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Chemical Compound Review

Norcarane     bicyclo[4.1.0]heptane

Synonyms: AG-E-92027, AG-K-76356, NSC-143399, AC1L1SNA, KB-58728, ...
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Disease relevance of norcarane


High impact information on norcarane

  • Products indicative of a radical intermediate with a lifetime ranging from 16 to 52 ps were detected during the oxidation of norcarane by P450(cam) (CYP101), P450(BM3) (CYP102), CYP2B1, and CYP2E1 [4].
  • Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane [4].
  • The unique implication of a discrete radical intermediate in hydroxylations of norcarane may be the consequence of a minor reaction pathway for the enzymes that is not manifest in reactions with other probes [5].
  • Ozonation of norcarane (1) yielded endo and exo norcarane hydrotrioxides (2a, 2b), as characterized by (1)H and (13)C NMR spectroscopy [6].
  • This review considers reactions of enzymes with the cyclopropanoid radical/cation diagnostic probes norcarane, 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane as elaborated by the use of 18O2 and 18OH2 to trace the origin of O-atoms incorporated during catalysis [7].

Associations of norcarane with other chemical compounds


  1. Carcinostatic effect of aliphatic aldehydes and aldehyde dehydrogenase activity in Ehrlich carcinoma, Sarcoma 180, and Yoshida AH 130 hepatoma. Perin, A., Sessa, A., Ciaranfi, E. Cancer Res. (1978) [Pubmed]
  2. Intermediate Q from soluble methane monooxygenase hydroxylates the mechanistic substrate probe norcarane: evidence for a stepwise reaction. Brazeau, B.J., Austin, R.N., Tarr, C., Groves, J.T., Lipscomb, J.D. J. Am. Chem. Soc. (2001) [Pubmed]
  3. Reaction mechanisms of non-heme diiron hydroxylases characterized in whole cells. Bertrand, E., Sakai, R., Rozhkova-Novosad, E., Moe, L., Fox, B.G., Groves, J.T., Austin, R.N. J. Inorg. Biochem. (2005) [Pubmed]
  4. Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane. Auclair, K., Hu, Z., Little, D.M., Ortiz De Montellano, P.R., Groves, J.T. J. Am. Chem. Soc. (2002) [Pubmed]
  5. Evaluation of norcarane as a probe for radicals in cytochome p450- and soluble methane monooxygenase-catalyzed hydroxylation reactions. Newcomb, M., Shen, R., Lu, Y., Coon, M.J., Hollenberg, P.F., Kopp, D.A., Lippard, S.J. J. Am. Chem. Soc. (2002) [Pubmed]
  6. endo/exo isomerism in norcarane and 2-norcaranol hydrotrioxides (ROOOH). Erzen, E., Cerkovnik, J., Plesnicar, B. J. Org. Chem. (2003) [Pubmed]
  7. Oxygen-18 tracer studies of enzyme reactions with radical/cation diagnostic probes. Moe, L.A., Fox, B.G. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  8. Remarkable aliphatic hydroxylation by the diiron enzyme toluene 4-monooxygenase in reactions with radical or cation diagnostic probes norcarane, 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane. Moe, L.A., Hu, Z., Deng, D., Austin, R.N., Groves, J.T., Fox, B.G. Biochemistry (2004) [Pubmed]
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