Skip to main content
SpringerLink
Log in
Book cover

Mechanism of Action of Antimicrobial and Antitumor Agents pp 448–458Cite as

Gougerotin

  • Chapter

Part of the book series: Antibiotics ((ANTIBIOTICS,volume 3))

Abstract

Gougerotin is a water-soluble basic antibiotic obtained from culture filtrate of Streptomyces gougerotii No. 21544, isolated from a soil sample in Kyoto by workers at the Takeda Chemical Industries, Ltd., Osaka, Japan (Kanzaki et al., 1962). Gougerotin is a broad spectrum but weak antibiotic and inhibits Gram-positive, Gram-negative bacteria and mycobacteria. Yeasts and fungi are not inhibited (Table 1). Gougerotin inhibits the growth of Pseudorabies, vaccinia, Newcastle disease, fowl plague, and Western equine encephalomyelitis viruses (Thiry, 1968). The LD50 for mice is 57 mg/Kg by intravenous route (Kanzaki et al., 1962).

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

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Allen, D. W., and P. C. Zamecnik: The effect of puromycin on rabbit reticulocyte ribosomes. Biochim. Biophys. Acta 55, 865 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Capecchi, M. R., and H. A. Klein: Characterization of three proteins involved in polypeptide chain termination. Cold Spring Harbor Symp. Quant. Biol. 34, 469 (1969).

    Article  CAS  Google Scholar 

  • Casjens, S. R., and A. J. Morris: The selective inhibition of protein assembly by gougerotin. Biochim. Biophys. Acta 108, 677 (1965).

    PubMed  CAS  Google Scholar 

  • Celma, M. L., R. E. Monro, and D. Vazquez: Substrate and antibiotic binding sites at the peptidyl transferase centre of E. coli ribosomes. FEBS Letters 6, 273 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Cerna, J., F. W. Lichtenthaler, and I. Rychlik: The effect of gougerotin analogues on ribosomal peptidyl transferase, FEBS Letters 14, 45 (1971).

    Article  PubMed  CAS  Google Scholar 

  • Clark, J. M., Jr.: Gougerotin. In: Antibiotics, vol. 1, (eds. D. Gottlieb and P. D. Shaw) p. 278. Berlin-Heidelberg-New York: Springer 1967.

    Google Scholar 

  • Clark, J. M., Jr., and A. Y. Chang: Inhibitors of the transfer of amino acids from aminoacyl soluble ribonucleic acid to protein. J. Biol. Chem. 240, 4734 (1965).

    PubMed  CAS  Google Scholar 

  • Clark, J. M., Jr., and J. K. Gunther: Gougerotin, a specific inhibitor of protein synthesis. Biochim. Biophys. Acta 76, 636 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Coutsogeorgopoulos, C.: Amino acylaminonucleoside inhibitors of protein synthesis. The effect of amino acyl ribonucleic acid on the inhibition. Biochemistry 6, 1704 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Coutsogeorgopoulos, C: Formation of oligophenylalanine in the presence of certain inhibitors of protein synthesis. Federation Proc. 28, 844 (1969).

    Google Scholar 

  • Coutsogeorgopoulos, C.: On the inhibition of ribosome-catalyzed peptide bond formation by certain antibiotics. Proc. 6th Intern. Congr. Chemotherapy, Tokyo, p. 482, 1970.

    Google Scholar 

  • Dixon, M., and E. C. Webb: Enzymes. London: Longmans, 1964.

    Google Scholar 

  • Fahnestock, S., H. Neumann, V. Shashoua, and A. Rich: Ribosome-catalyzed ester formation. Biochemistry 9, 2477 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Fox, J. J., Y. Kuwada, and K. A. Watanabe: Nucleosides. LVI. Structure of nucleoside antibiotic, gougerotin. Tetrahedron Letters 1968, 6029.

    Google Scholar 

  • Fox, J. J., Y. Kuwada, K. A. Watanabe, T. Ueda, and E. B. Whipple: Nucleosides. XXV. Chemistry of gougerotin. Antimicrobial Agents chemotherapy 1964, 518.

    Google Scholar 

  • Fox, J. J., and K. A. Watanabe: Studies directed towards the total synthesis of the nucleoside antibiotics, gougerotin and blasticidin S. Pure Appl. Chem. 28, 475 (1971).

    Article  PubMed  CAS  Google Scholar 

  • Fox, J. J., K. A. Watanabe, and A. Bloch: Nucleoside antibiotics. Progr. Nucleic Acid Res. Mol. Biol. 5, 251 (1966).

    Article  CAS  Google Scholar 

  • Gilbert, W.: Polypeptide synthesis in Escherichia coli. II. The polypeptide chain and sRNA. J. Mol. Biol. 6, 389 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Goldberg, I. H., and K. Mitsugi: Inhibition by sparsomycin and other antibiotics of the puromycin- induced release of polypeptide from ribosomes. Biochemistry 6, 383 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Gottesman, M. E.: Reaction of ribosome-bound peptidyl transfer ribonucleic acid with aminoacyl transfer ribonucleic acid or puromycin. J. Biol. Chem. 242, 5564 (1967).

    PubMed  CAS  Google Scholar 

  • Herner, A. E., I. H. Goldberg, and L. B. Cohen: Stabilization of N-acetyl-phenylalanyl transfer ribonucleic acid binding to ribosomes by sparsomycin. Biochemistry 8, 1335 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Iwasaki, H.: Studies on the structure of gougerotin. XI. Structure of gougerotin. Yakugaku Zasshi 82, 1393 (1962).

    CAS  Google Scholar 

  • Jayaraman, J., and I. H. Goldberg: Localization of sparsomycin action to the peptide-bond-forming step. Biochemistry 7, 418 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Jimenez, A., R. E. Monro, and D. Vazquez: Interaction of Ac-Phe- tRNA with E. coli ribosomal subunits. 1. Sparsomycin-induced formation of a complex containing 50S and 30S subunits but not mRNA. FEBS Letters 7, 103 (1970a).

    Article  PubMed  CAS  Google Scholar 

  • Jimenez, A., R. E. Monro, and D. Vazquez: Interaction of Ac-Phe-tRNA with E. coli ribosomal subunits. 2. Resistance of the sparsomycin-induced complex to hydroxylamine action. FEBS Letters 7, 109 (1970b).

    Article  PubMed  CAS  Google Scholar 

  • Kaji, A., K. Igarashi, and H. Ishitsuka: Interaction of tRNA with ribosomes, Binding and release of tRNA. Cold Spring Harbor Symp. Quant. Biol. 34, 167 (1969).

    Article  CAS  Google Scholar 

  • Kanzaki, T., E. Higashide, H. Yamamoto, M. Shibata, K. Nakazawa, H. Iwasaki, T. Takewaka, and A. Miyake: Gougerotin, a new antibacterial antibiotic. J. Antibiotics (Tokyo), Ser. A 15, 93 (1962).

    CAS  Google Scholar 

  • Korzybski, T., Z. Kowszyk-Gindifer, and W. Kurylowicz: Antibiotics, vol.1, Origin, nature and properties. New York: Pergamon Press 1967.

    Google Scholar 

  • Lichtenthaler, F. W., G. Trummlitz, G. Bambach, and I. Rychlik: Nucleosides. XI. Synthesis of a biologically active gougerotin analogue. Angew. Chem. 10, 334 (1971).

    Article  CAS  Google Scholar 

  • Lichtenthaler, F. W., G. Trummlitz, and P. Emig: Nucleosides. X. Synthesis of dipeptidyl amino sugar nucleosides structurally related to gougerotin. Tetrahedron Letters 1970, 2061.

    Google Scholar 

  • Lucas-Lenard, J., and A. L. Haenni: Requirement of guanosine 5′-triphosphate for ribosomal binding of aminoacyl-sRNA. Proc. Natl. Acad. Sci. U.S. 59, 554 (1968).

    Article  CAS  Google Scholar 

  • Monro, R. E.: Catalysis of peptide bond formation by 50S ribosomal subunits from Escherichia coli. J. Mol. Biol. 26, 147 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Monro, R. E., M. L. Celma, and D. Vazquez: Action of sparsomycin on ribosome-catalysed peptidyl transfer. Nature 222, 356 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Monro, R. E., J. Cerna, and K. A. Marcker: Ribosome-catalyzed peptidyl transfer: Substrate specificity at the P-site. Proc. Natl. Acad. Sci. U.S. 61, 1042 (1968).

    Article  CAS  Google Scholar 

  • Monro, R. E., and K. A. Marcker: Ribosome-catalyzed reaction of puromycin with a formylmethionine- containing oligonucleotide, J. Mol. Biol. 25, 347 (1967).

    Article  CAS  Google Scholar 

  • Monro, R. E., T. Staehelin, M. L. Celma, and D. Vazquez: The peptidyl transferase activity of ribosomes. Cold Spring Harbor Symp. Quant. Biol. 34, 357 (1969).

