; D010713:Phosphatidylcholines; D010714:Phosphatidylethanolamines; D012997:Solvents; C483858:phosphatidylethanolamine