Any feedback?
No. of entries
Information on EC 3.5.5.5 - Arylacetonitrilase
for references in articles please use BRENDA:EC3.5.5.5
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree 3 Hydrolases
3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
3.5.5 In nitriles
3.5.5.5 Arylacetonitrilase
IUBMB Comments
Requires thiol compounds. Also hydrolyses other 4-substituted phenylacetonitriles, thien-2-ylacetonitrile, tolylacetonitriles, and, more slowly, benzyl cyanide.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 3.5.5.5
- mandelonitrile
-
enantioselectivity
- fluorescens
- arylacetonitriles
-
enantiomeric
-
s-mandelic
- phenylacetonitrile
- alcaligenes
-
r,s-mandelonitrile
- benzaldehyde
- synthesis
-
arylacetic
- esculenta
-
enantiospecificity
-
ultrafast
- psychrotolerans
-
s-selectivity
-
manihot
- biotechnology
showSynonyms
arylacetonitrilase, gpnor51, nitmp, nitan, nitrilase ppl19, blr3397, enantioselective arylacetonitrilase, arylacetonitrile-hydrolyzing nitrilase, more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Arylacetonitrilase
arylacetonitrile-hydrolyzing nitrilase
arylacetonitrile-specific nitrilase
blr3397
enantioselective arylacetonitrilase
GPnor51
NIT
NitA
NitAd
NitAk2
NitMp
nitrilase
nitrilase PpL19
Nitrilase, arylaceto-
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-chlorophenylacetonitrile + 2 H2O = 4-chlorophenylacetate + NH3
-
-
-
-
4-chlorophenylacetonitrile + 2 H2O = 4-chlorophenylacetate + NH3
reaction mechanism, overview
-
4-chlorophenylacetonitrile + 2 H2O = 4-chlorophenylacetate + NH3
reaction mechanism, overview
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis
hydrolysis of nitriles
hydrolysis of nitriles
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
Arylacetonitrile aminohydrolase
Requires thiol compounds. Also hydrolyses other 4-substituted phenylacetonitriles, thien-2-ylacetonitrile, tolylacetonitriles, and, more slowly, benzyl cyanide.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
132053-06-6
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(2-bromophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 74% activity compared to phenylacetonitrile
Products: -
Products: -
?
(2-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(2-fluorophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 439% activity compared to phenylacetonitrile
Products: -
Products: -
?
(3-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-bromophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 706% activity compared to phenylacetonitrile
Products: -
Products: -
?
(3-chlorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-chlorophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 810% activity compared to phenylacetonitrile
Products: -
Products: -
?
(3-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-fluorophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 454% activity compared to phenylacetonitrile
Products: -
Products: -
?
(4-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-bromophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 680% activity compared to phenylacetonitrile
Products: -
Products: -
?
(4-chlorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-chlorophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 1083% activity compared to phenylacetonitrile
Products: -
Products: -
?
(4-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-fluorophenyl)(hydroxy)acetic acid + NH3
-
Substrates: 891% activity compared to phenylacetonitrile
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)-mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: the enzyme produces up to more than 70 g/l of (R)-mandelic acid (enantiomeric excess 94.5-95.6%) in batch or fed-batch mode. Its volumetric productivities are the highest in batch mode (571 g/l*d) and its catalyst productivities in fed-batch mode (39.9 g/g of dcw)
Products: -
Products: -
?
1,4-dicyanobutane + H2O
adipic acid + NH3
-
Substrates: 47% activity compared to phenylacetonitrile
Products: -
Products: -
?
1-cyclohexenylacetonitrile + H2O
1-cyclohexenylacetate + NH3
-
Substrates: at 3.3% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
2 2-phenylglycinonitrile + 3 H2O
2-phenylglycine + 2-amino-2-phenylacetamide + NH3
-
Substrates: 80% of the activity with mandelonitrile. 35% enantiomeric excess for S-configuration in acid formation, 10.26% of product is amide with 92% enantiomeric excess for S-configuration
Products: -
Products: -
?
2,4-dichlorobenzylcyanide + H2O
2,4-dichlorophenylacetic acid + NH3
-
Substrates: at 6.5% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
2-acetyloxy-2-methylphenylacetonitrile + H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-chlorobenzylcyanide + H2O
2-chlorophenylacetic acid + NH3
-
Substrates: at 6% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
2-chloromandelonitrile + H2O
(R)-2-chloromandelic acid + NH3
-
Substrates: 33.75% activity compared to phenylacetonitrile
Products: enantioselectivity ee 98.2%
Products: enantioselectivity ee 98.2%
?
