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an aliphatic amide = a nitrile + H2O
an aliphatic amide = a nitrile + H2O
light
-
-
-
an aliphatic amide = a nitrile + H2O
the iron-type enzyme is photoreactive, it loses the catalytic activity through aerobic incubation in the dark and recovers it by light irradiation
-
an aliphatic amide = a nitrile + H2O
N-771 and N-774 strains can be inactivated in the dark and reactivated by light
-
an aliphatic amide = a nitrile + H2O
the activity of the enzyme in intact cells increases on light irradiation and gradually decreases in the dark. For purified enzyme no differences are detected when kept in dark or light-irradiated
-
an aliphatic amide = a nitrile + H2O
monitoring of binding of substrates and their analogues to the active pocket via the NO bands
-
an aliphatic amide = a nitrile + H2O
substrate binding occurs via breathing and flip-flop mechanisms
-
an aliphatic amide = a nitrile + H2O
possible role of water and active center residues in reaction mechanism is shown
-
an aliphatic amide = a nitrile + H2O
reaction mechanism, overview
-
an aliphatic amide = a nitrile + H2O
first- and second-shell reaction mechanism, a tyrosine residue acts as catalytic base, modelling, detailed overview
-
an aliphatic amide = a nitrile + H2O
modeling of the catalytic mechanism of nitrile hydratase by semi-empirical quantum mechanical calculation using the enzyme crystal structure, PDB code 1IRE, overview. Active site activation is the first step of NHase catalysis, in which the Co2+ coordinated to a water molecule forms a Co-OH complex mediated by the oxidized alpha-CEA113. Then the oxygen atom in the Co-OH attacks the C atom in the -CN triple bond of acrylonitrile, forming a precursor of acrylamide, proton rearrangement happens transforming the precursor into the final product of acrylamide, under the assistance of the hydrogen atom in the -OH group of alpha-Ser112
an aliphatic amide = a nitrile + H2O
reaction mechanism, first-shell mechanism of CoIII-NHase involving Tyr68 as catalytic base, deprotonated Tyr68 is proposed to abstract a proton from the nucleophilic water molecule, thus activating it for attack on the metal-bound substrate, modelling, detailed overview
-
an aliphatic amide = a nitrile + H2O
thermal-stable mechanism of thermophilic nitrile hydratases, molecular dynamic simulation, overview
-
an aliphatic amide = a nitrile + H2O
thermal-stable mechanism of thermophilic nitrile hydratases, molecular dynamic simulation, overview
an aliphatic amide = a nitrile + H2O
water dynamics and catalytic mechanism, a water molecule bound to the metal ion directly attacks the nitrile carbon, overview. Dynamics of the active site channel, NO diffusion paths, and water molecules positions are key components in the functioning of this important industrial enzyme
-
an aliphatic amide = a nitrile + H2O
role of residues in the active site and enzymatic reaction mechanism. Cys146 acts as the nucleophile, Glu42 as the general base, Lys113/Glu42 as the general acid, WatA as the hydrolytic water and Nf_Lys113 and N_Phe147 form the oxyanion hole, hydrogen bonding network in the active site of Nit structure, overview
-
an aliphatic amide = a nitrile + H2O
detailed reaction mechanism using large quantum-mechanical active site models, overview. The attack of Cys114-SO- on the coordinated nitrile forms a cyclic intermediate. Cys109-S-S-Cys114 disulfide formation promotes cleavage of the latter to give the amide. Active-site regeneration occurs through attack of water on the disulfide, putative cyclic intermediate structure, overview
-
an aliphatic amide = a nitrile + H2O
mechanism of action for the hydration of nitriles by NHase, overview. The cysteine-sulfenic acid ligand acts as the catalytic nucleophile. The first step in catalysis involves the direct ligation of the nitrile to the active site lowspin, trivalent metal ion. One proton transfer occurs between the alphaCys113-OH ligand and the nitrile N-atom, while the second transfer occurs between the water molecule that reforms alphaCys113-OH and the newly forming imidate N-atom
an aliphatic amide = a nitrile + H2O
first- and second-shell reaction mechanism, a tyrosine residue acts as catalytic base, modelling, detailed overview
-
-
an aliphatic amide = a nitrile + H2O
N-771 and N-774 strains can be inactivated in the dark and reactivated by light
