Skip to main content
Log in

Inhibition ofd-alanyl-d-alanine ligase in different bacterial species by amino phosphonic acids

  • Published:
Current Microbiology Aims and scope Submit manuscript

Abstract

A comparative study was performed on the kinetic properties and the specificity ofd-alanyl-d-alanine ligases fromPseudomonas aeruginosa, Streptococcus faecalis, andStaphylococcus aureus, using some aminophosphonic acids and related compounds.dl-I-Aminoethylphosphonic acid was shown to be a competitive inhibitor of theP. aeruginosa andS. faecalis ligases; assuming ad-form stereospecificity, its activity was nearly equal to that ofd-cycloserine. 2-Aminoethylphosphonate was found to be a weak inhibitor of the ligases, in contrast to the carboxylic analog, β-alanine. γ-Aminobutyric acid and phosphoethanolamine also exhibited some inhibitory properties.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. Adams, E., Mukherjee, K. L., Dunathan, H. C. 1974. Alanine racemase ofPseudomonas. Observations on substrate and inhibitor specificity. Archives of Biochemistry and Biophysics165:126–132.

    Article  PubMed  CAS  Google Scholar 

  2. Allen, J. G., Atherton, F. R., Hall, M. J., Hassal, C. H., Holmes, S. W., Lambert, R. W., Nisbet, L. J., Ringrose, P. S. 1978. Phosphonopeptides, a new class of synthetic antibacterial agents. Nature272:56–58.

    Article  PubMed  CAS  Google Scholar 

  3. Garrigou-Lagrange, C. 1978. Analyse des spectres de vibration de la β-alanine, de la taurine et de la ciliatine β. Canadian Journal of Chemistry.56:663–669.

    Article  CAS  Google Scholar 

  4. Ito, E., Strominger, J. L. 1962. Enzymatic synthesis of the peptide in bacterial uridine nucleotides. I. Enzymatic addition ofl-alanine,d-glutamic acid andl-lysine. The Journal of Biological Chemistry237:2689–2695.

    CAS  Google Scholar 

  5. Ito, E., Strominger, J. L. 1962. Enzymatic synthesis of the peptide in bacterial uridine nucleotides. II. Enzymatic synthesis and addition ofd-alanyl-d-alanine. The Journal of Biological Chemistry237:2696–2703.

    CAS  Google Scholar 

  6. Lacoste, A. M., Cassaigne, A., Neuzil, E. 1975. Acides aminés phosphoniques et croissance dePseudomonas aeruginosa. Comptes Rendus de l'Académie des Sciences, Paris, Series D280:1173–1176.

    CAS  Google Scholar 

  7. Lacoste, A. M., Poulsen, M., Cassaigne, A., Neuzil, E. 1976. Recherches sur l'action antibiotique de l'acidedl-I-amino-éthylphosphonique. Journées Biochimiques Franco-Belges 24–26 Juin 1976. Résumés p. 46.

  8. Lambert, M. P., Neuhaus, F. C. 1972. Mechanism ofd-cycloserine action: Alanine racemase fromEscherichia coli Wl. Journal of Bacteriology110:978–987.

    PubMed  CAS  Google Scholar 

  9. Lowry, O. H., Rosebrough, N. J., Farr, A. L., Randall, R. J. 1951. Protein measurement with the Folin phenol reagent. The Journal of Biological Chemistry193:265–275.

    PubMed  CAS  Google Scholar 

  10. Lugtenberg, E. J. J. 1972. Studies onEscherichia coli enzymes involved in the synthesis of uridine diphosphate-N-acetylmuramyl-penta-peptide. Journal of Bacteriology110:26–34.

    PubMed  CAS  Google Scholar 

  11. Neuhaus, F. C. 1962. The enzymatic synthesis ofd-alanyl-d-alanine. I. Purification and properties ofd-alanyl-d-alanine synthetase. The Journal of Biological Chemistry237:778–786.

    PubMed  CAS  Google Scholar 

  12. Neuhaus, F. C. 1962. The enzymatic synthesis ofd-alanyl-d-alanine. II. Kinetic studies ond-alanyl-d-alanine synthetase. The Journal of Biological Chemistry237:3128–3135.

    PubMed  CAS  Google Scholar 

  13. Neuhaus, F. C., Carpenter, C. V., Miller, J. L., Lee, N. M., Gragg, M., Stickgold, R. A. 1969. Enzymatic synthesis ofd-alanyl-d-alanine. Control ofd-alanine:d-alanine ligase (ADP). Biochemistry8:5119–5124.

    Article  PubMed  CAS  Google Scholar 

  14. Neuhaus, F. C., Lynch, J. L. 1962. Studies on the inhibition ofd-alanyl-d-alanine synthetase by the antibioticd-cycloserine. Biochemical and Biophysical Research Communications8:377–382.

    Article  PubMed  CAS  Google Scholar 

  15. Neuhaus, F. C., Lynch, J. L. 1964. The enzymatic synthesis ofd-alanyl-d-alanine. III. On the inhibition ofd-alanyl-d-alanine synthetase by the antibioticd-cycloserine. Biochemistry3:471–480.

    Article  PubMed  CAS  Google Scholar 

  16. Richard, H., Clin, B. 1974. Etude conformationnelle par résonance magnétique nucléaire du proton d'analogues phosphoniques des têtes polaires des phospholipides. Comptes Rendus de l'Académie des Sciences, Paris, Series C278:1275–1278.

    CAS  Google Scholar 

  17. Steward, E. G., Player, R., Quilliam, J. P., Brown, D. A., Pringle, M. J. 1971. Molecular conformation of GABA. Nature New Biology233:87–88.

    Article  PubMed  CAS  Google Scholar 

  18. Yanai, A., Kato, K., Beppu, T., Arima, K 1976. Peptidoglycan ofPseudomonas aeruginosa. Agricultural and Biological Chemistry40:1505–1508.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lacoste, AM., Poulsen, M., Cassaigne, A. et al. Inhibition ofd-alanyl-d-alanine ligase in different bacterial species by amino phosphonic acids. Current Microbiology 2, 113–117 (1979). https://doi.org/10.1007/BF02603067

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02603067

Keywords

Navigation