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Information on EC 1.7.1.B3 - aromatic nitroreductase [NADPH] and Organism(s) Escherichia coli and UniProt Accession P17117

for references in articles please use BRENDA:EC1.7.1.B3
preliminary BRENDA-supplied EC number
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Escherichia coli
UNIPROT: P17117 not found.
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Word Map
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  • 1.7.1.B3
  • hypoplasia
  • dermal
  • x-linked
  • goltz
  • ectodermal
  • malformation
  • ocular
  • porcupine
  • mesoderm
  • blaschko
  • skew
  • x-chromosome
  • postzygotic
  • teeth
  • goltz-gorlin
  • multisystemic
  • herniation
  • diaphragmatic
  • x-inactivation
  • angioma
  • papillomas
  • hernia
  • wingless
  • cutis
  • nail
  • o-acyltransferase
  • aplasia
  • patchy
  • environmental protection
  • medicine
The taxonomic range for the selected organisms is: Escherichia coli
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
an aromatic amine
+
3
NADP+
+
2
H2O
=
an aromatic nitrate
+
3
NADPH
+
3
H+
+
3
+
2
=
+
3
+
3
Synonyms
nitrofurazone reductase, oxygen-insensitive nad(p)h:nitroreductases, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nitrofurazone reductase
-
nitroreductase A
-
nitroreductase A
-
-
oxygen-insensitive NAD(P)H:nitroreductases
-
-
oxygen-insensitive nitroreductase (NADPH)
-
-
-
-
additional information
-
cf. EC 1.6.5.5
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an aromatic amine + 3 NADP+ + 2 H2O = an aromatic nitrate + 3 NADPH + 3 H+
show the reaction diagram
the enzyme uses NADPH as the hydrogen donor to catalyze the reduction of a nitro group by a ping-pong Bi-Bi kinetic mechanism
an aromatic amine + 3 NADP+ + 2 H2O = an aromatic nitrate + 3 NADPH + 3 H+
show the reaction diagram
catalytic mechanism analysis, two (four)-electron reduction of nitrobenzenes and single-step (H-) hydride transfer mechanism. NfsA follows a ping-pong mechanism, overview
-
SYSTEMATIC NAME
IUBMB Comments
aromatic nitrate:NADPH oxidroreductase
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxylamino-2,6-dinitrotoluene + NADP+ + H2O
show the reaction diagram
2,4,6-trinitrotoluene + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
2,4-dinitrotoluene + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
2-amino-4,6-dinitrotoluene + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
4-amino-2,6-dinitrotoluene + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NADPH + H+
? + NADP+
show the reaction diagram
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
-
-
?
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
show the reaction diagram
a nitro-CBI prodrug, low activity
-
-
?
nitrofurazone + NADPH + H+
5-(hydroxyamino)furan-2-carbaldehyde semicarbazone + NADP+ + H2O
show the reaction diagram
-
-
-
?
2,4,6-trinitrophenyl N-methylnitramine + 4 NADPH + H+
?
show the reaction diagram
-
-
-
-
?
2,4,6-trinitrotoluene + 2 NADPH + H+
?
show the reaction diagram
-
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-nitroacetophenone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
4-nitrobenzoic acid + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NADPH + H+
? + NADP+
show the reaction diagram
-
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
-
-
?
m-dinitrobenzene + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
nifuroxime + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
nitrobenzene + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
nitrobenzene + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
nitrofurantoin + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
o-dinitrobenzene + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
p-dinitrobenzene + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
p-nitroacetophenone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
p-nitrobenzaldehyde + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
p-nitrobenzoic acid + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
tetryl + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxylamino-2,6-dinitrotoluene + NADP+ + H2O
show the reaction diagram
-
-
-
?
2,4,6-trinitrophenyl N-methylnitramine + 4 NADPH + H+
?
show the reaction diagram
-
-
-
-
?
2,4,6-trinitrotoluene + 2 NADPH + H+
?
show the reaction diagram
-
-
-
-
?
4-nitroacetophenone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
4-nitrobenzoic acid + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
nitrobenzene + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FMN
a flavoenzyme which contains FMN as the prosthetic group
FMN
-
prosthetic group involved in the reaction
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
-
-
dicoumarol
-
inhibits Escherichia coli enzyme NfsB far more strongly than enzyme NfsA, by acting as a competitive inhibitor towards NADPH, uncompetitive towards substrate tetryl
NADP+
-
inhibition of NfsA-catalyzed tetryl reduction by NADP+
additional information
the enzyme is O2-insensitive
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.013 - 0.029
2,4,6-trinitrotoluene
0.176 - 0.366
2,4-dinitrotoluene
0.3257
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
0.6427
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
0.322 - 0.487
5-(aziridin-1-yl)-2,4-dinitrobenzamide
0.049 - 0.085
NADPH
0.012 - 0.064
nitrofurazone
0.033
2,4,6-trinitrotoluene
-
pH 7.0, 25°C
0.23
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
pH 7.0, 25°C
0.046
m-dinitrobenzene
-
pH 7.0, 25°C
0.031
nifuroxime
-
pH 7.0, 25°C
1.5
nitrobenzene
-
pH 7.0, 25°C
0.019
Nitrofurantoin
-
pH 7.0, 25°C
0.018
o-dinitrobenzene
-
pH 7.0, 25°C
0.037
p-dinitrobenzene
-
pH 7.0, 25°C
0.39
p-nitroacetophenone
-
pH 7.0, 25°C
0.17
p-nitrobenzaldehyde
-
pH 7.0, 25°C
2.5
p-nitrobenzoic acid
-
pH 7.0, 25°C
0.011
tetryl
-
pH 7.0, 25°C
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.67 - 56.21
2,4,6-trinitrotoluene
0.7 - 24.94
2,4-dinitrotoluene
12.36
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
1.05
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
1.08 - 36.64
5-(aziridin-1-yl)-2,4-dinitrobenzamide
0.46 - 16.3
NADPH
0.8 - 19.37
nitrofurazone
110
2,4,6-trinitrophenyl N-methylnitramine
-
at pH 7.0 and 25°C
-
89 - 135.1
2,4,6-trinitrotoluene
59.4
4-Nitroacetophenone
-
at pH 7.0 and 25°C
64.3
4-nitrobenzoic acid
-
at pH 7.0 and 25°C
15
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
pH 7.0, 25°C
55
m-dinitrobenzene
-
pH 7.0, 25°C
180
nifuroxime
-
pH 7.0, 25°C
14 - 14.2
nitrobenzene
136
Nitrofurantoin
-
pH 7.0, 25°C
60
o-dinitrobenzene
-
pH 7.0, 25°C
27
p-dinitrobenzene
-
pH 7.0, 25°C
59
p-nitroacetophenone
-
pH 7.0, 25°C
30
p-nitrobenzaldehyde
-
pH 7.0, 25°C
64
p-nitrobenzoic acid
-
pH 7.0, 25°C
85
tetryl
-
pH 7.0, 25°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
50 - 1940
2,4,6-trinitrotoluene
2 - 142
2,4-dinitrotoluene
38
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
1.6
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged enzyme
2 - 112
5-(aziridin-1-yl)-2,4-dinitrobenzamide
5 - 191.7
NADPH
10 - 1610
nitrofurazone
7900
2,4,6-trinitrophenyl N-methylnitramine
-
at pH 7.0 and 25°C
-
2697 - 2700
2,4,6-trinitrotoluene
150
4-Nitroacetophenone
-
at pH 7.0 and 25°C
2.5
4-nitrobenzoic acid
-
at pH 7.0 and 25°C
65.2
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
pH 7.0, 25°C
1195.7
m-dinitrobenzene
-
pH 7.0, 25°C
5806.5
nifuroxime
-
pH 7.0, 25°C
1.5 - 9.3
nitrobenzene
7157.9
Nitrofurantoin
-
pH 7.0, 25°C
3333.3
o-dinitrobenzene
-
pH 7.0, 25°C
729.7
p-dinitrobenzene
-
pH 7.0, 25°C
151.3
p-nitroacetophenone
-
pH 7.0, 25°C
176.5
p-nitrobenzaldehyde
-
pH 7.0, 25°C
25.6
p-nitrobenzoic acid
-
pH 7.0, 25°C
7727.27
tetryl
-
pH 7.0, 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018
dicoumarol
-
pH 7.0, 25°C
additional information
additional information
-
inhibition kinetics
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.1
purified recombinant mutant F46A, pH 7.0, 22°C, substrate nitrofurazone
0.29
purified recombinant mutant F46N, pH 7.0, 22°C, substrate nitrofurazone
