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 10(3).
Martin
S F
SF
Department of Chemistry and Biochemistry, University of Texas at Austin 78712, USA.
Hergenrother
P J
PJ
D001409:Bacillus cereus / Q000201:enzymology*; D007700:Kinetics; D008956:Models, Chemical; D016297:Mutagenesis, Site-Directed; D010713:Phosphatidylcholines / Q000138:chemical synthesis* / Q000378:metabolism; D010739:Phospholipase D / Q000378:metabolism; D010738:Type C Phospholipases / Q000235:genetics / Q000378:metabolism*
D010713:Phosphatidylcholines; D010738:Type C Phospholipases; D010739:Phospholipase D