title: Phenethyl alcohol inhibition of sn-glycerol 3-phosphate acylation in Escherichia coli.
abstract: In vivo and in vitro experiments were performed to determine how phenethyl alcohol (PEA) inhibits phospholipid synthesis in Escherichia coli. This drug drastically reduced the rate of incorporation of sn-glycerol 3-phosphate into the phospholipids of an sn-glycerol 3-phosphate auxotroph. PEA also reduced the rate of fatty acid incorporation into the phospholipids of a fatty acid auxotroph. The kinetics of PEA inhibition of the rate of incorporation of sn-glycerol 3-phosphate were almost identical to those of PEA inhibition of the rate of fatty acid incorporation into phospholipids. The in vivo experiments suggested that the rate-limiting step(s) in phospholipid biosynthesis inhibited by PEA is at the level of the acylation of sn-glycerol 3-phosphate or beyond this step. PEA inhibited the sn-glycerol 3-phosphate acyltransferase with either palmitoyl coenzyme A or palmitoyl-acyl carrier protein as the acyl donor. This drug, however, had no effect on the cytidine 5'-diphosphate-diglyceride:glycerol 3-phosphate phosphatidyl transferase, cytidine 5'-diphosphate-diglyceride:L-serine phosphatidyl transferase, and acyl coenzyme A:lysophatidic acid acyltransferase. The in vitro findings suggested that PEA inhibits phospholipid synthesis primarily at the level of sn-glycerol 3-phosphate acyltransferase.
mesh_terms: D000215:Acylation; D004926:Escherichia coli / Q000187:drug effects / Q000378:metabolism*; D000431:Ethanol / Q000031:analogs & derivatives*; D005227:Fatty Acids / Q000378:metabolism; D005992:Glycerol-3-Phosphate O-Acyltransferase / Q000032:analysis; D005994:Glycerophosphates / Q000378:metabolism*; D007700:Kinetics; D010626:Phenylethyl Alcohol / Q000494:pharmacology*; D010743:Phospholipids / Q000096:biosynthesis; D012265:Ribonucleotides / Q000032:analysis
chemical_list: D005227:Fatty Acids; D005994:Glycerophosphates; D010743:Phospholipids; D012265:Ribonucleotides; D000431:Ethanol; C029620:alpha-glycerophosphoric acid; D005992:Glycerol-3-Phosphate O-Acyltransferase; D010626:Phenylethyl Alcohol