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Chemistry of Natural Compounds

, Volume 25, Issue 3, pp 331–334 | Cite as

Unusual result of modification of anemonotoxin RTX-III by malonaldehyde

  • V. M. Makhnyr'
  • É. P. Kozlovskaya
Article

Abstract

The modification of the arginine residues of neurotoxin RTX-III fromRadianthus macrodactylus with malonaldehyde led to the formation of a derivative with a maximum in the UV spectrum at 340 nm in place of the expected Nδ-(pyrimidin-2-yl)ornithine with absorption at 315 nm. On the basis of chemical transformations and the results of absorption spectroscopy, it has been concluded that the product obtained was an intermediate of the reaction — a Schiff's base. It has been shown that the stabilization of the reactive intermediate is due to the influence of steric factors. The further conversion of the toxin derivative taking place in neutral and alkaline media has been investigated; it is connected with a rearrangement of the malonaldehyde residue of the enol-enamine type.

Keywords

Organic Chemistry Arginine Schiff Absorption Spectroscopy Ornithine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    T. P. King, Biochemistry,5, No. 11, 3454 (1966).Google Scholar
  2. 2.
    T. A. Zykova, L. M. Vinokurov, É. L. Kozlovskaya, and G. B. Elyakov, Bioorg. Khim.,11, No. 3, 302 (1985).Google Scholar
  3. 3.
    V. M. Makhnyr' and É. L. Kozlovskaya, Abstracts of Lectures at the VIIth All-Union Symposium on the Chemistry of Proteins and Peptides [in Russian], Tallin (1987), p. 70.Google Scholar
  4. 4.
    A. V. Muranov and M. N. Modyanov, Bioorg. Khim.,5, No. 2, 210 (1979).Google Scholar
  5. 5.
    P. Sykes, A Guidebook to Mechanisms in Organic Chemistry, 4th edn., Longmans, London 1975 [Russian translation, Khimiya, Moscow (1977), p. 259]Google Scholar
  6. 6.
    C. Largillierre and S. B. Melancon, Anal. Biochem.,170, 123 (1988).Google Scholar
  7. 7.
    R. Fields and H. B. F. Dixon, Biochem. J.,121, No. 4, 587 (1971).Google Scholar
  8. 8.
    G. Romey and J.-P. Abita, H. Schweitz, G. Wanderer, and M. Lazdunski, Proc. Natl. Acad. Sci. USA,73, No. 11, 4055 (1976).Google Scholar
  9. 9.
    F. Miranda, H. Rochat, C. Rochat, and S. Lissitzky, Eur. J. Biochem.,16, 514 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • V. M. Makhnyr'
  • É. P. Kozlovskaya

There are no affiliations available

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