Skip to main content

Evaluation of Novel Inhibitors of ACC Oxidase Possessing Cyclopropyl Moiety

  • Chapter
Biology and Biotechnology of the Plant Hormone Ethylene II

Abstract

Ethylene production is inhibited by several new structural analogues of amino cyclopropane carboxylic acid (ACC), without an amine function in the C1 position. The Substituted Cyclopropane Carboxylic Acids (SCCA) require a minimal cyclopropane ring but no amine function to exhibit inhibition. Ethylene inhibition was essayed on tomato discs, and on partially purified ACC oxidase from apple fruits. These new inhibitors possess a cyclopropane ring and a substituant (R2) in the C2 position. First results showed that the amount of ethylene inhibition is strongly correlated to the chemical structure of (R2, R5) and to the presence or not of a carboxylic function in the C1 position of the cyclopropane ring. To evaluate the nature of inhibition, kinetic studies were made using partially purified ACC oxidase from apple fruits. From all the inhibitors tested the best results were obtained using trans — phenyl cyclopropane carboxylic acid and cyclopropane 1,1 dicarboxylic acid.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover 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

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Yang, S.F. and Hoffman, N.E. (1984) Ethylene biosynthesis and its regulation in higher plants, Annu. Rev. Plant Physiol. 35, 155–189

    Article  CAS  Google Scholar 

  2. Dong, J.G., Olson, D., Silverstone, A. and Yang, S.F. (1992) Sequence of a cDNA coding for a l-aminocyclopropane-1-carboxylate oxidase homolog from apple fruit, Plant Physiol. 98, 1530–1531

    Article  PubMed  CAS  Google Scholar 

  3. Fernandez-Maculet, J.C. and Yang, S.F. (1992) Extraction and partial characterization of the ethylene-forming enzyme from apple fruit, Plant Physiol. 99, 751–754

    Article  PubMed  CAS  Google Scholar 

  4. Ververidis, P. and John, P. (1991) Complete recovery in vitro of ethylene-forming enzyme activity, Phytochemistry 30, 725–727

    Article  CAS  Google Scholar 

  5. Dupille, E., Latché, A., Roques, C. and Pech, J.C. (1992) Stabilization in vitro et purification de l’enzyme formant l’ethylene chez la pomme, C.R. Acad. Sci. Paris, Série III, t 315, 77–84

    CAS  Google Scholar 

  6. McGarvey, L. and Christoffersen, R.E. (1992) Characterization and kinetic parameters of ethylene-forming enzyme from avocado fruit, J. Biol. Chem. 267, 5962–5967

    Google Scholar 

  7. Charng, Y.-Y., Dong, J.-G. and Yang, S.F. (1996) Structure-function studies on the l-aminocyclopropane-1-carboxylic acid (ACC) oxidase carbon dioxide binding site, in NATO Advanced Research Workshop, Biology and Biotechnology of the Plant Hormone Ethylene, June 9-13, Chania, Crete, Greece

    Google Scholar 

  8. Dilley, D.R., Wilson, I.D., Burmeister, D.M., Kuai, J. Poneleit L., Zhu, Y., Pekker, Y. Gran, C. and Bower, A. (1993) Purification and characterization of ACC oxidase and its expression during ripening in apple fruit, in J. C. Pech et al. (eds.), Cellular and Molecular Aspects of the Plant Hormone Ethylene, Kluwer Academic Publishers, Dordrecht, pp. 46–52.

    Google Scholar 

  9. Dong, J.G., Femandez-Maculet, J.C. and Yang, S.F. (1992) Purification and characterization of l-aminocyclopropane-1-carboxylate oxidase from ripe apple fruit, Proc. Natl. Acad. Sci. USA 89, 9789–9793.

    Article  PubMed  CAS  Google Scholar 

  10. Femandez-Maculet, J.C. and Yang, S.F. (1993) Activation of l-aminocyclopropane-l-carboxylate oxidase by carbon dioxide, Biochem. Biophys. Res. Comm. 193, 1168–1173.

    Article  Google Scholar 

  11. Dupille, E., Rombaldi, C., Leliévre, J.M., Cleyet-Marel, J.C., Pech, J.C. and Latché, A. (1993) Purification, properties and partial amino-acid sequence of l-aminocyclopropane-l-carboxylic acid oxidise from apple fruits, Planta 190:65–70.

    Article  PubMed  CAS  Google Scholar 

  12. Barlow, J., Zhang, Z., John, P., Baldwin, J.E. and Schofield, C.J. (1997) Inactivation of 1-Aminocyclopropane-1-carboxylate oxidase involves oxidative modifications, Biochemistry, 36, 3563–3569.

    Article  PubMed  CAS  Google Scholar 

  13. Zhang Z. H., Barlow J.N., Baldwin J.E. and Schofield C. (1998) Metal-catalysed oxidation and mutagenesis studies on the iron (II) binding site of l-aminocyclopropane-l-carboxylate oxidase, Biochemistry, 36, 15999–16007.

    Article  Google Scholar 

  14. Pirrung, M.C., Kaiser, L.M. and Chen, J. (1993) Purification and properties of the apple fruit ethylene-forming enzyme, Biochemistry, 32, 7445–7450.

    Article  PubMed  CAS  Google Scholar 

  15. Kadyrzhanova, D.K, McCully, T.J., Jaworski, S.A., Verderidis P., Vlachonasios K.E., Murakami, K.J. and Dilley, D.R. (1997) Structure-function analysis of ACC oxidase by site-directed mutagenesis, in A.K. Kanellis et al. (eds.), Biology and Biotechnology of the Plant Hormone Ethylene, Kluwer Academic Publishers, Dordrecht, pp. 5–13.

    Chapter  Google Scholar 

  16. John, P., Iturriagagoitia-Bueno, T., Lay, V., Thomas, P.G., Hedderson, T.A.J., Prescott, A.G., Gibson, E.G. and Schofield, C.J. (1997) 1-Aminocyclopropane-1-carboxylate oxidase: Molecular structure and catalytic function, in A.K. Kanellis et al. (eds.), Biology and Biotechnology of the Plant Hormone Ethylene, Kluwer Academic Publishers, Dordrecht, pp. 15–21.

    Chapter  Google Scholar 

  17. Charng, Y., Lui, Y., Dong, J.G. and Yang, S.F. (1997) On 1-aminocyclopropane-1-carboxylic acid (ACC) Oxidase, in A.K. Kanellis et al. (eds.), Biology and Biotechnology of the Plant Hormone Ethylene, Kluwer Academic Publishers, Dordrecht, pp. 23–29

    Chapter  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Dourtoglou, V., Koussissi, E., Petritis, K. (1999). Evaluation of Novel Inhibitors of ACC Oxidase Possessing Cyclopropyl Moiety. In: Kanellis, A.K., Chang, C., Klee, H., Bleecker, A.B., Pech, J.C., Grierson, D. (eds) Biology and Biotechnology of the Plant Hormone Ethylene II. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4453-7_3

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-4453-7_3

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5910-7

  • Online ISBN: 978-94-011-4453-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics