Chemistry of Natural Compounds

, Volume 21, Issue 5, pp 553–566 | Cite as

Chemical modification of the arginine residues of proteins and peptides

  • V. M. Makhnyr
Article
  • 172 Downloads

Abstract

Methods for the chemical modification of arginine residues with the aid of butan-2,3-dione and its oligomers, cyclohexane-1,2-dione, phenylglyoxal, tetraethoxy-propane, nitromalondialdehyde, and pentane-2,4-dione are considered. The conditions for performing the reactions and their mechanism are given and the stability of the products formed and methods for their identification are discussed.

Keywords

Arginine Borate Dione Ornithine Acetylacetone 

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Literature cited

  1. 1.
    H. Durgas and C. Penney, Bioorganic Chemistry. A Chemical Approach to Enzyme Action, Springer, New York (1981).Google Scholar
  2. 2.
    C.L. Borders, J. F. Riordan and D. S. Auld, Biochem. Biophys. Res. Commun.,66, 490 (1975).PubMedCrossRefGoogle Scholar
  3. 3.
    J. F. Riordan, Biochemistry,12, 3915 (1973).PubMedCrossRefGoogle Scholar
  4. 4.
    F. J. Daemen and J. F. Riordan, Biochemistry,13, 2865 (1974).PubMedCrossRefGoogle Scholar
  5. 5.
    J. Berghauser, Biochim. Biophys. Acta,397, 370 (1975).PubMedGoogle Scholar
  6. 6.
    S. Yamada and H. A. Itano, Biochim. Biophys. Acta,130, 538 (1966).PubMedGoogle Scholar
  7. 7.
    S. Tanabe, T. Oya, and T. Sakaguchi, Chem. Pharm. Bull.,23, 1657 (1975).Google Scholar
  8. 8.
    J. A. Yankeelov, Methods Enzymol.,25, 566 (1972).CrossRefGoogle Scholar
  9. 9.
    L. G. Lange, J. F. Riordan, B. L. Vallee, and C. I. Branden, Biochemistry,14, 3497 (1975).PubMedCrossRefGoogle Scholar
  10. 10.
    P. Gacesa, M. J. Savitsky, K. S. Dodgson, and A. H. Olavesen, Biochim. Biophys. Acta,661, 205 (1981).PubMedGoogle Scholar
  11. 11.
    D. P. Malinowski and I. Fridovich, Biochemistry,18, 5909 (1979).PubMedCrossRefGoogle Scholar
  12. 12.
    J. A. Yankeelov, C. D. Mitchell, and T. H. Crawford, J. Am. Chem. Soc.,90, 1664 (1968).PubMedCrossRefGoogle Scholar
  13. 13.
    J. A. Yankeelov and D. Acree, Biochem. Biophys. Res. Commun.,42, 886 (1971).PubMedCrossRefGoogle Scholar
  14. 14.
    J. A. Yankeelov, Biochemistry,9, 2433 (1970).PubMedCrossRefGoogle Scholar
  15. 15.
    K. Toi, E. Bynum, E. Norris, and H. A. Itano, J. Biol. Chem.,240, PC 3455 (1965).Google Scholar
  16. 16.
    K. Toi, E. Bynum, E. Norris, and H. A. Itano, J. Biol. Chem.,242, 1036 (1967).PubMedGoogle Scholar
  17. 17.
    L. Patty and E. L. Smith, J. Biol. Chem.,250, 557 (1975).Google Scholar
  18. 18.
    B. M. Martin, B. A. Chibber, and A. Maelicke, J. Biol. Chem.,258, 8714 (1983).PubMedGoogle Scholar
  19. 19.
    L. Patty, E. L. Smith, J. Biol. Chem.,250, 565 (1975).Google Scholar
  20. 20.
    U. R. Apsalon and A. I. Miroshnikov, Bioorg. Khim.,6, 773 (1980).Google Scholar
  21. 21.
    E. Humble, Acta Chem. Scand.,B33, 705 (1979).CrossRefGoogle Scholar
  22. 22.
    K. Takahashi, J. Biol. Chem.,243, 6171 (1968).PubMedGoogle Scholar
  23. 23.
    K. K. Nakaya, H. Horinishi, and K. Shibata, J. Biochem. (Tokyo),61, 345 (1967).PubMedGoogle Scholar
  24. 24.
    K. Takahashi, J. Biochem.,81, 403 (1977).PubMedGoogle Scholar
  25. 25.
    C. L. Borders and J. F. Riordan, Biochemistry,14, 4699 (1975).PubMedCrossRefGoogle Scholar
  26. 26.
    M. Phillips, D. B. Pho, and L.-A. Pradel, Biochim. Biophys. Acta,566, 296 (1979).Google Scholar
  27. 27.
    S. E. Kebbaj, N. Latruffe, and Y. Gaudemer, Biochem. Biophys. Res. Commun.,108, 42 (1982).PubMedCrossRefGoogle Scholar
  28. 28.
    C. C. Yang, C. C. Chang, and I. F. Liou, Biochim. Biophys. Acta,365, 1 (1974).PubMedGoogle Scholar
  29. 29.
    M. M. Werber, M. Moldovan, and M. Sokolovsky, Eur. J. Biochem.,53, 207 (1975).CrossRefGoogle Scholar
  30. 30.
    R. B. Yamasaki, A. Vega, and R. E. Feeney, Anal. Biochem.,109, 32 (1980).PubMedCrossRefGoogle Scholar
  31. 31.
    T. P. King, Biochemistry,5, 3454 (1966).PubMedCrossRefGoogle Scholar
  32. 32.
    A. V. Muranov and N. N. Modyanov, Bioorg. Khim.,5, 210 (1979).Google Scholar
  33. 33.
    E. Kozlovskaya, H. Vozhova, and G. Elyakov, Chem. Peptides Proteins,1, 379 (1982).Google Scholar
  34. 34.
    A. Signor, G. M. Bonora, L. Biondi, D. Nisato, A. Marzotto and E. Scoffone, Biochemistry,10, 2748 (1971).PubMedCrossRefGoogle Scholar
  35. 35.
    H. F. Gilbert and M. H. O'Leary, Biochemistry,14, 5194 (1975).PubMedCrossRefGoogle Scholar
  36. 36.
    G. Tunnicliff and T. T. Ngo, Experientia,34, 989 (1978).PubMedCrossRefGoogle Scholar

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© Plenum Publishing Corporation 1986

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  • V. M. Makhnyr

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