Information on EC 3.5.5.1 - nitrilase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
3.5.5.1
-
RECOMMENDED NAME
GeneOntology No.
nitrilase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a nitrile + 2 H2O = a carboxylate + NH3
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of amide bond
hydrolysis of C-N bond
nitrile hydrolysis
-
-
N-bond hydrolysis
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Aminobenzoate degradation
-
-
Cyanoamino acid metabolism
-
-
indole glucosinolate activation (herbivore attack)
-
-
indole-3-acetate biosynthesis II
-
-
indole-3-acetate biosynthesis V (bacteria and fungi)
-
-
Microbial metabolism in diverse environments
-
-
Nitrogen metabolism
-
-
Styrene degradation
-
-
Tryptophan metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
nitrile aminohydrolase
Acts on a wide range of aromatic nitriles including (indol-3-yl)acetonitrile, and also on some aliphatic nitriles, and on the corresponding acid amides. cf. EC 4.2.1.84 nitrile hydratase.
CAS REGISTRY NUMBER
COMMENTARY hide
157297-79-5
Arabidopsis thaliana columbiana and Lansberg gene NIT2
157575-01-4
Arabidopsis thaliana columbiana gene NIT3
157575-02-5
Arabidopsis thaliana columbiana gene NIT4
205331-43-7
Arabidopsis thaliana nit2 isoenzyme2
205394-78-1
Arabidopsis thaliana nit3 isoenzyme3
205394-80-5
Arabidopsis thaliana nit1 isoenzyme1
9024-90-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain AK226
-
-
Manually annotated by BRENDA team
strain AK226
-
-
Manually annotated by BRENDA team
DSM 6336
-
-
Manually annotated by BRENDA team
strain MTCC 126
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain J-1
-
-
Manually annotated by BRENDA team
strain OxB-1
-
-
Manually annotated by BRENDA team
UG-5B
-
-
Manually annotated by BRENDA team
strain E9
-
-
Manually annotated by BRENDA team
strain E9
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
chinese cabbage
-
-
Manually annotated by BRENDA team
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GenBank
Manually annotated by BRENDA team
no activity in Allium cepa
-
-
-
Manually annotated by BRENDA team
no activity in Citrus limonium
-
-
-
Manually annotated by BRENDA team
no activity in Croton sp.
-
-
-
Manually annotated by BRENDA team
no activity in Cucumis sativus
-
-
-
Manually annotated by BRENDA team
no activity in Ginkgo biloba
-
-
-
Manually annotated by BRENDA team
no activity in Helianthus annuus
-
-
-
Manually annotated by BRENDA team
no activity in Heliconia sp.
-
-
-
Manually annotated by BRENDA team
no activity in Impatiens balsamina
-
-
-
Manually annotated by BRENDA team
no activity in Iris sp.
-
-
-
Manually annotated by BRENDA team
no activity in Kalanchoe blossfeldiana
-
-
-
Manually annotated by BRENDA team
no activity in Lilium sp.
-
-
-
Manually annotated by BRENDA team
no activity in Monstera deliciosa
-
-
-
Manually annotated by BRENDA team
no activity in Nerium oleander
-
-
-
Manually annotated by BRENDA team
no activity in Onoclea sensibilis
-
-
-
Manually annotated by BRENDA team
no activity in Pelargonium zonale
-
-
-
Manually annotated by BRENDA team
no activity in Pteridium aquilinum
-
-
-
Manually annotated by BRENDA team
no activity in Rosa sp.
-
-
-
Manually annotated by BRENDA team
no activity in Solanum lycopersicum
-
-
-
Manually annotated by BRENDA team
no activity in Tradescantia virginiana
-
-
-
Manually annotated by BRENDA team
no activity in Xanthium pennsylvanicum
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain 11387
-
-
Manually annotated by BRENDA team
strain EBC 191
-
-
Manually annotated by BRENDA team
strain 11388
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
strain 11401, re-classified from Agrobacterium to Rhizobium
-
-
Manually annotated by BRENDA team
strain 11401, re-classified from Agrobacterium to Rhizobium
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-
Manually annotated by BRENDA team
strain CCTCC.M.205114
-
-
Manually annotated by BRENDA team
strain CCTCC.M.205114
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-
Manually annotated by BRENDA team
strain J1
-
-
Manually annotated by BRENDA team
Rhodococcus sp. ATCC39484
strain ATCC39484
-
-
Manually annotated by BRENDA team
Rhodococcus sp. NCIMB 11215
-
-
-
Manually annotated by BRENDA team
Rhodococcus sp. NCIMB 11216
-
-
-
Manually annotated by BRENDA team
Rhodococcus sp. NDB 1165
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene nit1
UniProt
Manually annotated by BRENDA team
line B73
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2-chlorophenyl)(hydroxy)acetonitrile + H2O
2-(2-chlorophenyl)-2-hydroxyacetamide
show the reaction diagram
(2-ethylphenyl)(hydroxy)acetonitrile + H2O
2-(2-ethylphenyl)-2-hydroxyacetamide
show the reaction diagram
(2S)-1-[(4-methylphenyl)sulfonyl]piperidine-2-carbonitrile + H2O
?
show the reaction diagram
(3E)-2-hydroxypent-3-enenitrile + H2O
(3E)-2-hydroxypent-3-enamide
show the reaction diagram
(3R)-1-[(4-methylphenyl)sulfonyl]piperidine-3-carbonitrile + H2O
?
show the reaction diagram
(3R)-3-methyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine + H2O
?
show the reaction diagram
(3S)-3-(2,4-difluorophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(2,4-difluorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
(3S)-3-(3-methoxyphenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(3-methoxyphenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
(3S)-3-(3-nitrophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(3-nitrophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
(3S)-3-(4-bromophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-bromophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
(3S)-3-(4-chlorophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-chlorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
(3S)-3-(4-cyanophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-cyanophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
-
92% yield, 95% enantiomeric excess
-
-
?
(3S)-3-(4-fluorophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-fluorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
-
93% yield, 99% enantiomeric excess
-
-
?
(3S)-3-(4-methoxyphenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-methoxyphenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
-
91% yield, 99% enantiomeric excess
-
-
?
(3S)-3-(4-methylphenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-methylphenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
-
91% yield, 99% enantiomeric excess
-
-
?
(3S)-3-(4-nitrophenyl)-3-hydroxypropanenitrile + H2O
(3S)-3-(4-nitrophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
-
87% yield, 97% enantiomeric excess
-
-
?
(3S)-3-hydroxy-3-phenylpropanenitrile + H2O
(3S)-3-hydroxy-3-phenylpropanoic acid + NH3
show the reaction diagram
-
90% yield, 99% enantiomeric excess
-
-
?
(3S)-isobutylsuccinonitrile + H2O
(3S)-3-cyano-5-methyl hexanoic acid
show the reaction diagram
-
specific for the (3S)-isomer
-
-
?
(E/Z)-2-methylbut-2-enenitrile + H2O
(E)-2-methylbut-2-enoic acid + NH3
show the reaction diagram
(methylthio)acetonitrile + H2O
(methylthio)acetic acid + NH3
show the reaction diagram
(methylthio)acetonitrile + H2O
(methylthio)indole-3-acetic acid + NH3
show the reaction diagram
-
-
-
?
(phenylthio)acetonitrile + H2O
(phenylthio)indole-3-acetic acid + NH3
show the reaction diagram
-
-
-
?
(R)-2-chloromandelonitrile + H2O
(R)-2-chloromandelic acid + (S)-2-chloromandelic acid + NH3
show the reaction diagram
(R,S)-2-hydroxy-2-phenylacetonitrile + 2 H2O
(R)-2-hydroxy-2-phenylacetic acid + NH3
show the reaction diagram
(R,S)-2-phenylpropionitrile + H2O
?
show the reaction diagram
(R,S)-mandelonitrile + H2O
(R)-(-)-mandelic acid + (S)-mandelonitrile
show the reaction diagram
(S)-2-acetoxy-2-phenylacetonitrile + H2O
(S)-2-acetoxy-2-phenylacetic acid + (S)-2-acetoxy-2-phenylacetamide
show the reaction diagram
1,2-phenylenediacetonitrile + H2O
? + NH3
show the reaction diagram
0.063% activity compared to iminodiacetonitrile
-
-
?
1,3-benzodinitrile + H2O
benzoic acid + NH3
show the reaction diagram
-
-
-
?
1,3-dicyanobenzene + H2O
?
show the reaction diagram
-
8.4% activity compared to benzonitrile
-
-
?
1,4-benzodinitrile + H2O
?
show the reaction diagram
-
-
-
-
?
1,4-benzodinitrile + H2O
benzoic acid + NH3
show the reaction diagram
-
best substrate
-
?
1,4-dicyanobenzene + H2O
?
show the reaction diagram
-
79.5% activity compared to benzonitrile
-
-
?
1,4-dicyanobutane + H2O
? + NH3
show the reaction diagram
27.1% activity compared to iminodiacetonitrile
-
-
?
1,4-dicyanobutane + H2O
hexanedioic acid + NH3
show the reaction diagram
1,5-dicyanopentane + H2O
heptanedioic acid + NH3
show the reaction diagram
-
90% yield
-
-
?
1,6-dicyanohexane + H2O
octanedioic acid + NH3
show the reaction diagram
-
88% yield
-
-
?
1-(cyanoacetyl)pyrrolidine + H2O
? + NH3
show the reaction diagram
low activity
-
-
?
1-[(4-methylphenyl)sulfonyl]piperidine-4-carbonitrile + H2O
?
show the reaction diagram
2 (R,S)-mandelonitrile + 4 H2O
(R)-mandelic acid + NH3 + (S)-mandelonitrile
show the reaction diagram
2 phenylacetonitrile + H2O
2-phenylacetate + NH3
show the reaction diagram
-
-
-
-
?
2,2-dimethylcyclopropyl cyanide + 2 H2O
2,2-dimethylcyclopropyl carboxylate + NH3
show the reaction diagram
-
-
-
?
2,4-dichlorophenyl acetonitrile + 2 H2O
2,4-dichlorophenyl acetic acid + NH3
show the reaction diagram
2,4-pyridinedicarbonitrile + H2O
2-cyanopyridine-4-carboxylic acid + NH3
show the reaction diagram
-
7% activity compared to benzonitrile
-
-
?
2,6-pyridinedicarbonitrile + H2O
6-cyanopyridine-2-carboxylic acid + NH3
show the reaction diagram
-
5% activity compared to benzonitrile
-
-
?
2-amino-2,3-dimethylbutanenitrile + 2 H2O
? + NH3
show the reaction diagram
-
-
-
?
2-amino-4-methylbenzonitrile + 2 H2O
2-amino-4-methylbenzoic acid + NH3
show the reaction diagram
2-amino-5-chloro-benzonitrile + 2 H2O
2-amino-5-chloro-benzoic acid + NH3
show the reaction diagram
2-amino-6-chloro-benzonitrile + 2 H2O
2-amino-6-chloro-benzoic acid + NH3
show the reaction diagram
-
good substrate, when the cells are induced by benzonitrile
-
-
?
2-aminobenzonitrile + 2 H2O
2-aminobenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
2-aminobutyronitrile + 2 H2O
2-aminobutyric acid + NH3
show the reaction diagram
high activity
-
-
?
2-aminobutyronitrile + H2O
2-aminobutyric acid + NH3
show the reaction diagram
-
-
-
?
2-aminopropionitrile + H2O
2-aminopropionic acid + NH3
show the reaction diagram
-
low activity
-
?
2-bromobenzonitrile + H2O
2-bromobenzoic acid + NH3
show the reaction diagram
-
best substrate of strain NCIB11216 and strain NCIB11215
-
-
?
2-chloro-2-phenylacetonitrile + H2O
2-chloro-2-phenylacetic acid + 2-chloro-2-phenylacetamide
show the reaction diagram
2-chloro-3-cyanopyridine + H2O
?
show the reaction diagram
-
0.21% activity compared to 3-cyanopyridine
-
-
?
2-chloro-4-cyanopyridine + H2O
?
show the reaction diagram
2-chloromandelonitrile + 2 H2O
2-chloromandelic acid + NH3
show the reaction diagram
2-cyanopyrazine + H2O
pyrazine-2-carboxylic acid + NH3
show the reaction diagram
-
-
-
-
-
2-cyanopyridine
picolinic acid
show the reaction diagram
-
-
-
-
-
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid
show the reaction diagram
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
show the reaction diagram
2-cyanopyridine + H2O
2-pyridine carboxylic acid + NH3
show the reaction diagram
2-cyanopyridine + H2O
2-pyridinecarboxylic acid + NH3
show the reaction diagram
-
7% activity compared to benzonitrile
-
-
?
2-cyanopyridine + H2O
?
show the reaction diagram
-
1.5% activity compared to 3-cyanopyridine
-
-
?
2-cyanopyridine + H2O
? + NH3
show the reaction diagram
2-cyanopyridine + H2O
pyridine-2-carboxylic acid + NH3
show the reaction diagram
-
14.2% activity compared to benzonitrile
-
-
?
2-fluorobenzonitrile + H2O
2-fluorobenzoic acid + NH3
show the reaction diagram
2-furanocarbonitrile + H2O
2-furanocarboxylic acid + NH3
show the reaction diagram
2-furanocarbonitrile + H2O
furan-2-carboxylic acid + NH3
show the reaction diagram
-
best substrate
-
?
2-furanocarbonnitrile + H2O
2-furanocarboxylic acid + NH3
show the reaction diagram
2-hydroxy-2-phenylpropionitrile + 2 H2O
2-hydroxy-2-phenylpropionic acid + NH3
show the reaction diagram
2-methyl-2-phenylpropionitrile + 2 H2O
2-methyl-2-phenylpropionic acid + NH3
show the reaction diagram
2-methylbutyronitrile + H2O
2-methylbutyric acid + NH3
show the reaction diagram
-
-
-
?
2-methylglutaronitrile + H2O
4-cyanopentanoic acid + NH3
show the reaction diagram
2-nitrobenzonitrile + H2O
2-nitrobenzoic acid + NH3
show the reaction diagram
-
strain NCIB11215
-
-
?
2-phenylacetonitrile + H2O
2-phenylacetic acid + NH3
show the reaction diagram
-
10.8% activity compared to benzonitrile
-
-
?