    Article  CAS  Google Scholar 

  • Monro, R. E., and D. Vazquez: Ribosome-catalysed peptidyl transfer: Effects of some inhibitors of protein synthesis. J. Mol. Biol. 28, 161 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Nathans, D., J. E. Allende, T. W. Conway, G. I. Spyrides, and F. Lipmann: Protein synthesis from aminoacyl-sRNA’s. Symposium on Information Macromolecules (H. J. Vogel, V. Bryson and J. O. Lampen, eds). Academic Press: New York 1963.

    Google Scholar 

  • Nathans, D., and A. Neidle: Structural requirements for puromycin inhibition of protein synthesis. Nature 197, 1076 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Nirenberg, M. W., J. H. Matthae, and O. W. Jones: An intermediate in the biosynthesis of polyphenylalanine directed by synthetic template RNA. Proc. Natl. Acad. Sic. U.S. 48, 104 (1962).

    Article  CAS  Google Scholar 

  • Pestka, S.: Studies on the formation of transfer ribonucleic acid-ribosome complexes, XI. Antibiotic effects on phenylalanyl-oligonucleotide binding to ribosomes. Proc. Natl. Acad. Sci. U.S. 64, 709 (1969 a).

    Article  CAS  Google Scholar 

  • Pestka, S.: Translocation, aminoacyl-oligonucleotides, and antibiotic action. Cold Spring Harbor Symp. Quant. Biol. 34, 395 (1969 b).

    Article  CAS  Google Scholar 

  • Pestka. S.: Studies on the formation of transfer ribonucleic acid-ribosome complexes, VIII. Survey of the effect of antibiotics on N-acetyl-phenylalanyl-puromycin formation: Possible mechanism of chloramphenicol action. Arch. Biochem. Biophys. 136, 80 (1970 a).

    Article  PubMed  CAS  Google Scholar 

  • Pestka, S.: Studies on the formation of transfer ribonucleic cid-ribosome complexes, IX. Effect of antibiotics on translocation and peptide bond formation. Arch. Biochem. Biophys. 136, 89 (1970 b).

    Article  PubMed  CAS  Google Scholar 

  • Pestka, S.: Inhibitors of ribosome functions. Ann. Rev. Biochem. 40, 697 (1971).

    Article  Google Scholar 

  • Sinohara, H., and H. H. Sky-Peck: Effect of gougerotin on the protein synthesis in the mouse liver. Biochem. Biophys. Res. Commun. 18, 98 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Suhadolnik, R. J.: Nucleoside antibiotics. New York: Wiley-Interscience 1970.

    Google Scholar 

  • Thiry, L.: The action of sparsomycin and gougerotin on virus growth. J. Gen. Virol. 2, 143 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Vazquez, D., E. Battaner, R. Neth, G. Heller, and R. E. Monro: The function of 80S ribosomal subunits and effects of some antibiotics. Cold Spring Harbor Symp. Quant. Biol. 34, 369 (1969).

    Article  CAS  Google Scholar 

  • Yukioka, M., and S. Morisawa: Studies on the mechanism of action of gougerotin. I. Enhancement of polyphenylalanine synthesis by gougerotin. J. Biochem. (Tokyo) 66, 225 (1969a).

    CAS  Google Scholar 

  • Yukioka, M., and S. Morisawa: Studies on the mechanism of action of gougerotin. II. Effect of various factors on gougerotin action. J. Biochem. (Tokyo) 66, 233 (1969b).

    CAS  Google Scholar 

  • Yukioka, M., and S. Morisawa: Studies on the mechanism of action of gougerotin. III. Enhancement of enzymatic binding of phenylalanyl-tRNA to ribosomes by gougerotin. J Biochem. (Tokyo) 66, 241 (1969c).

    CAS  Google Scholar 

  • Yukioka, M., and Morisawa: Manuscript in preparation.

    Google Scholar 

Download references

Authors
  1. Munehiko Yukioka
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Biochemistry, The Medical and Dental Schools, Northwestern University, 303 E. Chicago Avenue, Chicago, Illinois, 60611, USA

    John W. Corcoran Ph.D.

  2. Department of the Army, Walter Reed Army Institute of Research, Walter Reed Army Medical Center, Washington, D.C., 20012, USA

    Fred E. Hahn Ph.D.

Rights and permissions

Reprints and permissions

Copyright information

© 1975 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Yukioka, M. (1975). Gougerotin. In: Corcoran, J.W., Hahn, F.E., Snell, J.F., Arora, K.L. (eds) Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46304-4_29

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-46304-4_29

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46306-8

  • Online ISBN: 978-3-642-46304-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation