Skip to main content
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1983 Nov;80(22):7039–7041. doi: 10.1073/pnas.80.22.7039

Oxygenation of hydrocarbons by cytochrome P-450 model compounds: modification of reactivity by axial ligands.

J P Collman, T Kodadek, S A Raybuck, B Meunier
PMCID: PMC390122  PMID: 6580626

Abstract

The rate of olefin oxygenation catalyzed by synthetic metalloporphyrins is examined, employing sodium hypochlorite as the oxygen atom source. The rate of epoxidation and the stability of the catalyst are shown to be dependent on the nature of the axial ligand employed. A rationale for this effect is presented and analogy is made to the role of the thiolate ligand in cytochrome P-450.

Full text

PDF
7039

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Collman J. P., Gagne R. R., Reed C. A., Halbert T. R., Lang G., Robinson W. T. "Picket fence porphyrins." Synthetic models for oxygen binding hemoproteins. J Am Chem Soc. 1975 Mar 19;97(6):1427–1439. doi: 10.1021/ja00839a026. [DOI] [PubMed] [Google Scholar]
  2. Collman J. P., Sorrell T. N. Letter: A model for the carbonyl adduct of ferrous cytochrome P450. J Am Chem Soc. 1975 Jul 9;97(14):4133–4134. doi: 10.1021/ja00847a046. [DOI] [PubMed] [Google Scholar]
  3. Dawson J. H., Holm R. H., Trudell J. R., Barth G., Linder R. E., Bunnenberg E., Djerassi C., Tang S. C. Letter: Oxidized cytochrome P-450. Magnetic circular dichroism evidence for thiolate ligation in the substrate-bound form. Implications for the catalytic mechanism. J Am Chem Soc. 1976 Jun 9;98(12):3707–3708. doi: 10.1021/ja00428a054. [DOI] [PubMed] [Google Scholar]
  4. Dolphin D., James B. R., Welborn H. C. Proton activities for three states of cytochrome P-450cam. Biochem Biophys Res Commun. 1979 May 28;88(2):415–421. doi: 10.1016/0006-291x(79)92064-3. [DOI] [PubMed] [Google Scholar]
  5. White R. E., Coon M. J. Oxygen activation by cytochrome P-450. Annu Rev Biochem. 1980;49:315–356. doi: 10.1146/annurev.bi.49.070180.001531. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES