Skip to main content
NCBI home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1965 Oct;54(4):1133–1141. doi: 10.1073/pnas.54.4.1133

Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine.

D J Tipper, J L Strominger
PMCID: PMC219812  PMID: 5219821

Full text

PDF
1133

Images in this article

1137Image
on p.1137

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ANDERSON J. S., MATSUHASHI M., HASKIN M. A., STROMINGER J. L. LIPID-PHOSPHOACETYLMURAMYL-PENTAPEPTIDE AND LIPID-PHOSPHODISACCHARIDE-PENTAPEPTIDE: PRESUMED MEMBRANE TRANSPORT INTERMEDIATES IN CELL WALL SYNTHESIS. Proc Natl Acad Sci U S A. 1965 Apr;53:881–889. doi: 10.1073/pnas.53.4.881. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BRUNETTI P., JOURDIAN G. W., ROSEMAN S. The sialic acids. III. Distribution and properties of animal N-acetylneuraminic aldolase. J Biol Chem. 1962 Aug;237:2447–2453. [PubMed] [Google Scholar]
  3. CHATTERJEE A. N., PARK J. T. BIOSYNTHESIS OF CELL WALL MUCOPEPTIDE BY A PARTICULATE FRACTION FROM STAPHYLOCOCCUS AUREUS. Proc Natl Acad Sci U S A. 1964 Jan;51:9–16. doi: 10.1073/pnas.51.1.9. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. CIAK J., HAHN F. E. Penicillin-induced lysis of Escherichia coli. Science. 1957 Jan 18;125(3238):119–120. doi: 10.1126/science.125.3238.119. [DOI] [PubMed] [Google Scholar]
  5. COLLINS J. F., RICHMOND M. H. A structural similarity between N-acetylmuramic acid and penicillin as a basis for antibiotic action. Nature. 1962 Jul 14;195:142–143. doi: 10.1038/195142a0. [DOI] [PubMed] [Google Scholar]
  6. DUERKSEN J. D. LOCALIZATION OF THE SITE OF FIXATION OF THE INDUCER, PENICILLIN, IN BACILLUS CEREUS. Biochim Biophys Acta. 1964 May 18;87:123–140. doi: 10.1016/0926-6550(64)90053-2. [DOI] [PubMed] [Google Scholar]
  7. ENSIGN J. C., WOLFE R. S. LYSIS OF BACTERIAL CELL WALLS BY AN ENZYME ISOLATED FROM A MYXOBACTER. J Bacteriol. 1965 Aug;90:395–402. doi: 10.1128/jb.90.2.395-402.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. GHUYSEN J. M., STROMINGER J. L. STRUCTURE OF THE CELL WALL OF STAPHYLOCOCCUS AUREUS, STRAIN COPENHAGEN. I. PREPARATION OF FRAGMENTS BY ENZYMATIC HYDROLYSIS. Biochemistry. 1963 Sep-Oct;2:1110–1119. doi: 10.1021/bi00905a035. [DOI] [PubMed] [Google Scholar]
  9. GHUYSEN J. M. [Data on the structure of disaccharide-peptide complexes liberated from the wall of Micrococcus lysodeikticus by the action of beta(1-4)N-acetylhexosaminidases]. Biochim Biophys Acta. 1961 Mar 4;47:561–568. doi: 10.1016/0006-3002(61)90551-0. [DOI] [PubMed] [Google Scholar]
  10. HASH J. H. PURIFICATION AND PROPERTIES OF STAPHYLOLYTIC ENZYMES FROM CHALAROPSIS SP. Arch Biochem Biophys. 1963 Sep;102:379–388. doi: 10.1016/0003-9861(63)90245-5. [DOI] [PubMed] [Google Scholar]
  11. HENDLIN D., SOARS M. H. The effect of 5,6-dimethylbenzimidazole and related compounds on the growth of Lactobacillus lactis Dorner. J Bacteriol. 1951 Nov;62(5):633–638. doi: 10.1128/jb.62.5.633-638.1951. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Kagan H. M., Manning L. R., Meister A. Stereospecific synthesis of alpha-methyl-L-glutamine by glutamine synthetase. Biochemistry. 1965 Jun;4(6):1063–1068. doi: 10.1021/bi00882a013. [DOI] [PubMed] [Google Scholar]
  13. Lederberg J. BACTERIAL PROTOPLASTS INDUCED BY PENICILLIN. Proc Natl Acad Sci U S A. 1956 Sep;42(9):574–577. doi: 10.1073/pnas.42.9.574. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. MARTIN H. H. COMPOSITION OF THE MUCOPOLYMER IN CELL WALLS OF THE UNSTABLE AND STABLE L-FORM OF PROTEUS MIRABILIS. J Gen Microbiol. 1964 Sep;36:441–450. doi: 10.1099/00221287-36-3-441. [DOI] [PubMed] [Google Scholar]
  15. Matsuhashi M., Dietrich C. P., Strominger J. L. Incorporation of glycine into the cell wall glycopeptide in Staphylococcus aureus: role of sRNA and lipid intermediates. Proc Natl Acad Sci U S A. 1965 Aug;54(2):587–594. doi: 10.1073/pnas.54.2.587. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Meadow P. M., Anderson J. S., Strominger J. L. Enzymatic polymerization of UDP-acetylmuramyl.L-ala.D-glu.L-lys.D-ala.D-ala and UDP-acetylglucosamine by a particulate enzyme from Staphylococcus aureus and its inhibition by antibiotics. Biochem Biophys Res Commun. 1964;14:382–387. doi: 10.1016/s0006-291x(64)80014-0. [DOI] [PubMed] [Google Scholar]
  17. PRIMOSIGH J., PELZER H., MAASS D., WEIDEL W. Chemical characterization of mucopeptides released from the E. coli B cell wall by enzymic action. Biochim Biophys Acta. 1961 Jan 1;46:68–80. doi: 10.1016/0006-3002(61)90647-3. [DOI] [PubMed] [Google Scholar]
  18. ROGERS H. J., JELJASZEWICZ J. Inhibition of the biosynthesis of cell-wall mucopeptides by the penicillins. A study of penicillin-sensitive and penicillin-resistant strains of Staphylococcus aureus. Biochem J. 1961 Dec;81:576–584. doi: 10.1042/bj0810576. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. SALTON M. R. J. Cell wall of Micrococcus lysodeikticus as the substrate of lysozyme. Nature. 1952 Nov 1;170(4331):746–747. doi: 10.1038/170746a0. [DOI] [PubMed] [Google Scholar]
  20. SALTON M. R. Studies of the bacterial cell wall. VIII. Reaction of walls with hydrazine and with fluorodinitrobenzene. Biochim Biophys Acta. 1961 Sep 16;52:329–342. doi: 10.1016/0006-3002(61)90682-5. [DOI] [PubMed] [Google Scholar]
  21. STROMINGER J. L., PARK J. T., THOMPSON R. E. Composition of the cell wall of Staphylococcus aureus: its relation to the mechanism of action of penicillin. J Biol Chem. 1959 Dec;234:3263–3268. [PubMed] [Google Scholar]
  22. STRUVE W. G., NEUHAUS F. C. EVIDENCE FOR AN INITIAL ACCEPTOR OF UDP-NAC-MURAMYL-PENTAPEPTIDE IN THE SYNTHESIS OF BACTERIAL MUCOPEPTIDE. Biochem Biophys Res Commun. 1965 Jan 4;18:6–12. doi: 10.1016/0006-291x(65)90873-9. [DOI] [PubMed] [Google Scholar]
  23. TERNBERG J. L., HERSHEY F. B. Colorimetric determination of blood ammonia. J Lab Clin Med. 1960 Nov;56:766–776. [PubMed] [Google Scholar]
  24. TIPPER D. J., STROMINGER J. L., GHUYSEN J. M. STAPHYLOLYTIC ENZYME FROM CHALAROPSIS: MECHANISM OF ACTION. Science. 1964 Nov 6;146(3645):781–782. doi: 10.1126/science.146.3645.781. [DOI] [PubMed] [Google Scholar]
  25. WEIBULL C. The isolation of protoplasts from Bacillus megaterium by controlled treatment with lysozyme. J Bacteriol. 1953 Dec;66(6):688–695. doi: 10.1128/jb.66.6.688-695.1953. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. Wise E. M., Jr, Park J. T. Penicillin: its basic site of action as an inhibitor of a peptide cross-linking reaction in cell wall mucopeptide synthesis. Proc Natl Acad Sci U S A. 1965 Jul;54(1):75–81. doi: 10.1073/pnas.54.1.75. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES