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1.14.12.23: nitroarene dioxygenase

This is an abbreviated version!
For detailed information about nitroarene dioxygenase, go to the full flat file.

Word Map on EC 1.14.12.23

Reaction

nitrobenzene
+
NADH
+
O2
=
catechol
+
nitrite
+
NAD+

Synonyms

2-chloronitrobenzene dioxygenase, 2NTDO, cnbA, cnbAa, cnbAb, cnbAc, cnbAd, MntAa, MntAb, MntAc, MntAd, naphthalene dioxygenase, nbzAa, nbzAb, nbzAc, nbzAd

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.12 With NADH or NADPH as one donor, and incorporation of two atoms of oxygen into the other donor
                1.14.12.23 nitroarene dioxygenase

Engineering

Engineering on EC 1.14.12.23 - nitroarene dioxygenase

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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A405G
-
synthesizes 17% 3-methylcatechol, 83% 4-methylcatechol from substrate 3-nitrotoluene
I204A
-
synthesizes 2% 3-methylcatechol, 97% 4-methylcatechol and 1% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
I204T
-
synthesizes 5% 3-methylcatechol, 93% 4-methylcatechol and 2% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
I204V
-
synthesizes 13% 3-methylcatechol, 83% 4-methylcatechol and 5% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
A405G
-
synthesizes 17% 3-methylcatechol, 83% 4-methylcatechol from substrate 3-nitrotoluene
-
I204A
-
synthesizes 2% 3-methylcatechol, 97% 4-methylcatechol and 1% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
-
I204T
-
synthesizes 5% 3-methylcatechol, 93% 4-methylcatechol and 2% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
-
I204V
-
synthesizes 13% 3-methylcatechol, 83% 4-methylcatechol and 5% 3-nitrobenzyl alcohol from substrate 3-nitrotoluene
-
F293H
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene
F293I
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene
F293Q
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene. Mutant is 2.5 times faster than wild-type at oxidizing 2,6-dinitrotoluene while retaining a similar Km for the substrate
I350F
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene. Most mononitrotoluene oxidation products formed by the N258V mutant are nitrobenzyl alcohols rather than catechols
I350T
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene
N258V
mutation in alpha-subunit of oxygenase, residue is important for determining regiospecificity with nitroarene substrates and enantiospecificity with naphthalene. Up to 99% of the mononitrotoluene oxidation products formed by the N258V mutant are nitrobenzyl alcohols rather than catechols
F350T
-
contrary to wild-type, mutant produces 3-methyl-4-nitrocatechol from 2,6-dinitrotoluene and 3-amino-4-methyl-5-nitrocatechol and 2-amino-4,6-dinitrobenzyl alcohol from 2-amino-4,6-dinitrotoluene, and mutant releases nitrite from 2,3-dinitrotoluene sixfold faster than wild-type
F350T/G407S
-
double mutant increases the rate of oxidation of 2,3-dinitrotoluene, 2,6-dinitrotoluene , and 2-amino-4,6-dinitrotoluene threefold relative to variant F350T
G50S/L225R/A269T
-
mutant displays increased rate of 4-amino-2-nitrotoluene oxidation and additionally produces oxidation product 4-amino-2-nitrocresol (enhanced 11fold relative to wild-type) as well as 4-amino-2-nitrobenzyl alcohol
L225R
-
12fold faster generation of 4-amino-2-nitrocresol and production of 4-amino-2-nitrobenzyl alcohol from 4-amino-2-nitrotoluene as well as 24fold faster generation of nitrite and 15fold faster generation of 2,3-dinitrobenzyl alcohol from 2,3-dinitrotoluene
F350T
-
contrary to wild-type, mutant produces 3-methyl-4-nitrocatechol from 2,6-dinitrotoluene and 3-amino-4-methyl-5-nitrocatechol and 2-amino-4,6-dinitrobenzyl alcohol from 2-amino-4,6-dinitrotoluene, and mutant releases nitrite from 2,3-dinitrotoluene sixfold faster than wild-type
-
F350T/G407S
-
double mutant increases the rate of oxidation of 2,3-dinitrotoluene, 2,6-dinitrotoluene , and 2-amino-4,6-dinitrotoluene threefold relative to variant F350T
-
G50S/L225R/A269T
-
mutant displays increased rate of 4-amino-2-nitrotoluene oxidation and additionally produces oxidation product 4-amino-2-nitrocresol (enhanced 11fold relative to wild-type) as well as 4-amino-2-nitrobenzyl alcohol
-
L225R
-
12fold faster generation of 4-amino-2-nitrocresol and production of 4-amino-2-nitrobenzyl alcohol from 4-amino-2-nitrotoluene as well as 24fold faster generation of nitrite and 15fold faster generation of 2,3-dinitrobenzyl alcohol from 2,3-dinitrotoluene
-
additional information