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3.5.5.1: nitrilase

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

Word Map on EC 3.5.5.1

Reaction

A nitrile
+ 2 H2O =
a carboxylate
+
NH3

Synonyms

3-cyanopyridinase, acetonitrilase, Arylacetonitrilase, auxin-producing nitrilase, benzonitrilase, benzonitrilase A, benzonitrilase B, bll6402, BrNIT-T, CrNIT1, CrNIT2, cyc705, CynD, humanNIT1, More, nirilase II, NIT, NIT-T2, Nit06, NIT1, Nit1 nitrilase, Nit102, NIT2, NIT3, NIT4A/B1, NIT4A/B2, NitA, NitAk1, nitmc-fb, NitraS-ATII, nitrilase, nitrilase 1, nitrilase AtNIT1, nitrilase bll6402, nitrilase I, nitrile hydratase/amidase, Nlase, PaCNit, SsAH, SSO2122

ECTree

     3 Hydrolases
         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
             3.5.5 In nitriles
                3.5.5.1 nitrilase

Substrates Products

Substrates Products on EC 3.5.5.1 - nitrilase

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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
2-(methylthio)acetic acid + NH3
show the reaction diagram
-
-
-
?
(phenylthio)acetonitrile + H2O
2-(phenylthio)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
(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
1,2-phenylenediacetic acid + NH3
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
-
-
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
show the reaction diagram
-
-
-
?
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
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic 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-cyanocyclohexaneacetonitrile + H2O
1-cyanocyclohexaneacetic acid + NH3
show the reaction diagram
-
-
-
?
1-[(4-methylphenyl)sulfonyl]piperidine-4-carbonitrile + H2O
?
show the reaction diagram
2 (R,S)-mandelonitrile + 2 H2O
(R)-(-)-mandelic acid + (S)-mandelonitrile
show the reaction diagram
2 (R,S)-mandelonitrile + 4 H2O
(R)-mandelic acid + NH3 + (S)-mandelonitrile
show the reaction diagram
2 2-phenylacetonitrile + 3 H2O
phenylacetic acid + 2-phenylacetamide + NH3
show the reaction diagram
2 2-phenylpropionitrile + 3 H2O
2-phenylpropanoic acid + 2-phenylpropanamide + NH3
show the reaction diagram
2 benzonitrile + 3 H2O
benzoic acid + benzamide + NH3
show the reaction diagram
-
100% activity
-
-
?
2 phenylacetonitrile + 3 H2O
phenylacetamide + phenylacetate + NH3
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-amino-benzonitrile + H2O
2-aminobenzoic acid + NH3
show the reaction diagram
-
88% of the activity as compared to acetonitrile
-
-
?
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-chlorobenzonitrile + H2O
2-chlorobenzoic acid + NH3
show the reaction diagram
-
1% of the activity compared to 2-cyanopyridine
-
-
?
2-chloromandelonitrile + 2 H2O
2-chloromandelic acid + NH3
show the reaction diagram
2-chloromandelonitrile + H2O
2-chloromandelic acid + NH3
show the reaction diagram
-
-
-
?
2-chloromandelonitrile + H2O
?
show the reaction diagram
2-chlorophenylacetonitrile + H2O
?
show the reaction diagram
-
38% of the activity as compared to benzoylacetonitrile
-
-
?
2-cyanophenyl acetonitrile + H2O
?
show the reaction diagram
-
-
-
?
2-cyanopyrazine + H2O
pyrazine-2-carboxylic acid + NH3
show the reaction diagram
-
-
-
-
?
2-cyanopyridine + 2 H2O
2-pyridine carboxylic acid + NH3
show the reaction diagram
2-cyanopyridine + 2 H2O
2-pyridinecarboxylic acid + NH3
show the reaction diagram
-
7% activity compared to benzonitrile
-
-
?
2-cyanopyridine + 2 H2O
picolinic acid + NH3
show the reaction diagram
-
-
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
show the reaction diagram
2-cyanopyridine + 2 H2O
pyridine-2-carboxylic acid + NH3
show the reaction diagram
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 + 2 H2O
4-cyanopentanoic acid + NH3
show the reaction diagram
2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
show the reaction diagram
-
9% of the activity compared to 2-cyanopyridine
-
-
?
2-methylglutaronitrile + H2O
? + NH3
show the reaction diagram
-
-
-
-
?
2-nitrobenzonitrile + H2O
2-nitrobenzoic acid + NH3
show the reaction diagram
-
