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Information on EC 3.5.5.7 - Aliphatic nitrilase
for references in articles please use BRENDA:EC3.5.5.7
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EC Tree 3 Hydrolases
3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
3.5.5 In nitriles
3.5.5.7 Aliphatic nitrilase
IUBMB Comments
Preferentially hydrolyses aliphatic nitriles, some of which are apparently not substrates for other known nitrilases (EC 3.5.5.1). Substrates include crotononitrile, acrylonitrile and glutaronitrile.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 3.5.5.7
- rhodococcus
-
enantioselectivity
- erythropolis
- synthesis
-
dinitriles
- acetamide
- rhodochrous
- industry
-
mononitriles
- microbacterium
-
arylaliphatic
-
nitrile-degrading
- environmental protection
- biotechnology
showSynonyms
nitrile hydratase/amidase, aliphatic nitrilase, nitpf5, pacnit, reh16, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BjNIT3397
NitA
nitC1
nitC2
NitPf5
nitrilase
nitrile hydratase/amidase
PaCNit
additional information
additional information
the enzyme belongs to branch 1.4 of the superfamily of nitrilases, overview
additional information
-
Candida guilliermondii is the teleomorph of Pichia guilliermondii NRRL Y-2075
additional information
-
Candida guilliermondii is the teleomorph of Pichia guilliermondii NRRL Y-2075
-
additional information
the enzyme belongs to the superfamily of nitrilases, branch 1.2 aliphatic nitrilases, overview
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
R-CN + 2 H2O = R-COOH + NH3
-
-
-
-
R-CN + 2 H2O = R-COOH + NH3
enzyme structure and reaction mechanism
R-CN + 2 H2O = R-COOH + NH3
enzyme structure, covalent mechanism, formation of an enzyme-thioimidate intermediate rather than addition of water to the nitrile
R-CN + 2 H2O = R-COOH + NH3
preferentially hydrolyses aliphatic nitriles, some of which are apparently not substrates for other known nitrilases, EC 3.5.5.1. Substrates include crotonitrile, acrylnitrile and glutaronitrile
-
R-CN + 2 H2O = R-COOH + NH3
hydrolysis of substrates probably involves the conjugated pi-electron system of the aromatic ring of substrate or Tyr-142 as an electron acceptor
R-CN + 2 H2O = R-COOH + NH3
preferentially hydrolyses aliphatic nitriles, some of which are apparently not substrates for other known nitrilases, EC 3.5.5.1. Substrates include crotonitrile, acrylnitrile and glutaronitrile
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of C-N bond
hydrolysis of nitriles
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
acrylonitrile degradation II
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SYSTEMATIC NAME
IUBMB Comments
Aliphatic nitrile aminohydrolase
Preferentially hydrolyses aliphatic nitriles, some of which are apparently not substrates for other known nitrilases (EC 3.5.5.1). Substrates include crotononitrile, acrylonitrile and glutaronitrile.
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CAS REGISTRY NUMBER
COMMENTARY
143236-44-6
Nitrilase (Rhodococcus rhodochrous clone pNK20)
9024-90-2
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,4-dicyano-2-butene + H2O
?
-
Substrates: 42.6% of the activity with crotononitrile
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1,4-dicyanobutane + H2O
?
Substrates: 114.3% activity compared to 3-cyanopyridine
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?
1,8-dicyanooctane + H2O
?
Substrates: 114.3% activity compared to 3-cyanopyridine
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?
1-cyclohexeneacetonitrile + H2O
1-cyclohexene carboxylate + NH3
-
Substrates: 18.2% of the activity with crotononitrile
Products: -
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?
1-cyclopenteneacetonitrile + H2O
1-cyclopentene carboxylate + NH3
-
Substrates: 24.9% of the activity with crotononitrile
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?
2 fumarodinitrile + 3 H2O
3-cyanoacrylamide + 3-cyanoacrylic acid + NH3
Substrates: 11% compared to the activity with 3-hexenedinitrile. Fumarodinitrile is converted to the monocarboxylate and the monocarboxamide in a ratio of about 65:35
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?
2,4-dicyano-1-butene + H2O
?
-
Substrates: 127% of the activity with crotononitrile
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?
2-butenenitrile + H2O
2-butenic acid + NH3
Substrates: worst substrate
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?