2-phenylacetonitrile + H2O
phenylacetate + NH3
show the reaction diagram
-
substrate for isozyme complex NIT4A/B2
-
-
?
2-phenylacetonitrile + H2O
phenylacetic acid + 2-phenylacetamide
show the reaction diagram
2-phenylglycinonitrile + 2 H2O
amino(phenyl)acetic acid + NH3
show the reaction diagram
2-phenylpropionitrile + H2O
2-phenylpropanoic acid + 2-phenylpropanamide
show the reaction diagram
2-phenylpropionitrile + H2O
2-phenylpropionic acid + NH3
show the reaction diagram
2-thiophenacetonitrile + H2O
2-thiophenacetic acid + NH3
show the reaction diagram
2-toluonitrile + H2O
NH3 + 2-methylbenzoate
show the reaction diagram
3,4,5-trimethoxybenzonitrile + 2 H2O
3,4,5-trimethoxybenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
3,5-dibromo-4-hydroxybenzonitrile + H2O
3,5-dibromo-4-hydroxybenzoic acid + NH3
show the reaction diagram
3,5-dichloro-4-hydroxybenzonitrile + H2O
3,5-dichloro-4-hydroxybenzoic acid + NH3
show the reaction diagram
3,5-diiodo-4-hydroxybenzonitrile + H2O
3,5-diiodo-4-hydroxybenzoic acid + NH3
show the reaction diagram
3-(2,4-dichlorophenyl)-3-hydroxypropanenitrile + H2O
(S)-3-(2,4-dichlorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(2-chlorophenyl)-3-hydroxypropanenitrile + H2O
3-(2-chlorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(4-chlorophenyl)-3-hydroxypropanenitrile + H2O
(S)-3-(4-chlorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(4-fluorophenyl)-3-hydroxypropanenitrile + H2O
(S)-3-(4-fluorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(4-hydroxyphenyl)propanenitrile + H2O
3-(4-hydroxyphenyl)propanoic acid + NH3
show the reaction diagram
-
-
-
-
?
3-aminobenzonitrile + H2O
3-aminobenzoic acid + NH3
show the reaction diagram
3-anilinoproprionitrile + 2 H2O
3-anilinopropionate + NH3
show the reaction diagram
-
-
-
?
3-bromo-4-hydroxybenzonitrile + H2O
3-bromo-4-hydroxybenzoate + NH3
show the reaction diagram
-
low activity
-
?
3-bromobenzonitrile + H2O
3-bromobenzoic acid + NH3
show the reaction diagram
3-chloro-4-fluorobenzonitrile + H2O
3-chloro-4-fluorobenzoic acid + NH3
show the reaction diagram
-
-
-
?
3-chlorobenzonitrile + 2 H2O
3-chlorobenzoate + NH3
show the reaction diagram
3-chlorobenzonitrile + 2 H2O
3-chlorobenzoic acid + NH3
show the reaction diagram
3-chlorobenzonitrile + H2O
3-chlorobenzoic acid + NH3
show the reaction diagram
3-cyanopyridine + 2 H2O
? + NH3
show the reaction diagram
50% of the activity with acrylonitrile
-
-
?
3-cyanopyridine + 2 H2O
nicotinic acid + NH3
show the reaction diagram
3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
show the reaction diagram
3-cyanopyridine + H2O
3-pyridinecarboxylic acid + NH3
show the reaction diagram
3-cyanopyridine + H2O
?
show the reaction diagram
-
-
-
?
3-cyanopyridine + H2O
? + NH3
show the reaction diagram
low activity
-
-
?
3-cyanopyridine + H2O
nicotinic acid + NH3
show the reaction diagram
3-cyanopyridine + H2O
pyridine-3-carboxylic acid + NH3
show the reaction diagram
-
32.4% activity compared to benzonitrile
-
-
?
3-fluorobenzonitrile + H2O
3-fluorobenzoic acid + NH3
show the reaction diagram
3-furonitrile + 2 H2O
furan 3-carboxylic acid + NH3
show the reaction diagram
-
-
-
-
?
3-hydroxy-3-(2-methoxyphenyl)propanenitrile + H2O
(S)-3-hydroxy-3-(2-methoxyphenyl)propanoic acid + NH3
show the reaction diagram
3-hydroxy-3-(3-methoxyphenyl)propanenitrile + H2O
(S)-3-hydroxy-3-(3-methoxyphenyl)propanoic acid + NH3
show the reaction diagram
-
nitrilase bll6402 catalyzes the enantioselective hydrolysis of aromatic beta-hydroxy nitriles to give (S)-enriched beta-hydroxy carboxylic acids with recovery of (R)-enriched beta-hydroxy nitriles
-
-
?