strain NCIB11215
-
-
?
2-phenylacetonitrile + 2 H2O
2-phenylacetic acid + NH3
show the reaction diagram
-
10.8% activity compared to benzonitrile
-
-
?
2-phenylacetonitrile + 2 H2O
phenylacetate + NH3
show the reaction diagram
-
substrate for isozyme complex NIT4A/B2
-
-
?
2-phenylglycinonitrile + 2 H2O
amino(phenyl)acetic acid + NH3
show the reaction diagram
-
-
-
?
2-phenylpropionitrile + 2 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-(2-chlorophenyl)pentanedinitrile + H2O
(3S)-3-(2-chlorophenyl)-4-cyanobutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 5.1fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 74% enantiomeric excess by wild-type enzyme and with 97% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(3-chlorophenyl)pentanedinitrile + H2O
(3S)-3-(3-chlorophenyl)-4-cyanobutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 3.1fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 93% enantiomeric excess by wild-type enzyme and with 98% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-bromophenyl)pentanedinitrile + H2O
(3S)-3-(4-bromophenyl)-4-cyanobutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 18.6fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 97% enantiomeric excess by wild-type enzyme and with more than 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-chlorophenyl)-3-hydroxypropanenitrile + H2O
(S)-3-(4-chlorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(4-chlorophenyl)pentanedinitrile + H2O
(3S)-3-(4-chlorophenyl)-4-cyanobutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 11.0fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 97% enantiomeric excess by wild-type enzyme and with 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-fluorophenyl)-3-hydroxypropanenitrile + H2O
(S)-3-(4-fluorophenyl)-3-hydroxypropanoic acid + NH3
show the reaction diagram
3-(4-fluorophenyl)pentanedinitrile + H2O
(3S)-4-cyano-3-(4-fluorophenyl)butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 8.8fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 99% enantiomeric excess by wild-type enzyme and with more than 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-hydroxyphenyl)pentanedinitrile + H2O
(3S)-4-cyano-3-(4-hydroxyphenyl)butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 78fold higher than activity of wild-type enzyme
-
-
?
3-(4-hydroxyphenyl)propanenitrile + H2O
3-(4-hydroxyphenyl)propanoic acid + NH3
show the reaction diagram
-
-
-
-
?
3-(4-methoxyphenyl)pentanedinitrile + H2O
(3S)-4-cyano-3-(4-methoxyphenyl)butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 12.8fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 98% enantiomeric excess by wild-type enzyme and with more than 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-methylphenyl)pentanedinitrile + H2O
(3S)-4-cyano-3-(4-methylphenyl)butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 6.7fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 98% enantiomeric excess by wild-type enzyme and with 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-(4-tert-butylphenyl)pentanedinitrile + H2O
(3S)-3-(4-tert-butylphenyl)-4-cyanobutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is2.3fold higher than activity of wild-type enzyme
-
-
?
3-aminobenzonitrile + H2O
3-aminobenzoic acid + NH3
show the reaction diagram
3-aminobutyronitrile + H2O
3-aminobutyric acid + NH3
show the reaction diagram
201% of the activity compared to benzonitrile
-
-
?
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-butenenitrile + H2O
3-butenoic acid + NH3
show the reaction diagram
the enzyme displays a relatively high degree of specificity for 3-butenenitrile. Helical twist and substrate size correlate and when binding pocket residues are exchanged between two nitrilases that show the same twist but different specificities, their specificities change. It is proposed that helical twist influences the overall size of the binding pocket
-
-
?
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-chlorobenzoylacetonitrile + H2O
?
show the reaction diagram
-
43% of the activity as compared to benzoylacetonitrile
-
-
?
3-chloromandelonitrile + H2O
3-chloromandelic acid + NH3
show the reaction diagram
-
-
-
?
3-cyanobenzonitrile + H2O
3-cyanobenzoic acid + NH3
show the reaction diagram
-
-
-
-
?
3-cyanopyridine + 2 H2O
3-pyridinecarboxylic acid + NH3
show the reaction diagram
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 + 2 H2O
pyridine-3-carboxylic acid + NH3
show the reaction diagram
3-cyanopyridine + H2O
pyridine 3-carboxylic acid + NH3
show the reaction diagram
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 + 2 H2O
(R)-3-hydroxy-4-cyanobutanoic acid + NH3
show the reaction diagram
-
-
-
-
?
3-hydroxyglutaronitrile + 4 H2O
3-hydroxyglutaric acid + 2 NH3
show the reaction diagram
activity is 1.15% compared to activity with iminodiacetonitrile
-
-
?
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-methoxylbenzoylacetonitrile + H2O
?
show the reaction diagram
-
38% of the activity as compared to benzoylacetonitrile
-
-
?
3-methylbenzonitrile + H2O
3-methylbenzoic acid + NH3
show the reaction diagram
3-nitrobenzonitrile + H2O
3-nitrobenzoic acid + NH3
show the reaction diagram
3-phenylpentanedinitrile + H2O
(3S)-4-cyano-3-phenylbutanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 5.8fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 96% enantiomeric excess by wild-type enzyme and with 96% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-phenylpropanenitrile + H2O
phenylacetic acid + NH3
show the reaction diagram
3-phenylpropionitrile + H2O
3-phenylpropanoate + NH3
show the reaction diagram
activity is 7.24% compared to activity with iminodiacetonitrile
-
-
?
3-phenylpropionitrile + H2O
3-phenylpropionate + NH3
show the reaction diagram
151% of the activity compared to benzonitrile
-
-
?
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
3-[4-(dimethylamino)phenyl]pentanedinitrile + H2O
(3S)-4-cyano-3-[4-(dimethylamino)phenyl]butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 28.0fold higher than activity of wild-type enzyme
-
-
?
3-[4-(methylsulfanyl)phenyl]pentanedinitrile + H2O
(3S)-4-cyano-3-[4-(methylsulfanyl)phenyl]butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 18.0fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 97% enantiomeric excess by wild-type enzyme and with more than 99% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-[4-(propan-2-yl)phenyl]pentanedinitrile + H2O
(3S)-4-cyano-3-[4-(propan-2-yl)phenyl]butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 18.0fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 95% enantiomeric excess by wild-type enzyme and with 98% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
3-[4-(trifluoromethyl)phenyl]pentanedinitrile + H2O
(3S)-4-cyano-3-[4-(trifluoromethyl)phenyl]butanoic acid
show the reaction diagram
the specific activity of mutant enzyme P194A/I201A/F202V is 4.8fold higher than activity of wild-type enzyme The S-enantiomer ist formed with 97% enantiomeric excess by wild-type enzyme and with 96% enantiomeric excess by the mutant enzyme P194A/I201A/F202V
-
-
?
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-aminobutyronitrile + H2O
4-aminobutyric acid + NH3
show the reaction diagram
251% of the activity compared to benzonitrile
-
-
?
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-chlorobenzoylacetonitrile + H2O
?
show the reaction diagram
-
16% of the activity as compared to benzoylacetonitrile
-
-
?
4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
show the reaction diagram
4-chlorobutyronitrile + H2O
4-chlorobutyric acid + NH3
show the reaction diagram
4-chloromandelonitrile + H2O
3-chloromandelic acid + NH3
show the reaction diagram
-
-
-
?
4-cyanophenyl acetonitrile + H2O
?
show the reaction diagram
-
-
-
?
4-cyanopyridine + 2 H2O
4-pyridinecarboxylic acid + NH3
show the reaction diagram
4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
show the reaction diagram
4-cyanopyridine + 2 H2O
pyridine-4-carboxylic acid + NH3
show the reaction diagram
4-cyanopyridine + H2O
pyridine 4-carboxylic acid + NH3
show the reaction diagram
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
acetamide + H2O
acetate + NH3
show the reaction diagram
-
119% of the activity as compared to acetonitrile
-
-
?
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
acrylamide + H2O
acrylic acid + NH3
show the reaction diagram
-
101% of the activity as compared to acetonitrile
-
-
?
acrylonitrile + 2 H2O
acrylic acid + NH3
show the reaction diagram
acrylonitrile + H2O
acrylate + NH3
show the reaction diagram
400% of the activity compared to benzonitrile
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
show the reaction diagram
adiponitrile + 2 H2O
adipic acid + 2 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
2-cyano-2-methylpropanoic 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
about 30% activity compared to acrylonitrile
-
-
?
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
benzonitrile + 2 H2O
benzoate + NH3
show the reaction diagram
benzonitrile + 2 H2O
benzoic acid + NH3
show the reaction diagram
benzoylacetonitrile + H2O
?
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
-
-
?
bis-acrylamide + H2O
?
show the reaction diagram
-
67% of the activity as compared to acetonitrile
-
-
?
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
butyrate + NH3
show the reaction diagram
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
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 + 2 H2O
crotonic acid + NH3
show the reaction diagram
crotononitrile + H2O
?
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
-
-
?
di-phenylacetonitrile + H2O
? + NH3
show the reaction diagram
72% of the activity compared to benzonitrile
-
-
?
dicyanobutane + H2O
? + NH3
show the reaction diagram
-
-
-
-
?
dicyanooctane + H2O
? + NH3
show the reaction diagram
-
-
-
-
?
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
-
-
-
?
dodecanenitrile + H2O
dodecanoic acid + NH3
show the reaction diagram
-
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
show the reaction diagram
glutaronitrile + H2O
? + NH3
show the reaction diagram
319% of the activity compared to benzonitrile
-
-
?
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
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 + 2 NH3
show the reaction diagram
iminodiacetonitrile + H2O
iminodiacetic acid + NH3
show the reaction diagram
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
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
mandelate + NH3
show the reaction diagram
-
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
show the reaction diagram
mandelonitrile + H2O
?
show the reaction diagram
mandelonitrile + H2O
? + NH3
show the reaction diagram
69% of the activity compared to benzonitrile
-
-
?
mandelonitrile + H2O
mandelic acid + NH3
show the reaction diagram
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-methyl-propionamide + H2O
?
show the reaction diagram
-
161% of the activity as compared to acetonitrile
-
-
?
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
-
-
?
pentanenitrile + H2O
pentanoic acid + NH3
show the reaction diagram
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
show the reaction diagram
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
show the reaction diagram
phenylacetonitrile + H2O
?
show the reaction diagram
phenylbutyronitrile + H2O
phenylbutyric acid + NH3
show the reaction diagram
phenylenediacetonitrile + H2O
? + NH3
show the reaction diagram
-
-
-
-
?
phenylglycinenitrile + 2 H2O
phenylglycine + NH3
show the reaction diagram
-
-
-
?
phenylglycinonitrile + H2O
phenylglycine + NH3
show the reaction diagram
phenylpropionitrile + 2 H2O
phenylpropionic acid + NH3
show the reaction diagram
potassium cyanide + H2O
potassium carbonate + NH3
show the reaction diagram
propionitrile + H2O
propionate + 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
-
-
?
pyridine + H2O
?
show the reaction diagram
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
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
-
-
?
thiophene + H2O
? + NH3
show the reaction diagram
-
-
-
-
?
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
?
-