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2000 | 47 | 4 | 941-949
Article title

Two-electron reduction of nitroaromatic compounds by Enterobacter cloacae NAD(P)H nitroreductase: Description of quantitative structure-activity relationships.

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Abstracts
EN
Enterobacter cloacae NAD(P)H:nitroreductase catalyzes the reduction of a series of nitroaromatic compounds with steady-state bimolecular rate constants (kcat/Km) ranging from 104 M-1s-1 to 107 M-1s-1 , and oxidizing 2 moles NADH per mole mononitrocompound. Oxidation of excess NADH by polynitrobenzenes including explosives 2,4,6-trinitrotoluene (TNT) and 2,4,6-trinitrophenyl-N-methylnitramine (tetryl), has been observed as a slower secondary process, accompanied by O2 consumption. This type of 'redox cycling' was not related to reactions of nitroaromatic anion-radicals, but was caused by the autoxidation of relatively stable reaction products. The logs kcat/Km of all the compounds examined exhibited parabolic dependence on their enthalpies of single-electron- or two-electron (hydride) reduction, obtained by quantum mechanical calculations. This type of quantitative structure-activity relationships shows that the reactivity of nitroaromatics towards E. cloacae nitroreductase depends mainly on their hydride accepting properties, but not on their particular structure, and does not exclude the possibility of multistep hydride transfer.
Keywords
Publisher

Year
Volume
47
Issue
4
Pages
941-949
Physical description
Dates
published
2000
received
2000-10-3
accepted
2000-11-7
Contributors
  • Institute of Biochemistry, Mokslininku 12, Vilnius 2600, Lithuania
  • Department of Chemistry, University of Kentucky, 106 Chemistry-Physics Building, Lexington, KY 40506-0055, U.S.A.
  • Institute of Biochemistry, Mokslininku 12, Vilnius 2600, Lithuania
  • Institute of Biochemistry, Mokslininku 12, Vilnius 2600, Lithuania
  • Department of Chemistry, University of Kentucky, 106 Chemistry-Physics Building, Lexington, KY 40506-0055, U.S.A.
  • Institute of Biochemistry, Mokslininku 12, Vilnius 2600, Lithuania
References
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Document Type
Publication order reference
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YADDA identifier
bwmeta1.element.bwnjournal-article-abpv47i4p941kz
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