-
-
an aliphatic amide = a nitrile + H2O
the activity of the enzyme in intact cells increases on light irradiation and gradually decreases in the dark. For purified enzyme no differences are detected when kept in dark or light-irradiated
-
-
an aliphatic amide = a nitrile + H2O
possible role of water and active center residues in reaction mechanism is shown
-
-
an aliphatic amide = a nitrile + H2O
reaction mechanism, overview
-
-
an aliphatic amide = a nitrile + H2O
reaction mechanism, first-shell mechanism of CoIII-NHase involving Tyr68 as catalytic base, deprotonated Tyr68 is proposed to abstract a proton from the nucleophilic water molecule, thus activating it for attack on the metal-bound substrate, modelling, detailed overview
-
-
an aliphatic amide = a nitrile + H2O
modeling of the catalytic mechanism of nitrile hydratase by semi-empirical quantum mechanical calculation using the enzyme crystal structure, PDB code 1IRE, overview. Active site activation is the first step of NHase catalysis, in which the Co2+ coordinated to a water molecule forms a Co-OH complex mediated by the oxidized alpha-CEA113. Then the oxygen atom in the Co-OH attacks the C atom in the -CN triple bond of acrylonitrile, forming a precursor of acrylamide, proton rearrangement happens transforming the precursor into the final product of acrylamide, under the assistance of the hydrogen atom in the -OH group of alpha-Ser112
-
-
an aliphatic amide = a nitrile + H2O
mechanism of action for the hydration of nitriles by NHase, overview. The cysteine-sulfenic acid ligand acts as the catalytic nucleophile. The first step in catalysis involves the direct ligation of the nitrile to the active site lowspin, trivalent metal ion. One proton transfer occurs between the alphaCys113-OH ligand and the nitrile N-atom, while the second transfer occurs between the water molecule that reforms alphaCys113-OH and the newly forming imidate N-atom
-
-
an aliphatic amide = a nitrile + H2O
thermal-stable mechanism of thermophilic nitrile hydratases, molecular dynamic simulation, overview
-
-
an aliphatic amide = a nitrile + H2O
thermal-stable mechanism of thermophilic nitrile hydratases, molecular dynamic simulation, overview
-
-
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(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbamide
(1R,3R)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-3-phenylcyclopropanecarbamide
(1R,3S)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3S)-3-phenylcyclopropanecarbamide
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbonitrile + H2O
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbamide
(25R)-3beta-hydroxycholest-5-en-27-oate
?
-
-
-
-
?
(2R)-2-hydroxy-3-methylbutanenitrile + H2O
(2R)-2-hydroxy-3-methylbutanamide
-
-
-
-
?
(2R)-2-hydroxybut-3-enenitrile + H2O
(2R)-2-hydroxybut-3-enamide
-
-
-
-
?
(2R)-2-hydroxybutanenitrile + H2O
(2R)-2-hydroxybutanamide
-
-
-
-
?
(2R)-2-hydroxyhexanenitrile + H2O
(2R)-2-hydroxyhexanamide
-
-
-
-
?
(2R)-2-hydroxypentanenitrile + H2O
(2R)-2-hydroxypentanamide
-
-
-
-
?
(R)-2-chloromandelonitrile + H2O
(R)-2-chloromandelamide
at 100% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
(R)-mandelonitrile + H2O
(R)-mandelamide
(R,S)-2-(4-nitrophenyl)-propionitrile + H2O
?
-
39% conversion
-
-
?
(R,S)-2-bromopropionitrile + H2O
?
-
47% conversion
-
-
?
(R,S)-2-chloropropionitrile + H2O
?
-
48% conversion
-
-
?
(R,S)-2-phenylbutyronitrile + H2O
?
-
51% conversion
-
-
?
(R,S)-2-phenylpropionitrile + H2O
?
-
43% conversion
-
-
?
(R,S)-3-oxo-2-phenylbutyronitrile + H2O
?
-
43% conversion
-
-
?
(S)-3-benzoyloxypentanedinitrile + H2O
3-amino-1-(2-amino-2-oxoethyl)-3-oxopropyl benzoate
-
substrate conversion: 38.5%, enantiomeric excess: 68.2
-
-
r
(S)-mandelonitrile + H2O
(S)-mandelamide
1,1,3,3,-tetramethylbutylisonitrile + H2O
1,1,3,3,-tetramethylisobutylamide
1-(4-bromo-phenyl)-aziridine-2-carbonitrile + H2O
1-(4-bromophenyl)aziridine-2-carboxamide
-
-
-
-
r
1-(4-methoxy-phenyl)-aziridine-2-carbonitrile + H2O
1-(4-methoxyphenyl)aziridine-2-carboxamide
-
-
-
-
r
1-cyanocyclohexaneacetonitrile + H2O
1-cyanocyclohexaneacetamide
1-naphthylnitrile + H2O
1-naphthylamide
17alpha-cyanomethyl-17beta-hydroxy-estra-4,9-dien-3-one + H2O
17alpha-acetamido-estra-1,3,5(10),9(11)-tetraene-3,17beta-diol
-
the steroidal group is metabolized very slowly
-
?
