Properties of unusual phospholipids IV: Chemoenzymatic synthesis of phospholipids bearing acetylenic fatty acids

Article abstract of DOI:10.1016/S0040-4020(97)01043-0

14-Octadecynoic (1) and 4-octadecynoic (2) acid were synthesized in high yields (56% and 57%) and incorporated into glycerophosphatidylcholine at sn1- and sn2-position. The head group of these phosphatidylcholines was exchanged using phospholipase D (PLD) in a biphasic system. PLD from Streptomyces antibioticus, Streptomyces sp., peanut and cabbage were studied in this transphosphatidylation reaction. Under optimized conditions (40°C, organic solvent:buffer ratio 1:1.5 (v/v), pH 5.6), the conversion of phosphatidylcholine to the corresponding phospholipids with the head groups glycerol, ethanolamine and L-serine reached 99% at 40°C in 1 h. The quantitative analysis of the transphosphatidylation reactions was performed by TLC-FID.