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. 1977 May;130(2):620–628. doi: 10.1128/jb.130.2.620-628.1977

Phenethyl alcohol inhibition of sn-glycerol 3-phosphate acylation in Escherichia coli.

W D Nunn, P J Cheng, R Deutsch, C T Tang, B E Tropp
PMCID: PMC235260  PMID: 95658

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.

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Selected References

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  1. BLIGH E. G., DYER W. J. A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959 Aug;37(8):911–917. doi: 10.1139/o59-099. [DOI] [PubMed] [Google Scholar]
  2. Barbu E., Polonovski J., Rampini C., Lux M. Modifications de la constitution en phospholipides des cellules d'E. coli cultivées en présence de phenyléthanol. C R Acad Sci Hebd Seances Acad Sci D. 1970 May 25;270(21):2596–2599. [PubMed] [Google Scholar]
  3. Bell R. M. Mutants of Escherichia coli defective in membrane phospholipid synthesis: macromolecular synthesis in an sn-glycerol 3-phosphate acyltransferase Km mutant. J Bacteriol. 1974 Mar;117(3):1065–1076. doi: 10.1128/jb.117.3.1065-1076.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Carter J. R., Jr Cytidine triphosphate: phosphatidic acid cytidyltransferase in Escherichia coli. J Lipid Res. 1968 Nov;9(6):748–754. [PubMed] [Google Scholar]
  5. Cashel M., Lazzarini R. A., Kalbacher B. An improved method for thin-layer chromatography of nucleotide mixtures containing 32P-labelled orthophosphate. J Chromatogr. 1969 Mar 11;40(1):103–109. doi: 10.1016/s0021-9673(01)96624-5. [DOI] [PubMed] [Google Scholar]
  6. Cronan J. E., Jr, Batchelor J. G. An efficient biosynthetic method to prepare fatty acyl chains highly enriched with 13C. Chem Phys Lipids. 1973 Oct;11(3):196–202. doi: 10.1016/0009-3084(73)90019-4. [DOI] [PubMed] [Google Scholar]
  7. Cronan J. E., Jr, Bell R. M. Mutants of Escherichia coli defective in membrane phospholipid synthesis: mapping of sn-glycerol 3-phosphate acyltransferase Km mutants. J Bacteriol. 1974 Oct;120(1):227–233. doi: 10.1128/jb.120.1.227-233.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Cronan J. E., Jr, Bell R. M. Mutants of Escherichia coli defective in membrane phospholipid synthesis: mapping of the structural gene for L-glycerol 3-phosphate dehydrogenase. J Bacteriol. 1974 May;118(2):598–605. doi: 10.1128/jb.118.2.598-605.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Cronan J. E., Jr, Ray T. K., Vagelos P. R. Selection and characterization of an E. coli mutant defective in membrane lipid biosynthesis. Proc Natl Acad Sci U S A. 1970 Mar;65(3):737–744. doi: 10.1073/pnas.65.3.737. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Cronan J. E., Jr Thermal regulation of the membrane lipid composition of Escherichia coli. Evidence for the direct control of fatty acid synthesis. J Biol Chem. 1975 Sep 10;250(17):7074–7077. [PubMed] [Google Scholar]
  11. DAVIS B. D., MINGIOLI E. S. Mutants of Escherichia coli requiring methionine or vitamin B12. J Bacteriol. 1950 Jul;60(1):17–28. doi: 10.1128/jb.60.1.17-28.1950. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Gelmann E. P., Cronan J. E., Jr Mutant of Escherichia coli deficient in the synthesis of cis-vaccenic acid. J Bacteriol. 1972 Oct;112(1):381–387. doi: 10.1128/jb.112.1.381-387.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Glaser M., Nulty W., Vagelos P. R. Role of adenylate kinase in the regulation of macromolecular biosynthesis in a putative mutant of Escherichia coli defective in membrane phospholipid biosynthesis. J Bacteriol. 1975 Jul;123(1):128–136. doi: 10.1128/jb.123.1.128-136.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. HAYASHI S., KOCH J. P., LIN E. C. ACTIVE TRANSPORT OF L-ALPHA-GLYCEROPHOSPHATE IN ESCHERICHIA COLI. J Biol Chem. 1964 Sep;239:3098–3105. [PubMed] [Google Scholar]
