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Literature summary for 1.6.5.5 extracted from

  • Valiauga, B.; Williams, E.M.; Ackerley, D.F.; Cenas, N.
    Reduction of quinones and nitroaromatic compounds by Escherichia coli nitroreductase A (NfsA) Characterization of kinetics and substrate specificity (2017), Arch. Biochem. Biophys., 614, 14-22 .
    View publication on PubMed
Search for more literature for 1.6.5.5

Application

Application Comment Organism
environmental protection NfsA has potential applications in the biodegradation of nitroaromatic environment pollutants, e.g. explosives Escherichia coli
medicine NfsA has potential applications in the anticancer strategy gene-directed enzyme prodrug therapy Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
dicoumarol
-
 Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information Michaelis-Menten steady-state kinetics. For NfsA the oxidative half-reaction (i.e., the reoxidation of FMNHby the oxidant substrate) is a rate-limiting step, because the values of kcat at infinite concentrations of tetryl or 2,4,6-trinitrotoluene are substantially lower than the lowest rate of the reductive half reaction (the reduction of FMN by NADPH) measured in the preliminary rapid reaction experiments. Stopped-flow and single-turnover measurements. The flavoenzymes reducing quinones in a two-electron way possess a highly unstable semiquinone state, i.e., the redox potential of flavin semiquinone/dihydroflavin couple is more positive than the potential of flavin/semiquinone couple, thermodynamics, overview Escherichia coli
0.0009
-
 5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
0.0016
-
 5-hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
0.0064
-
 2-hydroxy-3-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
0.0066
-
 2-Hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
0.007
-
 1,4-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
0.008
-
 2-methyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
0.011
-
 1,4-benzoquinone pH 7.0, 25°C Escherichia coli
0.012
-
 9,10-phenanthrenequinone pH 7.0, 25°C Escherichia coli
0.015
-
 1,8-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
0.016
-
 riboflavin pH 7.0, 25°C Escherichia coli
0.016
-
 2,6-dimethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
0.022
-
 2,3-dichloro-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
0.033
-
 1,4-Naphthoquinone pH 7.0, 25°C Escherichia coli
0.074
-
 9,10-anthraquinone-2-sulfonic acid pH 7.0, 25°C Escherichia coli
0.13
-
 2-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
1.1
-
 tetramethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Reaction

Reaction Comment Organism Reaction ID
NADPH + H+ + 2 quinone = NADP+ + 2 semiquinone catalytic mechanism analysis, two (four)-electron reduction of nitrobenzenes and single-step (H-) hydride transfer mechanism. NfsA follows a ping-pong mechanism, overview Escherichia coli
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,4-benzoquinone + NADPH + H+
-
 Escherichia coli 1,4-benzoquinol + NADP+
-
 ?
1,4-dihydroxy-9,10-anthraquinone + NADPH + H+
-
 Escherichia coli anthracene-1,4,9,10-tetrol + NADP+
-
 ?
1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 1,4-naphthoquinol + NADP+
-
 ?
1,8-dihydroxy-9,10-anthraquinone + NADPH + H+
-
 Escherichia coli anthracene-1,8,9,10-tetrol + NADP+
-
 ?
2,3-dichloro-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 2,3-dichloro-1,4-naphthoquinol + NADP+
-
 ?
2,6-dimethyl-1,4-benzoquinone + NADPH + H+
-
 Escherichia coli 2,6-dimethyl-1,4-benzoquinol + NADP+
-
 ?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli naphthalene-1,2,4-triol + NADP+
-
 ?
2-hydroxy-3-methyl-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 3-methylnaphthalene-1,2,4-triol + NADP+
-
 ?
2-methyl-1,4-benzoquinone + NADPH + H+
-
 Escherichia coli 2-methyl-1,4-benzoquinol + NADP+
-
 ?
2-methyl-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 2-methyl-1,4-naphthoquinol + NADP+
-
 ?
5,8-dihydroxy-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 5,8-dihydroxy-1,4-naphthoquinol + NADP+
-
 ?
5-hydroxy-1,4-naphthoquinone + NADPH + H+
-
 Escherichia coli 5-hydroxy-1,4-naphthoquinol + NADP+
-
 ?
9,10-anthraquinone-2-sulfonic acid + NADPH + H+
-
 Escherichia coli 9,10-anthraquinol-2-sulfonic acid + NADP+
-
 ?
9,10-phenanthrenequinone + NADPH + H+
-
 Escherichia coli 9,10-phenanthrenequinol + NADP+
-
 ?
additional information NADPH-dependent reduction of quinones and nitroaromatic compounds by NfsA, overview. The reactivity of nitroaromatic compounds (log kcat/Km) follows a linear dependence on their single-electron reduction potential, indicating a limited role for compound structure or active site flexibility in their reactivity. The reactivity of quinones is lower than that of nitroaromatics having similar single-electron reduction potential values, except for the significantly enhanced reactivity of 2-OH-1,4-naphthoquinones. The reduction of quinones by NfsA is most consistent with a single-step (H-) hydride transfer mechanism, quantitative analysis of two-electron reduction of quinones and nitroaromatics, overview Escherichia coli ?
-
 ?
riboflavin + NADPH + H+
-
 Escherichia coli ? + NADP+
-
 ?
tetramethyl-1,4-benzoquinone + NADPH + H+
-
 Escherichia coli tetramethyl-1,4-benzoquinol + NADP+
-
 ?

Synonyms

Synonyms Comment Organism
NfsA
-
 Escherichia coli
nitroreductase A
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Escherichia coli

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.7
-
 1,4-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
1.4
-
 9,10-anthraquinone-2-sulfonic acid pH 7.0, 25°C Escherichia coli
1.6
-
 1,8-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
2.5
-
 tetramethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
3 6 2-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
4.2
-
 riboflavin pH 7.0, 25°C Escherichia coli
12
-
 5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
22
-
 5-hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
46
-
 1,4-Naphthoquinone pH 7.0, 25°C Escherichia coli
51
-
 2,6-dimethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
54
-
 9,10-phenanthrenequinone pH 7.0, 25°C Escherichia coli
54
-
 2-methyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
56
-
 2-hydroxy-3-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
61
-
 2,3-dichloro-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
62
-
 1,4-benzoquinone pH 7.0, 25°C Escherichia coli
72
-
 2-Hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
 assay at Escherichia coli

Cofactor

Cofactor Comment Organism Structure
FMN prosthetic group involved in the reaction Escherichia coli
NADPH
-
 Escherichia coli

General Information

General Information Comment Organism
additional information comparisons of the quantitative structure-activity relationships of single-electron reduction of quinones and nitroaromatic compounds by dehydrogenase (electron transferase) flavoenzymes, overview Escherichia coli
physiological function NfsA has potential applications in the biodegradation of nitroaromatic environment pollutants, e.g. explosives, and is also of interest for the anticancer strategy gene-directed enzyme prodrug therapy Escherichia coli

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.7
-
 tetramethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
18.9
-
 9,10-anthraquinone-2-sulfonic acid pH 7.0, 25°C Escherichia coli
100
-
 1,4-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
106.7
-
 1,8-dihydroxy-9,10-anthraquinone pH 7.0, 25°C Escherichia coli
262.5
-
 riboflavin pH 7.0, 25°C Escherichia coli
276.9
-
 2-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
1393.9
-
 1,4-Naphthoquinone pH 7.0, 25°C Escherichia coli
2772.7
-
 2,3-dichloro-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
3187.5
-
 2,6-dimethyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
5636.4
-
 1,4-benzoquinone pH 7.0, 25°C Escherichia coli
6750
-
 2-methyl-1,4-benzoquinone pH 7.0, 25°C Escherichia coli
8750
-
 2-hydroxy-3-methyl-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
10909.1
-
 2-Hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
13333
-
 5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli
13750
-
 5-hydroxy-1,4-naphthoquinone pH 7.0, 25°C Escherichia coli