2(R)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(R)-(4-chloro-phenyl)-3-methyl-butyramide
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
2,2-dimethylcyclopropanecarbonitrile + H2O
?
2,3,4,5,6-pentafluorobenzonitrile + H2O
2,3,4,5,6-pentafluorobenzamide
-
-
-
-
?
2,3-dihydro-benzo(1,4)dioxine-2-carbonitrile + H2O
2,3-dihydro-1,4-benzodioxine-2-carboxamide
-
substrate conversion: 45.1%, enantiomeric excess: 0
-
-
r
2,6-dichlorobenzamide + H2O
2,6-dichlorobenzoic acid
2,6-difluorobenzonitrile + H2O
2,6-difluorobenzamide
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
2-aminopropionitrile + H2O
2-aminopropionic acid amide
-
90% of the activity with propionitrile
-
-
?
2-bromobenzonitrile + H2O
2-bromobenzamide
-
-
-
-
ir
2-chlorobenzaldehyde + HCN + H2O
(R)-2-chloromandelonitrile
-
-
90% conversion to alpha-hydroxy nitrile
-
?
2-chlorobenzonitrile + H2O
2-chlorobenzamide
-
-
-
-
ir
2-cyanobenzamide + H2O
benzene-1,2-dicarboxamide
2-cyanopyridine + H2O
pyridine-2-carbamide
2-fluorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
2-fluorobenzonitrile + H2O
2-fluorobenzamide
-
-
-
-
ir
2-furonitrile + H2O
2-furoamide
2-hydroxy-4-phenylbutanenitrile + H2O
?
-
-
-
?
2-hydroxy-4-phenylbutyronitrile + H2O
2-hydroxy-4-phenylbutyramide
-
-
-
?
2-hydroxymethyl-3-phenyl-propionitrile + H2O
2-benzyl-3-hydroxypropanamide
-
-
-
-
r
2-hydroxypropionitrile + H2O
2-hydroxypropionic acid amide
2-methoxybenzonitrile + H2O
2-methoxybenzamide
-
-
-
-
ir
2-methoxymethyl-3-phenyl-propionitrile + H2O
2-benzyl-3-methoxypropanamide
-
-
-
-
r
2-methyl-3-butenenitrile + H2O
?
2-methylbenzonitrile + H2O
2-methylbenzamide
-
-
-
-
ir
2-naphthylacetonitrile + H2O
2-naphthylacetamide
2-nitro-5-thiocyanato-benzoic acid + H2O
?
-
-
-
-
?
2-nitrobenzaldehyde + HCN + H2O
? + H2O
-
-
20% conversion to alpha-hydroxy nitrile
-
?
2-phenylacetonitrile + H2O
2-phenylpropionamide
-
-
-
-
?
2-phenylbutyronitrile + H2O
2-phenylbutyramide
-
used as well as phenylacetonitrile
-
-
?
2-phenylglycinonitrile + H2O
aminoacetamide
-
used as well as phenylacetonitrile
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
3,4,5-trimethoxybenzonitrile + H2O
3,4,5-trimethoxybenzamide
3,4-dimethoxybenzonitrile + H2O
3,4-dimethoxybenzaldehyde + NH3
3-(1-cyanoethyl)benzoic acid + H2O
?
3-(trifluoromethyl)benzonitrile + H2O
3-(trifluoromethyl)benzamide
3-(trifluoromethyl)pyridine-4-carbonitrile + H2O
3-(trifluoromethyl)pyridine-4-carboxamide
-
-
-
-
ir
3-allyloxy-4-phenyl-butyronitrile + H2O
4-phenyl-3-(prop-2-en-1-yloxy)butanamide
-
-
-
-
r
3-aminopropionitrile + H2O
3-aminopropionic acid amide
-
2.7% of the activity with propionitrile
-
-
?