3-hydroxy-3-(4-methoxyphenyl)propanenitrile + H2O
(S)-3-hydroxy-3-(4-methoxyphenyl)propanoic acid + NH3
show the reaction diagram
-
nitrilase bll6402 catalyzes the enantioselective hydrolysis of aromatic beta-hydroxy nitriles to give (S)-enriched beta-hydroxy carboxylic acids with recovery of (R)-enriched beta-hydroxy nitriles
-
-
?
3-hydroxy-3-(4-methylphenyl)propanenitrile + H2O
(S)-3-hydroxy-3-(4-methylphenyl)propanoic acid + NH3
show the reaction diagram
-
nitrilase bll6402 catalyzes the enantioselective hydrolysis of aromatic beta-hydroxy nitriles to give (S)-enriched beta-hydroxy carboxylic acids with recovery of (R)-enriched beta-hydroxy nitriles
-
-
?
3-hydroxy-3-phenylpropanenitrile + H2O
(S)-3-hydroxy-3-phenylpropanoic acid + NH3
show the reaction diagram
-
nitrilase bll6402 catalyzes the enantioselective hydrolysis of aromatic beta-hydroxy nitriles to give (S)-enriched beta-hydroxy carboxylic acids with recovery of (R)-enriched beta-hydroxy nitriles
-
-
?
3-hydroxy-3-phenylpropionitrile + H2O
3-hydroxy-3-phenylpropionic acid + NH3
show the reaction diagram
3-hydroxy-glutaronitrile + 2 H2O
3-hydroxy-glutaric acid + NH3
show the reaction diagram
-
-
-
?
3-hydroxybenzonitrile + H2O
3-hydroxybenzoate + NH3
show the reaction diagram
-
8.4% activity compared to benzonitrile
-
-
?
3-hydroxybenzonitrile + H2O
3-hydroxybenzoic acid + NH3
show the reaction diagram
3-hydroxyglutaronitrile + H2O
(R)-3-hydroxy-4-cyanobutanoic acid + NH3
show the reaction diagram
-
-
-
-
?
3-hydroxyglutaronitrile + H2O
? + NH3
show the reaction diagram
1.15% activity compared to iminodiacetonitrile
-
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropanoate + NH3
show the reaction diagram
3-hydroxypropionitrile + H2O
3-hydroxypropionic acid + NH3
show the reaction diagram
2.57% activity compared to iminodiacetonitrile
-
-
?
3-hydroxyvaleronitrile + H2O
3-hydroxyvaleric acid + NH3
show the reaction diagram
3-methoxybenzonitrile + H2O
3-methoxybenzoic acid + NH3
show the reaction diagram
-
-
-
?
3-methylbenzonitrile + H2O
3-methylbenzoic acid + NH3
show the reaction diagram
3-nitrobenzonitrile + H2O
3-nitrobenzoic acid + NH3
show the reaction diagram
3-phenylpropanenitrile + H2O
phenylacetic acid + NH3
show the reaction diagram
3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
show the reaction diagram
3-phenylproprionitrile + H2O
3-phenylpropionic acid + NH3
show the reaction diagram
3-tolunitrile + H2O
3-methylbenzoate + NH3
show the reaction diagram
3-tolunitrile + H2O
3-methylbenzoic acid + NH3
show the reaction diagram
-
5.5% activity compared to benzonitrile
-
-
?
3-toluonitrile + H2O
NH3 + 3-methylbenzoate
show the reaction diagram
3-trans-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]prop-2-enenitrile + H2O
(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid + NH3
show the reaction diagram
4,5-dimethoxybenzonitrile + 2 H2O
4,5-dimethoxybenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-aminobenzonitrile + 2 H2O
4-aminobenzoic acid + NH3
show the reaction diagram
-
-
-
?
4-aminobenzonitrile + H2O
4-aminobenzoic acid + NH3
show the reaction diagram
4-bromobenzonitrile + 2 H2O
4-bromobenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-bromobenzonitrile + H2O
4-bromobenzoic acid + NH3
show the reaction diagram
4-chlorobenzonitrile + 2 H2O
4-chlorobenzoate + NH3
show the reaction diagram
4-chlorobenzonitrile + 2 H2O
4-chlorobenzoic acid + NH3
show the reaction diagram
4-chlorobenzonitrile + H2O
4-chlorobenzoate + NH3
show the reaction diagram
-
29.8% activity compared to benzonitrile
-
-
?
4-chlorobenzonitrile + H2O
4-chlorobenzoic acid + NH3
show the reaction diagram
4-chlorobenzonitrile + H2O
?
show the reaction diagram
4-chlorobutyronitrile + H2O
4-chlorobutyric acid + NH3
show the reaction diagram
4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid
show the reaction diagram
-
-
-
-
?
4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
show the reaction diagram
4-cyanopyridine + H2O
4-pyridinecarboxylic acid + NH3
show the reaction diagram
4-cyanopyridine + H2O
?
show the reaction diagram
4-cyanopyridine + H2O
? + NH3
show the reaction diagram
2.48% activity compared to iminodiacetonitrile
-
-
?
