Probing the chemical steps of nitroalkane oxidation catalyzed by 2-nitropropane dioxygenase with solvent viscosity, pH, and substrate kinetic isotope effects

Biochemistry

Volumn 45, Issue 46, 2006, Pages 13889-13898

  Francis, Kevin ^a   Gadda, Giovanni ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DENITRIFICATION; OXIDATION; PH EFFECTS; SUBSTRATES; VISCOSITY;

KINETIC ISOTOPE EFFECTS; NITROALKANES; OXIDATIVE DENITRIFICATION; PH DEPENDENCE;

ENZYME KINETICS;

2 NITROPROPANE; 2 NITROPROPANE DIOXYGENASE; 3 NITROBENZOIC ACID; ETHYLNITRONATE; NITROALKANE; NITROETHANE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; ENZYME METABOLISM; OXIDATION; PH; PRIORITY JOURNAL; VISCOSITY;

ALKANES; CATALYSIS; DIOXYGENASES; HYDROGEN-ION CONCENTRATION; ISOTOPES; KINETICS; MOLECULAR PROBES; OXIDATION-REDUCTION; SOLVENTS; VISCOSITY;

EID: 33751210130     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi060566l     Document Type: Article

References (31)

1. Francis, K., Russell, B., and Gadda, G. (2005) Involvement of a flavosemiquinone in the enzymatic oxidation of nitroalkanes catalyzed by 2-nitropropane dioxygenase, J. Biol. Chem. 280, 5195-5204.
2. Porter, D. J., Voet, J. G., and Bright, H. J. (1973) Direct evidence for carbanions and covalent N(5)-flavin-carbanion adducts as catalytic intermediates in the oxidation of nitroethane by D-amino acid oxidase, J. Biol. Chem. 248, 4400-4416.
3. Porter, D. J., and Bright, H. J. (1983) The mechanism of oxidation of nitroalkanes by horseradish peroxidase, J. Biol. Chem. 258, 9913-9924.
4. Porter, D. J., and Bright, H. J. (1977) Mechanism of oxidation of nitroethane by glucose oxidase, J. Biol. Chem. 252, 4361-4370.
5. 2, J. Biol. Chem. 262, 14428-14434.
6. Gadda, G., and Fitzpatrick, P. F. (1999) Substrate specificity of a nitroalkane-oxidizing enzyme, Arch. Biochem. Biophys. 363, 309-313.
7. Gorlatova, N., Tchorzewski, M., Kurihara, T., Soda, K., and Esaki, N. (1998) Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa, Appl. Environ. Microbiol. 64, 1029-1033.
8. Hanessian, S., and Pham, V. (2000) Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones, Org. Lett. 2, 2975-2978.
9. Ballini, R., Barboni, L., and Giarlo, G. (2003) Nitroalkanes in aqueous medium as an efficient and eco-friendly source for the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans, J. Org. Chem. 68, 9173-9176.
10. Fiala, E. S., Czerniak, R., Castonguay, A., Conaway, C. C., and Rivenson, A. (1987) Assay of 1-nitropropane, 2-nitropropane, 1-azoxypropane and 2-azoxypropane for carcinogenicity by gavage in Sprague-Dawley rats, Carcinogenesis 8, 1947-1949.
11. Conaway, C. C., Nie, G., Hussain, N. S., and Fiala, E. S. (1991) Comparison of oxidative damage to rat liver DNA and RNA by primary nitroalkanes, secondary nitroalkanes, cyclopentanone oxime, and related compounds, Cancer Res. 51, 3143-3147.
12. Dayal, R., Gescher, A., Harpur, E. S., Pratt, I., and Chipman, J. K. (1989) Comparison of the hepatotoxicity in mice and the mutagenicity of three nitroalkanes, Fundam. Appl. Toxicol. 13, 341-348.
13. Lewis, T. R., Ulrich, C. E., and Busey, W. M. (1979) Subchronic inhalation toxicity of nitromethane and 2-nitropropane. J. Environ. Pathol. Toxicol. 2, 233-249.
