Abstract
ANTIBIOTICS of the group that includes the penicillins, the cephalosporins, D-cycloserine and vancomycin, act by interfering with the biosynthesis of bacterial cell walls1,2. This is achieved by inhibiting the formation, or the subsequent utilisation in cross-linking, of the terminal D-Ala-D-Ala units which occur in the peptide chains of the cell-wall peptidoglycans of all pathogenic bacteria so far investigated3ā5. We have sought new synthetic compounds, related to D-Ala-D-Ala, that have similar antibacterial action. We report here that certain phosphonopeptides, of which L-alanyl-āLā-l-aminoethylphosphonic acid (alaphosphin) is typical, inhibit the growth of various important pathogenic bacteria in vitro and in infected animals.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Ghuysen, J.-M., Strominger, J. L. & Tipper, D. J. in Comprehensive Biochemistry 26A (eds Florkin, M. & Stotz, E. H.) (Elsevier, Amsterdam, 1967).
Strominger, J. L. in The Bacteria (eds Gunsalus, I. C. & Stanier, R. Y.) 3, 413 (Academic, London, 1962).
Ito, E. & Strominger, J. L. J. biol. Chem. 237, 2696ā2703 (1962).
Tipper, D. J. & Strominger, J. L. Proc. natn. Acad. Sci. U.S.A. 54, 1133ā1141 (1965).
Rogers, H. J. & Perkins, H. R. Cell Walls and Membranes 214, 220; 261 (Spon, London, 1968).
Grzonka, Z. & Liberek, B. Rocz. Chem. 45, 967ā980 (1971).
Shriner, R. L. & Land, A. H. J. org. Chem. 6, 888ā894 (1941); Greenberg, D. M. & Schulman, M. P. Science 106, 271 (1947).
Chambers, J. R. & Isbell, A. F. J. org. Chem. 29, 832ā836 (1964).
Guze, L. B. in Microbial Protoplasts, Spheroplasts and L-forms (Williams & Wilkins, Baltimore, 1968).
Lorian, V. & Atkinson, B. Antimic. Ag. Chemother. 11, 541ā552 (1977).
Lorian, V. & Atkinson, B. Antimic. Ag. Chemother. 9, 1043ā1055 (1976).
Payne, J. W. Adv. microb. Physiol. 13, 55ā113 (1976).
Lambert, M. P. & Neuhaus, F. C. J. Bact. 110, 978ā987 (1972).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
ALLEN, J., ATHERTON, F., HALL, M. et al. Phosphonopeptides, a new class of synthetic antibacterial agents. Nature 272, 56ā58 (1978). https://doi.org/10.1038/272056a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/272056a0
This article is cited by
-
An efficient synthesis of functionalized Ī²-amino- and Ī²-hydrazinoalkylphosphonates by three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and aromatic amines or hydrazines
Molecular Diversity (2024)
-
A study of fungicidal and anti-phenol oxidase activity of some Ī±-amino phosphonate derivatives
Chemical and Biological Technologies in Agriculture (2021)
-
New chiral 1,4,2-oxazaphosphorinanes bearing a free hydroxy group
Russian Chemical Bulletin (2021)
-
Green synthesis of novel phosphonate derivatives using ultrasonic irradiation
Chemistry of Heterocyclic Compounds (2020)
-
(Some) current concepts in antibacterial drug discovery
Applied Microbiology and Biotechnology (2018)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