3.74
purified recombinant mutant F46Y, pH 7.0, 22°C, substrate nitrofurazone
7.75
purified recombinant wild-type enzyme, pH 7.0, 22°C, substrate nitrofurazone
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
assay at room temperature
25
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
nitroreductases are a family of flavoproteins that catalyze the NAD(P)H-dependent reduction of nitro groups to hydroxylamino and/or amino groups on various nitro-substituted compounds
physiological function
residue Phe42 is critical for the catalytic activity of Escherichia coli major nitroreductase NfsA, Phe42 is important for maintaining NfsA activity and structure
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
additional information
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F42A
site-directed mutagenesis, the mutant enzymes shows 99% reduced activity toward nitrofurazone compared to the wild-type, and loss of helix content
F42N
site-directed mutagenesis, the mutant enzymes shows 96% reduced activity toward nitrofurazone compared to the wild-type, and loss of helix content
F42Y
site-directed mutagenesis, the mutant enzymes shows 52% reduced activity toward nitrofurazone compared to the wild-type
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
the enzyme is O2-insensitive
742167
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged wild-type and mutant enzymes from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
recombinant N-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography to over 95% purity
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene nfsA, recombinant expression of His6-tagged wild-type and mutant enzymes in Escherichia coli strain BL21(DE3), subcloning in Escherichia coli strain DH5alpha
gene nfsA, recombinant expression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)
gene nfsA, recombinant overexpression in Escherichia coli reporter strain SOS-R2, which contains a lacZ reporter gene under control of the SOS responsive promoter sfiA, functional nitroreductase NfsA expression in human HCT-116 cells
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
environmental protection
-
NfsA has potential applications in the biodegradation of nitroaromatic environment pollutants, e.g. explosives
medicine
-
NfsA has potential applications in the anticancer strategy gene-directed enzyme prodrug therapy
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Arch. Biochem. Biophys.
614
14-22
2017
Escherichia coli
Manually annotated by BRENDA team
Yang, J.; Zhan, J.; Bai, J.; Liu, P.; Xue, Y.; Yang, Q.
Residue Phe42 is critical for the catalytic activity of Escherichia coli major nitroreductase NfsA
Biotechnol. Lett.
35
1693-1700
2013
Escherichia coli (P17117)
Manually annotated by BRENDA team
Green, L.K.; Syddall, S.P.; Carlin, K.M.; Bell, G.D.; Guise, C.P.; Mowday, A.M.; Hay, M.P.; Smaill, J.B.; Patterson, A.V.; Ackerley, D.F.
Pseudomonas aeruginosa NfsB and nitro-CBI-DEI - a promising enzyme/prodrug combination for gene directed enzyme prodrug therapy
Mol. Cancer
12
58
2013
Escherichia coli (P17117)
Manually annotated by BRENDA team
Bai, J.; Yang, J.; Liu, P.; Yang, Q.
Transformation pathway of 2,4,6-trinitrotoluene by Escherichia coli nitroreductases and improvement of activity using structure-based mutagenesis
Process Biochem.
50
705-711
2015
Escherichia coli (P17117)
Manually annotated by BRENDA team
Valiauga, B.; Miseviciene, L.; Rich, M.H.; Ackerley, D.F.; Sarlauskas, J.; Cenas, N.
Mechanism of two-/four-electron reduction of nitroaromatics by oxygen-insensitive nitroreductases the role of a non-enzymatic reduction step
Molecules
23
1672
2018
Escherichia coli
Manually annotated by BRENDA team