Enzyme-mediated synthesis of two diastereoisomeric forms of phosphatidylglycerol and of diphosphatidylglycerol (cardiolipin)

Abstract

3-sn-Phosphatidyl-1′-sn-glycerol and its stereoisomer 3-sn-phosphatidyl-3′-sn-glycerol are prepared through phospholipase D-catalysed transphosphatidylation of natural phosphatidylcholine with the two enantiomeric (R)- and (S)-isopropylideneglycerols and subsequent hydrolysis of the phospholipids obtained. If glycerol is the alcohol donor in the same reaction, a mixture of stereoisomers is obtained. When the enzyme from savoy cabbage is used, the two compounds are obtained as the only products. With PLD from Streptomyces as catalyst, the initially formed phosphatidylglycerols are quantitatively transformed into diphosphatidylglycerol (cardiolipin).