14. Haas-Jobelius, M., Coulston, F., and Korte, F. (1992) Effects of short-term inhalation exposure to 1-nitropropane and 2-nitropropane on rat liver enzymes, Ecotoxicol. Environ. Saf. 23, 253-259.
15. Sakano, K., Oikawa, S., Murata, M., Hiraku, Y., Kojima, N., and Kawanishi, S. (2001) Mechanism of metal-mediated DNA damage induced by metabolites of carcinogenic 2-nitropropane, Mutat. Res. 479, 101-111.
16. Ha, J. Y., Min, J. Y., Lee, S. K., Kim, H. S., Kim do, J., Kim, K. H., Lee, H. H., Kim, H. K., Yoon, H. J., and Suh, S. W. (2006) Crystal structure of 2-nitropropane dioxygenase complexed with FMN and substrate. Identification of the catalytic base, J. Biol. Chem. 281, 18660-18667.
17. Allison, R. D., and Purich, D. L. (1979) Practical considerations in the design of initial velocity enzyme rate assays, Methods Enzymol. 63, 3-22.
18. Lide, D. R. (2000) Handbook of Chemistry and Physics, 6th ed., Vol. 2000-2001, CRC Press, Boca Raton, FL.
19. Gadda, G., and Fitzpatrick, P. F. (2000) Mechanism of nitroalkane oxidase: 2. pH and kinetic isotope effects, Biochemistry 39, 1406-1410.
20. Cleland, W. W. (1982) The use of pH studies to determine chemical mechanisms of enzyme-catalyzed reactions, Methods Enzymol. 87, 390-405.
21. Cleland, W. W. (1975) Partition analysis and the concept of net rate constants as tools in enzyme kinetics, Biochemistry 14, 3220-3224.
22. Meah, Y., and Massey, V. (2000) Old yellow enzyme: Stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization, Proc. Natl. Acad. Sci. U.S.A. 97, 10733-10738.
23. Gadda, G., Choe, D. Y., and Fitzpatrick, P. F. (2000) Use of pH and kinetic isotope effects to dissect the effects of substrate size on binding and catalysis by nitroalkane oxidase, Arch. Biochem. Biophys. 382, 138-144.
24. Fitzpatrick, P. F., Orville, A. M., Nagpal, A., and Valley, M. P. (2005) Nitroalkane oxidase, a carbanion-forming flavoprotein homologous to acyl-CoA dehydrogenase, Arch. Biochem. Biophys. 433, 157-165.
25. Nagpal, A., Valley, M. P., Fitzpatrick, P. F., and Orville, A. M. (2006) Crystal structures of nitroalkane oxidase: Insights into the reaction mechanism from a covalent complex of the flavoenzyme trapped during turnover, Biochemistry 45, 1138-1150.
26. Valley, M. P., and Fitzpatrick, P. F. (2003) Inactivation of nitroalkane oxidase upon mutation of the active site base and rescue with a deprotonated substrate, J. Am. Chem. Soc. 125, 8738-8739.
27. Valley, M. P., and Fitzpatrick, P. F. (2003) Reductive half-reaction of nitroalkane oxidase: Effect of mutation of the active site aspartate to glutamate, Biochemistry 42, 5850-5856.
28. Valley, M. P., Tichy, S. E., and Fitzpatrick, P. F. (2005) Establishing the kinetic competency of the cationic imine intermediate in nitroalkane oxidase, J. Am. Chem. Soc. 127, 2062-2066.
29. Gadda, G., and Fitzpatrick, P. F. (2000) Iso-mechanism of nitroalkane oxidase: 1. Inhibition studies and activation by imidazole, Biochemistry 39, 1400-1405.
30. Valley, M. P., and Fitzpatrick, P. F. (2004) Comparison of enzymatic and non-enzymatic nitroethane anion formation: Thermodynamics and contribution of tunneling, J. Am. Chem. Soc. 126, 6244-6245.
31. Nielsen, A. T. (1969) Nitronic acids and esters, in The Chemistry of the Nitro and Nitroso Groups (Feuer, H., Ed.) pp 349-486, Interscience Publishers, New York.