4-cyanopyridine + H2O
acrylic acid + NH3
show the reaction diagram
4-cyanopyridine + H2O
pyridine-4-carboxylic acid + NH3
show the reaction diagram
-
410.7% activity compared to benzonitrile
-
-
?
4-fluorobenzonitrile + 2 H2O
4-fluorobenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-fluorobenzonitrile + H2O
4-fluorobenzoic acid + NH3
show the reaction diagram
4-hydroxybenzonitrile + H2O
4-hydroxybenzoic acid + NH3
show the reaction diagram
4-hydroxybenzylcyanide + H2O
4-hydroxybenzoic acid + NH3
show the reaction diagram
low activity
-
-
?
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetic acid + NH3
show the reaction diagram
4-methoxy-2-nitrobenzonitrile + 2 H2O
4-methoxy-2-nitrobenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-methoxybenzonitrile + 2 H2O
4-methoxybenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-methoxybenzyl cyanide + 2 H2O
4-methoxyphenylacetic acid + NH3
show the reaction diagram
very low activity
-
-
?
4-methoxyphenylacetonitrile + H2O
4-methoxyphenylacetic acid + NH3
show the reaction diagram
-
0.6% activity compared to 3-cyanopyridine
-
-
?
4-methylbenzonitrile + H2O
4-methylbenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-nitrobenzonitrile + H2O
4-nitrobenzoic acid + NH3
show the reaction diagram
4-phenylbutyronitrile + H2O
4-phenylbutyric acid + NH3
show the reaction diagram
4-tolunitrile + H2O
4-methylbenzoate + NH3
show the reaction diagram
4-tolunitrile + H2O
4-methylbenzoic acid + NH3
show the reaction diagram
4-toluonitrile + H2O
NH3 + 4-methylbenzoate
show the reaction diagram
6-heptenenitrile + H2O
6-heptenoic acid + NH3
show the reaction diagram
-
substrate for isozyme NIT4A/B2
-
-
?
acetonitrile + 2 H2O
acetic acid + NH3
show the reaction diagram
acetonitrile + H2O
acetate + NH3
show the reaction diagram
acetonitrile + H2O
acetic acid + NH3
show the reaction diagram
acrylonitrile + 2 H2O
acrylic acid + NH3
show the reaction diagram
acrylonitrile + H2O
acrylic acid + NH3
show the reaction diagram
adiponitrile + 2 H2O
adipic acid + NH3
show the reaction diagram
adiponitrile + H2O
adipic acid + NH3
show the reaction diagram
allyl cyanide + H2O
prop-2-enoic acid + NH3
show the reaction diagram
allylcyanide + H2O
NH3 + but-3-enoic acid
show the reaction diagram
-
-
-
?
alpha,alpha-dimethylmalononitrile + H2O
alpha,alpha-dimethylmalonic acid + NH3
show the reaction diagram
-
93% yield
-
-
?
aminoacetonitrile + 2 H2O
aminoacetic acid + NH3
show the reaction diagram
25% of the activity with acrylonitrile
-
-
?
aminoacetonitrile + H2O
?
show the reaction diagram
aminoacetonitrile + H2O
aminoacetic acid + NH3
show the reaction diagram
-
9.0% activity compared to 3-cyanopyridine
-
-
?
benzamide + H2O
benzoate + NH3
show the reaction diagram
benzamide + H2O
benzoic acid + NH3
show the reaction diagram
-
catalysed by a highly purified nitrilase, but very low activity
-
?
benzonitrile + 2 H2O
benzoate + NH3
show the reaction diagram
benzonitrile + 2 H2O
benzoic acid + NH3
show the reaction diagram
benzonitrile + H2O
benzoic acid + benzamide
show the reaction diagram
-
100% activity
-
-
?
benzonitrile + H2O
benzoic acid + NH3
show the reaction diagram
benzyl (2S)-2-cyanopiperidine-1-carboxylate + H2O
?
show the reaction diagram
benzyl (3R)-3-methylpyrrolidine-1-carboxylate + H2O
?
show the reaction diagram
benzyl 4-cyanopiperidine-1-carboxylate + H2O
?
show the reaction diagram
benzyl cyanide + 2 H2O
phenylacetic acid + NH3
show the reaction diagram
-
-
-
-
?
benzyl [(1R,3R)-3-cyanocyclohexyl]carbamate + H2O
?
show the reaction diagram
benzyl [(1S,3R)-3-cyanocyclohexyl]carbamate + H2O
?
show the reaction diagram
beta-aminopropionitrile + H2O
beta-aminopropionic acid + NH3
show the reaction diagram
-
8.6% activity compared to 3-cyanopyridine
-
-
?
bromoxynil + H2O
3,5-dibromo-4-hydroxybenzoic acid + NH3
show the reaction diagram
bromoxynil + H2O
?
show the reaction diagram
butanedinitrile + H2O
? + NH3
show the reaction diagram
104.8% activity compared to iminodiacetonitrile
-
-
?
