Enzymatic synthesis of a modified phospholipid and its evaluation as a substrate for B. cereus phospholipase C

The novel phospholipid 2, which bears a tert-butyl moiety in place of the natural trimethyl ammonium group of phosphatidylcholine, has been enzymatically synthesized via a transphosphatidylation reaction mediated by phospholipase D. The change from the choline headgroup in 1 to the tert-butyl group in 2 reduced the efficiency of hydrolysis by the phosphatidylcholine-preferring phospholipase C from Bacillus cereus by a factor of greater than 103.