2-chloroacrylonitrile + H2O
2-chloroacrylic acid + NH3
-
Substrates: 47.1% of the activity with crotononitrile
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?
2-chloropropionitrile + 2 H2O
2-chloropropionic acid + NH3
Substrates: 86% compared to the activity with 3-hexenedinitrile
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?
2-cyanopyridine + 2 H2O
2-pyridine carboxylic acid + NH3
Substrates: -
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?
2-furonitrile + H2O
furoic acid + NH3
-
Substrates: 52.0% of the activity with crotononitrile
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?
2-hydroxy-3-butenenitrile + 2 H2O
2-hydroxybut-3-enoic acid + NH3
Substrates: 8% compared to the activity with 3-hexenedinitrile
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?
2-hydroxybutyronitrile + H2O
2-hydroxybutyrate + NH3
Substrates: 3% compared to the activity with 3-hexenedinitrile
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?
2-methyl-2-butenenitrile + H2O
2-methyl-2-butenoic acid + NH3
-
Substrates: 14.9% of the activity with crotononitrile
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?
2-methyl-3-butenenitrile + 2 H2O
2-methyl-but-3-enoic acid + NH3
Substrates: 3% compared to the activity with 3-hexenedinitrile
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?
2-methyl-3-butenenitrile + H2O
2-methyl-3-butenoic acid + NH3
-
Substrates: 46.8% of the activity with crotononitrile
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?
2-methyleneglutarodinitrile + H2O
? + NH3
Substrates: 11% compared to the activity with 3-hexenedinitrile. 2-Methyleneglutarodinitrile is mainly converted to the corresponding monocarboxylic acid , but also some traces of the monoamide are formed
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?
2-methylglutaronitrile + 4 H2O
2-methylglutarate + 2 NH3
Substrates: 23.3% activity compared to 3-cyanopyridine
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?
2-pentenenitrile + H2O
2-pentenoic acid + NH3
-
Substrates: 6.33% of the activity with crotononitrile
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?
2-phenylbutyronitrile + 2 H2O
2-phenylpropionic acid + NH3
-
Substrates: activity is 11% compared to activity with 3-cyanopyridine
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?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
Substrates: -
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?
2-thiopheneacetonitrile + H2O
thiophene-2-carboxylate + NH3
-
Substrates: 73.5% of the activity with crotononitrile
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?
2-thiophenecarbonitrile + H2O
2-thiophenecarboxylate + NH3
-
Substrates: 61.1% of the activity with crotononitrile
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?
3,3'-oxydipropionitrile + H2O
? + NH3
-
Substrates: 29.0% of the activity with crotononitrile
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?
3-aminobutyronitrile + H2O
3-aminobutyric acid + NH3
Substrates: 201% activity compared to benzonitrile
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?
3-chloropropionitrile + H2O
3-chloropropanoate + NH3
-
Substrates: 113% of the activity with crotononitrile
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?
3-ethoxybenzonitrile + H2O
3-ethoxybenzoate + NH3
-
Substrates: 21.1% of the activity with crotononitrile
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?
3-hydroxyglutaronitrile + 4 H2O
3-hydroxyglutaric acid + 2 NH3
-
Substrates: activity is 38% compared to activity with 3-cyanopyridine
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?
3-hydroxypropionitrile + 2 H2O
3-hydroxypropionitrile + NH3
-
Substrates: activity is 1.5fold higher compared to activity with 3-cyanopyridine
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?
3-methoxybenzonitrile
3-methoxybenzoate + NH3
-
Substrates: 24.8% of the activity with crotononitrile
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?
3-nitrobenzonitrile + H2O
3-nitrobenzoate + NH3
-
Substrates: 74.5% of the activity with crotononitrile
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?
3-nitrobenzonitrile + H2O
3-nitrobenzoic acid + NH3
Substrates: 110% activity compared to benzonitrile
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?
3-pentenenitrile + H2O
3-pentenoic acid + NH3
-
Substrates: 132% of the activity with crotononitrile
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?
3-phenylpropionitrile + H2O
3-phenylpropanoate + NH3
Substrates: 147.3% activity compared to 3-cyanopyridine
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?
3-phenylpropionitrile + H2O
?
Substrates: 59% activity compared to glutaronitrile
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?
3-thiopheneacetonitrile + H2O
thiophene-3-carboxylate + NH3
-
Substrates: 66.3% of the activity with crotononitrile
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?
