Synthesis of Metal Complex Modified Phospholipids by Phospholipase D-Catalyzed Transphosphatidylation

摘要

The synthesis of ferrocenyl-functionalized phospholipid was achieved through a biphasic transphosphatidylation reaction catalyzed by phospholipase D. Thus, the 1,2-distearoyl-.s?-glycero-3-phosphocholine headgroup was modified with hydroxymethylferrocene. 1,2-distearoyl-s?-glycero-3-rnphosphocholine was chosen because it bears a choline group required for successful phospholipase D-catalysis. The use of hydroxymethylferrocene, as an electroactive tether, was appropriate since the present transphosphatidylation reaction is specific to primary alcohols. Mass spectrometry and phosphorus nuclear magnetic resonance analysis confirmed the formation of the redox active phospholipid and also revealed downstream instabilities that will need to be resolved prior to use in liposome assemblies.