  15. KANFER J., KENNEDY E. P. METABOLISM AND FUNCTION OF BACTERIAL LIPIDS. II. BIOSYNTHESIS OF PHOSPHOLIPIDS IN ESCHERICHIA COLI. J Biol Chem. 1964 Jun;239:1720–1726. [PubMed] [Google Scholar]
  16. Klein K., Steinberg R., Fiethen B., Overath P. Fatty acid degradation in Escherichia coli. An inducible system for the uptake of fatty acids and further characterization of old mutants. Eur J Biochem. 1971 Apr;19(3):442–450. doi: 10.1111/j.1432-1033.1971.tb01334.x. [DOI] [PubMed] [Google Scholar]
  17. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  18. Lueking D. R., Goldfine H. The involvement of guanosine 5-diphosphate-3-diphosphate in the regulation of phospholipid biosynthesis in Escherichia coli. Lack of ppGpp inhibition of acyltransfer from acyl-ACP to sn-glycerol 3-phosphate. J Biol Chem. 1975 Jul 10;250(13):4911–4917. [PubMed] [Google Scholar]
  19. MUNKRES K. D., RICHARDS F. M. THE PURIFICATION AND PROPERTIES OF NEUROSPORA MALATE DEHYDROGENASE. Arch Biochem Biophys. 1965 Mar;109:466–479. doi: 10.1016/0003-9861(65)90391-7. [DOI] [PubMed] [Google Scholar]
  20. Nunn W. D., Cronan J. E., Jr Evidence for a direct effect on fatty acid synthesis in rela gene control of membrane phospholipid synthesis. J Mol Biol. 1976 Mar 25;102(1):167–172. doi: 10.1016/0022-2836(76)90080-2. [DOI] [PubMed] [Google Scholar]
  21. Nunn W. D., Cronan J. E., Jr Unsaturated fatty acid synthesis is not required for induction of lactose transport in Escherichia coli. J Biol Chem. 1974 Feb 10;249(3):724–731. [PubMed] [Google Scholar]
  22. Nunn W. D. The inhibition of phospholipid synthesis in escherichia coli by phenethyl alcohol. Biochim Biophys Acta. 1975 Mar 24;380(3):403–413. doi: 10.1016/0005-2760(75)90108-3. [DOI] [PubMed] [Google Scholar]
  23. Nunn W. D., Tropp B. E. Effects of phenethyl alcohol on phospholipid metabolism in Escherichia coli. J Bacteriol. 1972 Jan;109(1):162–168. doi: 10.1128/jb.109.1.162-168.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Pieringer R. A., Bonner H., Jr, Kunnes R. S. Biosynthesis of phosphatidic acid, lysophosphatidic acid, diglyceride, and triglyceride by fatty acyltransferase pathways in Escherichia coli. J Biol Chem. 1967 Jun 10;242(11):2719–2724. [PubMed] [Google Scholar]
  25. Semple K. S., Silbert D. F. Mapping of the fabD locus for fatty acid biosynthesis in Escherichia coli. J Bacteriol. 1975 Mar;121(3):1036–1046. doi: 10.1128/jb.121.3.1036-1046.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. Shopsis C. S., Engel R., Tropp B. E. The inhibition of phosphatidylglycerol synthesis in Escherichia coli by 3,4-dihydroxybutyl-1-phosphonate. J Biol Chem. 1974 Apr 25;249(8):2473–2477. [PubMed] [Google Scholar]
  27. Silbert D. F., Vagelos P. R. Fatty acid mutant of E. coli lacking a beta-hydroxydecanoyl thioester dehydrase. Proc Natl Acad Sci U S A. 1967 Oct;58(4):1579–1586. doi: 10.1073/pnas.58.4.1579. [DOI] [PMC free article] [PubMed] [Google Scholar]
  28. Tang C. T., Engel R., Tropp B. E. L-Glyceraldehude 3-phosphate, a bactericidal agent. Antimicrob Agents Chemother. 1977 Jan;11(1):147–153. doi: 10.1128/aac.11.1.147. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Tunaitis E., Cronan J. E., Jr Characterization of the cardiolipin synthetase activity of Escherichia coli envelopes. Arch Biochem Biophys. 1973 Apr;155(2):420–427. doi: 10.1016/0003-9861(73)90132-x. [DOI] [PubMed] [Google Scholar]
  30. Tyhach R. J., Engel R., Tropp B. E. Metabolic fate of 3,4-dihydroxybutyl-1-phosphonate in Escherichia coli. J Biol Chem. 1976 Nov 10;251(21):6717–6723. [PubMed] [Google Scholar]
  31. VOGEL H. J., BONNER D. M. Acetylornithinase of Escherichia coli: partial purification and some properties. J Biol Chem. 1956 Jan;218(1):97–106. [PubMed] [Google Scholar]

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