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Induced Nucleophilic Substitution in Benzo[a]pyrene

Nature volume 241, pages 271–272 (1973)Cite this article

Abstract

Cavalieri and Calvin have proposed1,2 that the carcinogenic action of benzo[a]pyrene (BaP) may arise from aryl hydroxylase induced binding to nucleophilic cellular components. Their theory proposes that attack by electrophilic oxygen, produced in the hydroxylase system, occurs at the 6 position of the hydrocarbon to give a carbonium ion, localized primarily at the 1 and 3 positions, which can undergo attack with nucleophilic cellular components. Alternatively, initial attack could occur at 1 or 3, followed by nucleophilic reaction at 6.

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References

  1. Cavalieri, E., and Calvin, M., Proc. US Nat. Acad. Sci., 68, 1251 (1971).

    Article  ADS  CAS  Google Scholar 

  2. Cavalieri, E., and Calvin, M., Photochem. Photobiol., 14, 641 (1971).

    Article  CAS  Google Scholar 

  3. Rochlitz, J., Tetrahedron, 23, 3048 (1967).

    Article  Google Scholar 

  4. Buu-Hoi, N. P., and Lavit, D., Tetrahedron, 8, 1 (1960).

    Article  CAS  Google Scholar 

  5. Tye, R., Graf, M. J., and Horton, A. W., Anal. Chem., 27, 248 (1955).

    Article  CAS  Google Scholar 

  6. Bartelle, K. D., Jones, D. W., and Matthews, R. S., Spectrochim. Acta, 25, A, 1603 (1969).

    Article  Google Scholar 

  7. Haigh, C. W., and Mallion, R. B., J. Mol. Spec., 29, 418 (1969).

    Article  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Chemical Biodynamics, University of California, Berkeley, California, 94720

    M. D. JOHNSON & M. CALVIN

Authors
  1. M. D. JOHNSON
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  2. M. CALVIN
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JOHNSON, M., CALVIN, M. Induced Nucleophilic Substitution in Benzo[a]pyrene. Nature 241, 271–272 (1973). https://doi.org/10.1038/241271b0

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  • DOI: https://doi.org/10.1038/241271b0

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