The preparation of phospholipids by phospholipase D

The transfer of the phosphatidyl residue from egg phosphatidylcholine to primary alkanols catalyzed by phospholipase D was systematically investigated. It was demonstrated that 1) the chain length of the alkanols is of critical importance, e.g. transphosphatidylation does not occur to alkanols or alkandiols with more than six carbon atoms; 2) double or triple bonds in the acceptor molecule do not influence the transfer reaction; 3) fluorine is tolerated in the acceptor molecule, but the transfer rate decreases with increasing atomic weight from chlorine to iodine. Synthetic phosphatidylcholines with large variations in the apolar part of the molecule, the phosphorylcholines of 1.2-diacyl-sn-glycerol, Acyl-propandiol-(1.3) and 1.2-cyclopentadecylmethylidene-glycerol, have been successfully used in the transfer reaction. Transesterification is an attractive route for the synthesis of phospholipids differing in the polar part of the molecule.