butyronitrile + H2O
butyric acid + NH3
show the reaction diagram
chloroacetonitrile + H2O
chloroacetic acid + NH3
show the reaction diagram
low activity
-
-
?
chloroxynil + H2O
?
show the reaction diagram
-
3',5-dihalogenated 4-hydroxybenzonitrile compound
-
-
?
cinnamonitrile + 2 H2O
cinnamic acid + NH3
show the reaction diagram
cinnamonitrile is a substrate for mutant enzyme K96R, no activity with wild-type enzyme
-
-
?
cinnamonitrile + H2O
?
show the reaction diagram
-
-
-
?
cinnamonitrile + H2O
cinnamic acid + NH3
show the reaction diagram
7.87% activity compared to iminodiacetonitrile
-
-
?
cis-1,2-dihydroxy-3-cyanocyclohexa-3,5-diene + H2O
5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid + NH3
show the reaction diagram
-
-
-
-
?
cis-5,6-dihydroxy-cyclohexa-1,3-diene-1-carbonitrile + H2O
(5R,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid + NH3
show the reaction diagram
crotonitrile + H2O
crotonic acid + NH3
show the reaction diagram
crotononitrile + H2O
?
show the reaction diagram
crotononitrile + H2O
crotonic acid + NH3
show the reaction diagram
crotononitrile + H2O
NH3 + (z)-but-2-en-1-ol
show the reaction diagram
cyano-5-valeramide + H2O
valeramide + NH3
show the reaction diagram
-
-
?
cyano-5-valeric acid + H2O
valeric acid + NH3
show the reaction diagram
-
-
?
cyclopropanecarbonitrile + H2O
cyclopropanecarboxylic acid + NH3
show the reaction diagram
-
-
-
?
decanedinitrile + H2O
9-cyanononanoic acid + NH3
show the reaction diagram
-
88% yield
-
-
?
DL-alpha-amino-4-methylthio butyronitrile + H2O
L-methionine + NH3
show the reaction diagram
-
-
-
?
DL-alpha-amino-n-capronitrile + H2O
L-norleucine + NH3
show the reaction diagram
-
-
-
?
DL-alpha-amino-n-valeronitrile + H2O
L-norvaline + NH3
show the reaction diagram
-
-
-
?
DL-alpha-aminoisocapronitrile + H2O
L-leucine + NH3
show the reaction diagram
-
-
-
?
DL-alpha-aminoisovaleronitrile + H2O
L-valine + NH3
show the reaction diagram
-
-
-
?
DL-alpha-aminopropionitrile + H2O
D-alanine + NH3
show the reaction diagram
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
show the reaction diagram
glutaronitrile + H2O
glutaric acid + NH3
show the reaction diagram
glycinonitrile + H2O
?
show the reaction diagram
-
23.27% activity compared to 3-cyanopyridine
-
-
?
glycolonitrile + 2 H2O
glycolic acid + NH3
show the reaction diagram
glycolonitrile + H2O
?
show the reaction diagram
glycolonitrile + H2O
ammonium glycolate + ?
show the reaction diagram
heptanenitrile + H2O
heptanoic acid + NH3
show the reaction diagram
-
-
-
?
hydrocinnamonitrile + H2O
hydrocinnamic acid + NH3
show the reaction diagram
-
-
-
-
?
hydrocinnamonitrile + H2O
hydrocinnamic acid acid + NH3
show the reaction diagram
hydroxy(3-phenoxyphenyl)acetonitrile + H2O
2-hydroxy-2-(3-phenoxyphenyl)acetamide
show the reaction diagram
hydroxy(4-methylphenyl)acetonitrile + H2O
2-hydroxy-2-(4-methylphenyl)acetamide
show the reaction diagram
-
-
-
?
hydroxy(phenyl)acetonitrile + H2O
?
show the reaction diagram
-
hydrolysis of alpha-hydroxynitriles is not enantioselective
-
-
?
hydroxy(phenyl)acetonitrile + H2O
hydroxy(phenyl)acetic acid + 2-hydroxy-2-phenylacetamide
show the reaction diagram
iminodiacetonitrile + 2 H2O
iminodiacetic acid + NH3
show the reaction diagram
iminodiacetonitrile + H2O
?
show the reaction diagram
iminodiacetonitrile + H2O
iminodiacetic acid + NH3
show the reaction diagram
iminodiacetonitrile + H2O
iminodiacidic acid + NH3
show the reaction diagram
-
58.07% activity compared to 3-cyanopyridine
-
-
?
indol-3-acetonitrile + H2O
indol-3-acetic acid + NH3
show the reaction diagram
indole acetonitrile + 2 H2O
indole acetic acid + NH3
show the reaction diagram
-
-
-
-
?
indole-3-acetonitrile + H2O
indol-3-acetic acid + NH3
show the reaction diagram
-
substrate for isozyme complex NIT4A/B2
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
show the reaction diagram
ioxynil + H2O
?