3-tolunitrile + H2O
3-methylbenzenecarboxylic acid + NH3
-
Substrates: 67.9% of the activity with crotononitrile
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?
3-xylylene dicyanide + H2O
?
-
Substrates: 14.62% of the activity with crotononitrile
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?
4-aminobenzonitrile + 2 H2O
4-aminobenzoic acid + NH3
Substrates: 57.6% compared to the activity with 3-cyanopyridine
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?
4-aminobutyronitrile + H2O
4-aminobutyric acid + NH3
Substrates: 251% activity compared to benzonitrile
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?
4-chlorobutyronitrile + 2 H2O
4-chlorobutyric acid + NH3
-
Substrates: activity is 1.49fold higher compared to activity with 3-cyanopyridine
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?
4-cyano-1-cyclohexene + H2O
1-cyclohexene-4-carboxylate + NH3
-
Substrates: 7.03% of the activity with crotononitrile
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?
4-cyanopyridine + H2O
4-carboxypyridine + NH3
-
Substrates: 9.71% of the activity with crotononitrile
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?
4-nitrobenzonitrile + H2O
4-nitrobenzoic acid + NH3
Substrates: 151% activity compared to benzonitrile
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?
acetonitrile + 2 H2O
acetic acid + NH3
Substrates: 19.1% compared to the activity with 3-cyanopyridine
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?
acetonitrile + H2O
?
Substrates: 5% activity compared to glutaronitrile
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?
allylcyanide + 2 H2O
but-3-enoic acid + NH3
Substrates: 12% compared to the activity with 3-hexenedinitrile
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?
beta-cyano-L-alanine + H2O
asparagine + aspartic acid
Substrates: -
Products: 60:40 mixture
Products: 60:40 mixture
?
butyronitrile + H2O
?
Substrates: 6% activity compared to glutaronitrile
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?
capronitrile + H2O
hexanoate + NH3
-
Substrates: 38.7% of the activity with crotononitrile
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?
chloroacetonitrile + H2O
chloroacetate + NH3
-
Substrates: 61.7% of the activity with crotononitrile
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?
cinnamonitrile + 2 H2O
cinnamic acid + NH3
-
Substrates: activity is 8fold higher compared to activity with 3-cyanopyridine
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?
crotonitrile + H2O
?
Substrates: 7% activity compared to glutaronitrile
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?
cyano-5-valeramide + H2O
glutaric acid 5-amide + NH3
-
Substrates: at 28% of the activity with adiponitrile
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?
cyano-5-valeric acid + H2O + H2O
?
-
Substrates: at 28% of the activity with adiponitrile
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?
cyanoacetic acid ethyl ester + H2O
acetic acid ethyl ester + NH3
-
Substrates: 117% of the activity withcrotononitrile
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?
cyanopyrazine + H2O
pyrazine-2-carboxylate + NH3
-
Substrates: 17.3% of the activity with crotononitrile
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?
cyclopentanecarbonitrile + H2O
cyclopentanoic acid + NH3
-
Substrates: 11.7% of the activity with crotononitrile
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?
cyclopentanocarbonitrile + H2O
cyclopentanocarbonate + NH3
-
Substrates: -
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?
cyclopropanecarbonitrile + H2O
cyclopropanoic acid + NH3
-
Substrates: 22.9% of the activity with crotononitrile
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?
diaminomaleonitrile + H2O
diaminomaleic acid + NH3
-
Substrates: 18.6% of the activity with crotononitrile
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?
dimethylaminopropionitrile + 2 H2O
dimethylaminopropionic acid + NH3
Substrates: 50.5% compared to the activity with 3-cyanopyridine
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?
dimethylmalononitrile + H2O
dimethylmalonic acid + NH3
-
Substrates: -
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?
diphenylacetonitrile + H2O
diphenylacetic acid + NH3
Substrates: 72% activity compared to benzonitrile
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?
dodecanenitrile + 2 H2O
dodecanoic acid + NH3
-
Substrates: activity is 2.46fold higher as compared to activity with 3-cyanopyridine
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?
dodecanenitrile + H2O
dodecanoate + NH3
Substrates: 13.5% activity compared to 3-cyanopyridine
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?
hexanedinitrile + 2 H2O
?
Substrates: 111% compared to the activity with 3-cyanopyridine
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?
hydrocinnamonitrile + H2O
hydrocinnamic acid + NH3
-
Substrates: -
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?
iminodiacetonitrile + 2 H2O
iminodiacetic acid + NH3
-
Substrates: activity is 2.34fold higher as compared to activity with 3-cyanopyridine
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?
iminodiacetonitrile + 4 H2O
iminodiacetic acid + 2 NH3
-
Substrates: activity is 39% compared to activity with 3-cyanopyridine
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?
indole-3-acetonitrile + 2 H2O
indol-3-acetic acid + NH3
-
Substrates: activity is 48% compared to activity with 3-cyanopyridine
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?
isobutyronitrile + H2O
isobutyric acid + NH3
-
Substrates: -
Products: -
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?
isocapronitrile + H2O
isohexanoate + NH3
-
Substrates: 41.5% of the activity with crotononitrile
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?
isophthalonitrile + H2O
isophthalate + NH3
-
Substrates: 66.1% of the activity with crotononitrile
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?
m-tolunitrile + H2O
m-methylbenzoate + NH3
Substrates: -
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?
malononitrile + 2 H2O
malonic acid + NH3
Substrates: 120.5% compared to the activity with 3-cyanopyridine
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?
metacrylonitrile + H2O
metacrylic acid + NH3
-
Substrates: -
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?
methoxyacetonitrile + H2O
methoxyacetate + NH3
-
Substrates: 37.4% of the activity with crotononitrile
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?
N-methyl-beta-alaninenitrile + H2O
N-methyl-beta-Ala + NH3
-
Substrates: 11.4% of the activity with crotononitrile
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?
pentanenitrile + H2O
pentanoate + NH3
Substrates: 62% activity compared to 3-cyanopyridine
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?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
Substrates: 27.3% of the activity with crotononitrile
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?
pimelonitrile + 4 H2O
pimelic acid + 2 NH3
-
Substrates: activity is 85% compared to activity with 3-cyanopyridine
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pimelonitrile + H2O
pimelic acid + NH3
-
Substrates: 27.3% of the activity with crotononitrile
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piperonylonitrile + H2O
(3,4-methylenedioxy)benzoate + NH3
-
Substrates: 6.8% of the activity with crotononitrile
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?
propionitrile + 2 H2O
propionic acid + NH3
Substrates: 33.2% compared to the activity with 3-cyanopyridine
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?
propionitrile + H2O
?
Substrates: 5% activity compared to glutaronitrile
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?
R-CN + H2O
R-COOH + NH3
-
Substrates: enzyme uses both aliphatic and aromatic nitriles, no formation of amide intermediate
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?
suberonitrile + H2O
decanedioic acid + NH3
-
Substrates: 21.4% of the activity with crotononitrile
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succinonitrile + 2 H2O
succinic acid + NH3
Substrates: 137.7% compared to the activity with 3-cyanopyridine
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thiophene-3-carbonitrile + 2 H2O
thiophene-3-carboxylic acid + NH3
-
Substrates: activity is 2.42fold higher as compared to activity with 3-cyanopyridine
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?
thiophene-3-carbonitrile + H2O
?
Substrates: 51.2% activity compared to 3-cyanopyridine
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valeronitrile + 2 H2O
valeric acid + NH3
-
Substrates: activity is 99% compared to activity with 3-cyanopyridine
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valeronitrile + H2O
pentanoate + NH3
-
Substrates: 40.8% of the activity with crotononitrile
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(E)-2-methyl-2-butenenitrile + H2O
(E)-2-methyl-2-butenoic acid + NH3
-
Substrates: regioselective hydrolysis, no detectable conversion of (Z)-2-methyl-2-butenenitrile
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(E)-2-methyl-2-butenenitrile + H2O
(E)-2-methyl-2-butenoic acid + NH3
-
Substrates: regioselective hydrolysis, no detectable conversion of (Z)-2-methyl-2-butenenitrile
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2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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?
2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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2,6-dichlorobenzonitrile + H2O
2,6-dichlorobenzamide + ?
-
Substrates: -
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2-aminocrotononitrile + H2O
2-aminocrotonic acid + NH3
-
Substrates: 30.3% of the activity with crotononitrile
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2-aminocrotononitrile + H2O
2-aminocrotonic acid + NH3
-
Substrates: 30.3% of the activity with crotononitrile
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2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
Substrates: activity is 3.35fold higher compared to activity with 3-cyanopyridine
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2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
Substrates: 110% activity compared to benzonitrile
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?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
Substrates: low activity
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2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
Substrates: second best substrate
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2-methylglutaronitrile + 2 H2O
4-cyanopentanoic acid + NH3
-
Substrates: activity is 10% compared to activity with 3-cyanopyridine
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2-methylglutaronitrile + 2 H2O
4-cyanopentanoic acid + NH3
Substrates: 77% activity compared to glutaronitrile
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2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
-
Substrates: activity is 2.3fold higher as compared to activity with 3-cyanopyridine
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2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
-
Substrates: activity is 2.3fold higher as compared to activity with 3-cyanopyridine
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2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
-
Substrates: -
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3-aminopropionitrile + 2 H2O
beta-alanine + NH3
-
Substrates: the enzyme catalyzes the hydrolysis of 3-aminopropionitrile at high substrate concentration up to 3 M. With the increase of substrate concentration, 3-aminopropanamide is formed, reaching 33% at the substrate concentration of 3 M
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3-aminopropionitrile + 2 H2O
beta-alanine + NH3
-
Substrates: the enzyme catalyzes the hydrolysis of 3-aminopropionitrile at high substrate concentration up to 3 M. With the increase of substrate concentration, 3-aminopropanamide is formed, reaching 33% at the substrate concentration of 3 M
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3-cyanopyridine + 2 H2O
nicotinic acid + NH3
Substrates: -
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3-cyanopyridine + 2 H2O
nicotinic acid + NH3
Substrates: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
Substrates: 100% activity
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
Cereibacter sphaeroides LHS-305
Substrates: 100% activity
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
Substrates: -
Products: -
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?
3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
Substrates: 151% activity compared to benzonitrile
Products: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
Substrates: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
Substrates: -
Products: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
Substrates: -
Products: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
Substrates: -
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3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
Substrates: -
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3-cyanopyridine + H2O
3-carboxypyridine + NH3
-
Substrates: 7.72% of the activity with crotononitrile
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3-cyanopyridine + H2O
3-carboxypyridine + NH3
Substrates: 11% activity compared to glutaronitrile
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3-ethoxyacrylonitrile + H2O
3-ethoxyacrylic acid + NH3
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Substrates: 19.1% of the activity with crotononitrile
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3-ethoxyacrylonitrile + H2O
3-ethoxyacrylic acid + NH3
-
Substrates: 19.1% of the activity with crotononitrile
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3-phenylpropionitrile + 2 H2O
3-phenylpropionic acid + NH3
-
Substrates: activity is 61% compared to activity with 3-cyanopyridine
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3-phenylpropionitrile + 2 H2O
3-phenylpropionic acid + NH3
-
Substrates: activity is 2.15fold higher as compared to activity with 3-cyanopyridine
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3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
Substrates: 151% activity compared to benzonitrile
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3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
Substrates: 151% activity compared to benzonitrile
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4-chlorobutyronitrile + 2 H2O
4-chlorobutanoic acid + NH3
-
Substrates: activity is 2.44fold higher as compared to activity with 3-cyanopyridine
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4-chlorobutyronitrile + 2 H2O
4-chlorobutanoic acid + NH3
Substrates: 66.7% compared to the activity with 3-cyanopyridine
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4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
Substrates: 135% activity compared to 3-cyanopyridine
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4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
Cereibacter sphaeroides LHS-305
Substrates: 135% activity compared to 3-cyanopyridine
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4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
-
Substrates: 116% of the activity with crotononitrile
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4-cyanopyridine + 2 H2O
4-pyridinecarboxylic acid + NH3
-
Substrates: 50% of the activity with acrylonitrile
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4-cyanopyridine + 2 H2O
4-pyridinecarboxylic acid + NH3
-
Substrates: 50% of the activity with acrylonitrile
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4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
-
Substrates: activity is 3fold higher compared to activity with 3-cyanopyridine
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4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
Substrates: 225% activity compared to benzonitrile
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4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
-
Substrates: low activity
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acetonitrile + H2O
acetate + NH3
Substrates: 135% activity compared to benzonitrile
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acetonitrile + H2O
acetate + NH3
Substrates: 135% activity compared to benzonitrile
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acetonitrile + H2O
acetate + NH3
-
Substrates: -
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acetonitrile + H2O
acetate + NH3
-
Substrates: 28.3% of the activity with crotononitrile
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