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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, ...

Bertrand, E. et al., Perin, A. et al., Auclair, K. et al., Brazeau, B.J. et al., Moe, L.A. et al., et al.

Newcomb, Shen, Lu, Coon, Hollenberg, Kopp, Lippard,

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Disease relevance of norcarane

2,3-Dihydroxybutyraldehyde at nontoxic doses (500 mg/kg body weight i.p. daily for 7 days) slowed down the growth of solid and ascites tumors in mice [1].
The antitumor activity of 2,3-dihydroxybutyraldehyde on Ehrlich carcinoma, Sarcoma 180, and Yoshida AH 130 hepatoma, as well as the aldehyde dehydrogenase activity in these tumors, was studied [1].
Soluble methane monooxygenase (sMMO) from Methylosinus trichosporium OB3b catalyzes the oxidation of norcarane to afford 3-hydroxymethylcyclohexene and 3-cycloheptenol, compounds characteristic of radical and cationic intermediates, respectively, in addition to 2- and 3-norcaranols [2].
T4MO expressed in E. coli also catalyzes the hydroxylation of norcarane with a radical lifetime of approximately 0.07 ns [3].
The hydroxylation of norcarane yields a distribution of products consistent with an "oxygen-rebound" mechanism for the enzyme in both the wild type Pseudomonas putida GPo1 and AlkB from P. putida GPo1 expressed in Escherichia coli [3].

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

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 [8].

References

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]
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]
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]
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]
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]
endo/exo isomerism in norcarane and 2-norcaranol hydrotrioxides (ROOOH). Erzen, E., Cerkovnik, J., Plesnicar, B. J. Org. Chem. (2003) [Pubmed]
Oxygen-18 tracer studies of enzyme reactions with radical/cation diagnostic probes. Moe, L.A., Fox, B.G. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
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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