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New Reaction of O-Benzoquinone at the Thioether Group of Methionine

Abstract

Ortho-quinones such as o-benzoquinone, DOPA quinone, indole-5,6-quinone, adrenoquinone and flavonol quinones are highly reactive and unstable compounds present in biological systems1. Their reactions with proteins are intimately connected with such biochemical processes as formation of melanin2–4, tanning of insect cuticle5, 6 and tanning of plant proteins7–9. The reaction of o-benzoquinone with some of the enzymes results in their inactivation10, 11. The principal functional groups of proteins that have been implicated in these cases are the amino, imino and the sulphydryl groups1. In our studies on the reaction of o-benzoquinone with amino-acids and proteins we have observed a new reaction of o-benzoquinone at the thioether group of methionine.

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References

  1. Mason, H. S., Adv. Enzymol., 16, 105 (1955).

    CAS  Google Scholar 

  2. Raper, H. S., J. Chem. Soc., 125 (1938).

  3. Mason, H. S., and Gordon, M., in Pigment Cell Growth, 277 (Academic Press, New York, 1953).

    Book  Google Scholar 

  4. Wagreich, H., and Nelson, J. H., J. Amer. Chem. Soc., 60, 1545 (1938).

    Article  CAS  Google Scholar 

  5. Fraenkel, G., and Rudall, K. M., Proc. Roy. Soc., B, 134, 111 (1947).

    CAS  Google Scholar 

  6. Hackmann, R. H., Biochem. J., 54, 371 (1953).

    Article  Google Scholar 

  7. Roberts, E. A. H., J. Sci. Food Agri., 5, 193 (1952).

    Article  Google Scholar 

  8. Roberts, E. A. H., and Wood, D. J., Biochem. J., 47, 173 (1950).

    Article  Google Scholar 

  9. Barau, A. N., and Roberts, E. A. H., Biochem. J., 34, 1524 (1940).

    Article  Google Scholar 

  10. Hoffmann Ostenoff, O., and Biach, E., Experientia, 2, 405 (1946).

    Article  Google Scholar 

  11. Hoffmann Ostenoff, O., and Gieren, S., Monatsch., 79, 379 (1948).

    Article  Google Scholar 

  12. Willstatter, R., and Pfannenstiel, A., Ber. Deutsch. Chem. Gesell., 37, 4744 (1904).

    Article  CAS  Google Scholar 

  13. Bordwell, F. G., and Boutan, P. J., J. Amer. Chem. Soc., 78, 87 (1950).

    Article  Google Scholar 

  14. Wanzlick, H. W., Newer Methods of Preparative Organic Chemistry (edit. by Foerst, W.), 4, 139 (Academic Press, New York and London, 1968).

    Google Scholar 

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VITHAYATHIL, P., MURTHY, G. New Reaction of O-Benzoquinone at the Thioether Group of Methionine. Nature New Biology 236, 101–103 (1972). https://doi.org/10.1038/newbio236101b0

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