Synthesis of cardiolipin analogues using phosphoramidite approach

ORGN 556

Murali K Ukkalam, Moghis U Ahmad, and Imran Ahmad. NeoPharm, Inc, 1850, Lakeside Dr, Waukegan, IL 60085
Cardiolipin, a unique dimeric structure phospholipid (also called diphosphatidylglycerol) was first isolated from beef heart and subsequently found in inner membrane of mitochondria where it is found associated with several proteins involved in oxidative phosphorylation and apoptosis.Our focus is to design numerous cardiolipin analogues with varying fatty acids/alkyl chain with or without unsaturation to regulate mitochondrial functions. A novel synthetic approach was developed to prepare cardiolipin analogues.The process involves treatment of optically pure 1,2-O-diacyl-sn- glycerol with mono and bifunctional phosphitylating reagents followed by coupling with a 2-protected glycerol and removal of protecting groups. The chemistry of these compounds and the scope of phosphoramidites in this area will be discussed.