Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Non-Enzymic Hydroxylation of Polycyclic Aromatic Hydrocarbons

Abstract

THE hydroxylation of aromatic compounds in vivo is well known1, and polycyclic aromatic hydrocarbons2 and aromatic amino-acids and related compounds3 have been found to be hydroxylated by suitably fortified suspensions of rodent liver microsomes. Aromatic amino-acids and related compounds are also hydroxylated non-enzymically in phosphate buffer solutions containing iron and ascorbic acid in the presence of oxygen4,5, or in hydrogen peroxide solutions containing Fe++ (ref. 6). In the case of polycyclic aromatic hydrocarbons slow conversion to quinones, by ascorbic acid7, and more rapid oxidation by hydrogen peroxide8, have been reported.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Parke, D. V., and Williams, R. T., Ann. Rep. Chem. Soc., 55, 376 (1959).

    Google Scholar 

  2. Conney, A. H., Miller, E. C., and Miller, J. A., J. Biol. Chem., 288, 753 (1957).

    Google Scholar 

  3. Mitoma, C., Posner, H. S., Reitz, H. C., and Udenfriend, S., Arch. Biochem. Biophys., 61, 431 (1956).

    Article  CAS  PubMed  Google Scholar 

  4. Udenfriend, S., Clark, C. T., Axelrod, J., and Brodie, B. B., J. Biol. Chem., 208, 731 (1954).

    CAS  PubMed  Google Scholar 

  5. Dalgliesh, C. E., Arch. Biochem. Biophys., 58, 214 (1955).

    Article  CAS  PubMed  Google Scholar 

  6. Raper, H. S., Biochem. J., 26, 2000 (1932).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Warren, F. L., Biochem. J., 37, 338 (1943).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Calcutt, G., Brit. J. Cancer, 4, 254 (1950).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Harper, K. H., Brit. J. Cancer, 13, 732 (1959).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Mazelis, M., Nature, 189, 305 (1961).

    Article  ADS  CAS  PubMed  Google Scholar 

  11. Baldwin, E., Dynamic Aspects of Biochemistry, third ed., 160 (Camb. Univ. Press, 1959).

    Google Scholar 

  12. Openheimer, C., and Stern, K. G., Biological Oxidation, 67 (W. Junk, The Hague, 1939).

    Book  Google Scholar 

  13. Emeléus, H. J., and Anderson, J. S., Modern Aspects of Inorganic Chemistry, second ed., 178 (Routledge and Kegan Paul, London, 1952).

    Google Scholar 

  14. Emeléus, H. J., and Anderson, J. S., Modern Aspects of Inorganic Chemistry, second ed., 183 (Routledge and Kegan Paul, London, 1952).

    Google Scholar 

  15. Harper, K. H., Brit. J. Cancer, 11, 499 (1957).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Norman, R. O. C., Thompson, G. A., and Waters, W. A., J. Chem. Soc., 175 (1958).

  17. Friedel, R. A., and Orchin, M., Ultra-violet Spectra of Aromatic Compounds (Chapman and Hall, London, 1951).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

DEWHURST, F., CALCUTT, G. Non-Enzymic Hydroxylation of Polycyclic Aromatic Hydrocarbons. Nature 191, 808–809 (1961). https://doi.org/10.1038/191808a0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/191808a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing