Oxidations of cyclopropane, methylcyclopropane, and arenes with the mono-oxygenase system from Methylococcus capsulatus

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 10, 1981, Pages 482-483

  Dalton, Howard ^a   Golding, Bernard T ^a   Waters, Barry W ^c   Higgins, Raymond ^b   Taylor, John A ^b  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049106234     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39810000482     Document Type: Article

References (14)

1. J. Colby, D. I. Stirling, and H. Dalton, Biochem. J., 1977, 165, 395.
2. J. Colby and H. Dalton, Biochem. J., 1978, 171, 461.
3. C. H. Depuy, G. M. Dappen, K. L. Eilers, and R. A. Klein, J. Org. Chem., 1964, 29, 2813.
4. C. H. Depuy, Acc. Chem. Res., 1968, 1, 33.
5. J. Ooyama and J. W. Foster, Antonie van Leeuwenhoek; J. Microbiol. Serol., 1965, 31, 45.
6. J. W. Daly, D. M. Jerina, and B. Witkop, Experientia, 1972, 28, 1129.
7. For recent mechanistic discussions of oxygenases see J. T. Groves, G. A. McClusky, R. E. White, and M. J. Coon, Biochem. Biophys. Res. Commun., 1978, 81, 154
8. J. T. Groves, Adv. Inorg. Biochem., 1979, 1, 119
9. S. W. May, S. L. Gordon, and M. S. Steltenkamp, J. Am. Chem. Soc., 1977, 99, 2017
10. A. T. Pudzianowski and G. H. Loew, J. Am. Chem. Soc., 1980, 102, 5443.
11. The ease of ring-opening of cyclopropyl to allyl is carbocation carbanion - radical (P. Merlet, S. D. Peyerimhoff, R. J. Buenker, and S. Shih, J. Am. Chem. Soc., 1974, 96, 959).
12. -1 at 25 °C (B. Maillard, D. Forrest, and K. U. Ingold, J. Am. Chem. Soc., 1976, 98, 7024).
13. Groves et al., have very recently suggested a mechanism involving a caged radical intermediate for the oxidation of 1, 2-dideuteriocyclohexene effected by cumene hydroperoxide-cytochrome P450, which gives dideuteriocyclohex-2-en-l-ols indicative of partial allylic rearrangement: J. T. Groves, O. F. Akinbote, and G. E. Avaria, Microsomes Drug Oxid., Chem. Carcinog. (Fourth Int. Symp. Microsomes Drug Oxid.), 1979, ed. M. J. Coon, A. H. Conney, and R. W. Estabrook, Academic Press, New York, 1980, vol. 1, p. 253
14. D. W. Potter and D. J. Reed, J. Am. Chem. Soc., p. 371.