3-benzoyloxyglutaronitrile + H2O
(S)-3-benzoyloxy-4-cyanobutyramide
3-benzyloxy-3-vinyl-propionitrile + H2O
3-(benzyloxy)pent-4-enamide
-
-
-
-
r
3-benzyloxy-pentanonitrile + H2O
3-(benzyloxy)pentanamide
-
-
-
-
r
3-benzyloxyglutaronitrile + H2O
3-benzyloxy-4-cyanobutyramide
3-bromobenzonitrile + H2O
3-bromobenzamide
-
5% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-chlorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
3-chlorobenzonitrile + H2O
3-chlorobenzamide
3-cyanopyridine + H2O
nicotinamide
3-cyanopyridine + H2O
pyridine-3-carbamide
3-cyanopyridine + H2O
pyridine-3-carboxamide
3-fluorobenzonitrile + H2O
3-fluorobenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-hydroxy-3-phenylpropionitrile + H2O
3-hydroxy-3-phenylpropionamide
3-hydroxybenzonitrile + H2O
3-hydroxybenzamide
3-hydroxybutryronitrile + H2O
3-hydroxybutyramide
3-hydroxypropionitrile + H2O
3-hydroxypropanamide
-
35% of the activity with propionitrile
-
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropionamide
3-hydroxyvaleronitrile + H2O
3-hydroxyvaleramide
3-methoxybenzonitrile + H2O
3-methoxybenzamide
-
3% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-methylbenzonitrile + H2O
3-methylbenzamide
3-phenoxymandelonitrile + H2O
3-phenoxymandelamine
at 10% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
3-phenylpropanenitrile + H2O
3-phenylpropanamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
3-phenylpropionitrile + H2O
3-phenylpropionamide
-
used as well as phenylacetonitrile
-
-
?
4-(trifluoromethyl)benzonitrile + H2O
4-(trifluoromethyl)benzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-acetylbenzonitrile + H2O
4-acetylbenzamide
-
above 99% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-aminobenzonitrile + H2O
4-aminobenzamide
4-bromobenzonitrile + H2O
4-bromobenzamide
4-chloro-3-hydroxybutanenitrile + H2O
?
-
-
-
?
4-chloro-3-hydroxybutyronitrile + H2O
4-chloro-3-hydroxybutyramide
-
the following reaction by an amidase leads to the correspondend carboxylic acid
-
-
?
4-chlorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
4-chlorobenzonitrile + H2O
4-chlorbenzamide
-
-
-
-
ir
4-chlorobenzonitrile + H2O
4-chlorobenzamide
4-chlorobutyronitrile + H2O
4-chlorobutyramide
-
-
-
?
4-cyanobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
4-cyanobenzamide + H2O
benzene-1,4-dicarboxamide
4-cyanobenzoic acid + H2O
4-(aminocarbonyl)benzoic acid
-
-
-
-
?
4-cyanopyridine + H2O
isonicotinamide
4-fluorobenzonitrile + H2O
4-fluorbenzamide
-
-
-
-
ir
4-fluorobenzonitrile + H2O
4-fluorobenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
4-hydroxybenzaldehyde + HCN + H2O
? + H2O
-
-
55% conversion to alpha-hydroxy nitrile
-
?
4-hydroxybenzonitrile + H2O
4-hydroxybenzamide
-
-
-
-
?
4-hydroxybenzonitrile + H2O
4-hydroxybenzoic acid amide
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetamide
4-methoxybenzonitrile + H2O
4-methoxybenzamide
-
above 99% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-methylbenzaldehyde + HCN + H2O
? + H2O
-
-
51% conversion to alpha-hydroxy nitrile
-
?
4-methylbenzonitrile + H2O
4-methylbenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-methylmandelonitrile + H2O
4-methylmandelamine
at 60% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
4-nitrobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
5-cyanovaleramide
adiponitrile + H2O
5-cyanovaleric acid + H2O
6-amino-6-oxohexanoic acid
-
NilFe and NilCo
-
-
r
5-hydroxymethyl-2-furonitrile + H2O
5-hydroxymethyl-2-furamide
acetamiprid + H2O
(1E)-N'-carbamoyl-N-[(6-chloropyridin-3-yl)methyl]-N-methylethanimidamide
hydration at 22.41% compared to the activity with thiacloprid
-
-
?
acetonitrile + H2O
acetamide
acrylamide + H2O
acrylonitrile
acrylonitrile + H2O
2-propenoic acid amide
acrylonitrile + H2O
acrylamide
4.2.1.84 nitrile hydratase
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