Abstract
The possible involvement of radical cations in enzymatic oxidations is a problem of current interest. A simple approach to address this problem is that of investigating suitable substrates which when converted into radical cations produce a products pattern completely different from that expected when other mechanisms, i.e. involving atom transfer or ionic steps, take place.’ In the last few years we have applied this approach to the study of the mechanism of the side-chain hydroxylation of alkylaromatics by cytochrome P-450 and of the sulfoxidation of aromatic sulfides by cytochrome P-450 and peroxidases. The most recent results of this study will be described in this paper.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Baciocchi, E. (1995) Xenobiotica 25, 653–666.
Groves, T.T., McClusky, G.A., White, R.E., Coon, M.J. (1978). Biochem. Biophys. Research Commun. 81, 154–160; Ortiz de Montellano, P.R. Ed. (1986) Cytochrome P-450, Plenum Press, New York.
Newcomb, M., Le Tadic-Biadatti, M.-H., Chestney, D.L., Roberts, E.S., Hollenberg, P.F. (1995) J. Am. Chem. Soc. 117 12085–12091.
Macdonald, T.L., Gutheim, W.G., Martin, R.B., Guengerich, F.P. (1989) Biochemistry 28, 2071–2077.
An ET mechanism has been suggested for the oxidations of alkylaromatict induced by Mortierella Isabellina. The enzyme which performs these reactions has the characteristics of a cytochrome P-450 monooxygenase. See: Holland, H.L., Kindermann, K., Kumaresan, S., Stefanac, T. (1993) Tetrahedron Asymmetry 4 1353–1364 and references therein.
Amodeo, R., Baciocchi, E., Crescenzi, M., Lanzalunga, O. (1990) Tetrahedron Lett. 25, 3477–3480.
Baciocchi, E., Crescenzi, M., Lanzalunga, 0. (1990) J. Chem. Soc., Chem. Commun. 687–688.
Baciocchi, E., Lanzalunga, 0. unpublished results.
Trahanovsky, W.S., Cramer, J. (1971) 1 Org. Chem. 36 1890–1893; Snook, M.E., Hamilton, G.A. (1974) J. Am. Chem. Soc. 96 860–869.
Eberson, L. (1983) J. Am. Chem. Soc. 105, 3192–3199; Baciocchi, E. Crescenzi, M., Fasella, E. Mattioli, M. (1992) J. Org. Chem. 57, 4684–4689.
Baciocchi, E., Belvedere, S., Bietti, M., Lanzalunga, O. unpublished results.
Baciocchi, E., Mattioli, M., Romano, R., Ruzziconi, R. (1991) 1 Org. Chem. 56 7154–7160.
Baciocchi, E., Bietti, M., Steenken, S. unpublished results.
Watanabe, Y., Iyanagi, T., Oae, S. (1980) Tetrahedron Lett. 21, 3685–3688.
Watanabe, Y., Numata, T. Iyanagi, T. Oae, S. (1981) Bull. Chem. Soc. Jpn. 54, 1163–1170.
Watanabe, Y., Oae, S., Iyanagi, T. (1982) Bull. Chem. Soc. Jpn. 55 188195.
Baciocchi, E., Lanzalunga, O., Marconi, F. (1994) Tetrahedron Lett. 35, 9771–9774.
Baciocchi, E., Lanzalunga, O. unpublished results. See also Cashman, J. R., Proudfoot, J., Ho, Y., Chin, M. S., Olsen, L. D. (1989) 1 Am. Chem. Soc. 111, 4844–4852; Cashman, J. R., Olsen, L. D., Bornheim, L. M. (1990) 1. Am. Chem. Soc. 112, 3191–3195; Cashman, J. R., Olsen, L. D. (1990) Mol. Pharmacol. 38, 573–585.
Dunford, H.B. (1995) Xenobiotica 25, 725–733.
Guengerich, F.P. (1990) Crit. Rev. Biochem. Mol. Biol. 25, 97–153.
Dunford, H.B. (1991) in J. Everse, K.E. Everse, M.B. Grisham (eds.), Peroxidases in Chemistry and Biology, CRC Press, Inc., Boca Raton, pp 2–24.
Kobayashi, S., Nakano, M., Goto, T., Kimura, T., Schaap, A. P. (1986) Biochem. Biophys. Res. Commun. 135, 166–171.
Kobayashi, S., Nakano, M., Kimura, T., Schaap, A. P. (1987) Biochemistry 26, 5019–5022.
Doerge, D. R. (1986)Arch. Biochem. Biophys. 244 678–685.
Doerge, D. R., Cooray, N. M., Brewster, M. E. (1991) Biochemistry 30, 8960–8964.
Harris, R. Z., Newmyer, S. L., Ortiz de Montellano, P. R. (1993) J. Biol. Chem. 268 1637–1645.
Ozaki, S.-I., Ortiz de Montellano, P. R. (1994) 1. Am. Chem. Soc. 116, 44874488; Ozaki, S.-I., Ortiz de Montellano, P. R. (1995) J. Am. Chem. Soc. 117, 7056–7064.
Perez, U., Dunford, H. B. (1990) Biochem. Biophys. Acta 1038, 98–104.
Colonna, S. Gaggero, N., Carrea, G., Pasta, P. (1992) J. Chem. Soc. Chem. Commun. 357–358.
Baciocchi, E., Lanzalunga, O., unpublished results.
Baciocchi, E., Ioele, M., Malandrucco, S., Lanzalunga, O. Steenken, S. J. Am. Chem. Soc., in press.
Zaks, A., Dodds, D.R. (1995) J. Am. Chem. Soc. 117 10419–10424.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Baciocchi, E., Bietti, M., Ioele, M., Lanzalunga, O., Steenken, S. (1997). Mechanisms of the Oxidation of Alkylaromatics and Aromatic Sulfides by Cytochrome P-450 and Peroxidases. In: Minisci, F. (eds) Free Radicals in Biology and Environment. NATO ASI Series, vol 27. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-1607-9_8
Download citation
DOI: https://doi.org/10.1007/978-94-017-1607-9_8
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-4831-8
Online ISBN: 978-94-017-1607-9
eBook Packages: Springer Book Archive