show the reaction diagram
isobutyronitrile + H2O
isobutyric acid + NH3
show the reaction diagram
-
4% activity compared to benzonitrile
-
-
?
isonicotinonitrile + H2O
isonicotinic acid + NH3
show the reaction diagram
isovaleronitrile + H2O
isovaleric acid + NH3
show the reaction diagram
-
47.17% activity compared to 3-cyanopyridine
-
-
?
lactonitrile + H2O
lactate + NH3
show the reaction diagram
-
-
-
?
lactonitrile + H2O
lactic acid + NH3
show the reaction diagram
-
4% activity compared to benzonitrile
-
-
?
m-tolunitrile + H2O
m-methylbenzoate + NH3
show the reaction diagram
-
-
-
-
?
malononitrile + 2 H2O
malonate + NH3
show the reaction diagram
-
-
-
?
malononitrile + H2O
malonic acid + NH3
show the reaction diagram
mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
show the reaction diagram
mandelonitrile + 2 H2O
mandelic acid + NH3
show the reaction diagram
mandelonitrile + H2O
mandelic acid + NH3
show the reaction diagram
2.38% activity compared to iminodiacetonitrile
-
-
?
methacrylonitrile + H2O
methylacrylic acid + NH3
show the reaction diagram
n-butyronitrile + H2O
n-butyric acid + NH3
show the reaction diagram
N-methyl-3-cyano-4-methoxy-2-pyridone + H2O
?
show the reaction diagram
-
-
-
-
?
n-valeronitrile + H2O
n-valeric acid + NH3
show the reaction diagram
-
-
-
?
N-[(1R,3R)-3-cyanocyclopentyl]-4-methylbenzenesulfonamide + H2O
?
show the reaction diagram
N-[(1S,3R)-3-cyanocyclohexyl]-4-methylbenzenesulfonamide + H2O
?
show the reaction diagram
N-[(1S,3R)-3-cyanocyclohexyl]benzamide + H2O
?
show the reaction diagram
N-[(1S,3R)-3-cyanocyclopentyl]-4-methylbenzenesulfonamide + H2O
?
show the reaction diagram
o-hydroxy-benzonitrile + H2O
o-hydroxy-benzoic acid + NH3
show the reaction diagram
p-aminobenzyl cyanide + H2O
?
show the reaction diagram
pentanenitrile + H2O
?
show the reaction diagram
-
1.6% activity compared to 3-cyanopyridine
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
show the reaction diagram
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
show the reaction diagram
phenylacetonitrile + H2O
phenylacetamide + phenylacetate + NH3
show the reaction diagram
phenylacetonitrile + H2O
phenylacetate + NH3
show the reaction diagram
phenylacetonitrile + H2O
phenylacetic acid + NH3
show the reaction diagram
low activity
-
-
?
phenylbutyronitrile + H2O
phenylbutyric acid + NH3
show the reaction diagram
phenylglycinenitrile + 2 H2O
phenylglycine + NH3
show the reaction diagram
-
-
-
?
phenylglycinonitrile + H2O
phenylglycine + NH3
show the reaction diagram
phenylpropionitrile + H2O
phenylacetic acid + NH3
show the reaction diagram
-
-
-
?
phenylpropionitrile + H2O
phenylpropionic acid + NH3
show the reaction diagram
potassium cyanide + H2O
potassium carbonate + NH3
show the reaction diagram
-
-
-
?
propionitrile + H2O
propionic acid + NH3
show the reaction diagram
pyrazinecarbonitrile + H2O
?
show the reaction diagram
-
32.7% activity compared to 3-cyanopyridine
-
-
?
R(+)-mandelonitrile + H2O
?
show the reaction diagram
316% substrate conversion compared to benzonitrile
-
-
?
ricinine + H2O
?
show the reaction diagram
-
-
-
-
?
succinonitrile + 2 H2O
succinic acid + NH3
show the reaction diagram
-
-
-
-
?
succinonitrile + H2O
succinate + NH3
show the reaction diagram
-
low activity
-
?
succinonitrile + H2O
succinic acid + NH3
show the reaction diagram
thiophen-2-acetonitrile + H2O
thiophen-2-ylacetic acid + NH3
show the reaction diagram
-
56.1% activity compared to benzonitrile
-
-
?
trans-3-pentenenitrile + H2O
trans-3-pentenoic acid + NH3
show the reaction diagram
-
-
-
?
trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile + H2O
trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylic acid + NH3
show the reaction diagram
trichloroacetonitrile + 2 H2O
trichloroacetate + NH3
show the reaction diagram
-
-
-
?
valeronitrile + 2 H2O
valeric acid + NH3
show the reaction diagram
-
-
-
-
?
valeronitrile + H2O
valeric acid + NH3
show the reaction diagram
additional information
?
-