2-chloromandelonitrile + H2O
2-chloromandelic acid + NH3
-
Substrates: activity is 20% compared to activity with mandelonitrile
Products: -
Products: -
?
2-chlorophenyl acetonitrile + H2O
2-chlorobenzoic acid + NH3
-
Substrates: 76.1% of the activity with mandelonitrile
Products: -
Products: -
ir
2-hydroxy-2-phenylpropionitrile + H2O
2-hydroxy-2-phenylpropionic acid + 2-hydroxy-2-phenylpropionamide + NH3
-
Substrates: i.e. acetophenone cyanohydrin
Products: product ratio of about 3.4:1 for 2-hydroxy-2-phenylpropionic acid and 2-hydroxy-2-phenylpropionamide
Products: product ratio of about 3.4:1 for 2-hydroxy-2-phenylpropionic acid and 2-hydroxy-2-phenylpropionamide
?
2-hydroxy-3-butenenitrile + H2O
2-hydroxy-3-butenoic acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-methoxybenzylcyanide + H2O
2-methoxyphenylacetic acid + NH3
-
Substrates: at 2% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
2-methoxyphenyl acetonitrile + H2O
2-methoxybenzoic acid + NH3
-
Substrates: 44.5% of the activity with mandelonitrile
Products: -
Products: -
ir
2-methyl-2-phenylpropionitrile + H2O
2-methyl-2-phenylpropionic acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-methyleneglutarodinitrile + H2O
? + NH3
Substrates: 11% compared to the activity with 3-hexenedinitrile. 2-Methyleneglutarodinitrile is mainly to the corresponding monocarboxylic, but also some traces of the monoamide are formed
Products: -
Products: -
?
2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
-
Substrates: 0.12% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-methylglutaronitrile + H2O
2-methylglutarate + NH3
-
Substrates: activity is 9.6% compared to activity with mandelonitrile
Products: -
Products: -
?
2-methylglutaronitrile + H2O
? + NH3
-
Substrates: 63% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-phenylbutyronitrile + H2O
2-phenylbutyric acid + NH3
-
Substrates: 0.2% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-phenylglycinonitrile + 2 H2O
2-phenylglycine + NH3
-
Substrates: 3% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-phenylpropionitrile + H2O
2-phenylpropionate + NH3
-
Substrates: low activity, 2% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-phenylpropionitrile + H2O
? + NH3
Substrates: -
Products: -
Products: -
?
2-phenylvaleronitrile + 2 H2O
2-phenylvaleric acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-phenylvaleronitrile + H2O
2-phenylvaleric acid + NH3
-
Substrates: 700% of the activity with mandelonitrile
Products: -
Products: -
?
2-thiophene acetonitrile + H2O
thiophene-2-carboxylic acid + NH3
-
Substrates: 137% of the activity with mandelonitrile
Products: -
Products: -
ir
2-trimethylsilyloxy-2-phenylacetonitrile + H2O
2-trimethylsilyloxy-2-phenylacetic acid + NH3
-
Substrates: 4% activity compared to phenylacetonitrile
Products: -
Products: -
?
3,4-(methylenedioxy)phenylacetonitrile + H2O
3,4-(methylendioxy)phenylacetic acid + NH3
-
Substrates: at 65% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
3,4-dichlorobenzylcyanide + H2O
3,4-dichlorophenylacetic acid + NH3
-
Substrates: at 14% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
3-aminopropionitrile + H2O
3-aminopropanoic acid + NH3
-
Substrates: 7% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-chlorobenzylcyanide + H2O
3-chlorophenylacetic acid + NH3
-
Substrates: at 43% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
Substrates: 43.2% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-hydroxyglutaronitrile + 4 H2O
3-hydroxyglutaric acid + 2 NH3
-
Substrates: 0.12% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-hydroxypropionitrile + H2O
3-hydroxypropanoate + NH3
-
Substrates: 1% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-hydroxypropionitrile + H2O
3-hydroxypropionic acid + NH3
-
Substrates: 0.07% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-indolylacetonitrile + H2O
3-indolylacetic acid + NH3
-
Substrates: 2% activity compared to phenylacetonitrile
Products: -
Products: -
?
3-methoxyphenylacetonitrile + 2 H2O
3-methoxyphenylacetic acid + NH3
-
Substrates: -
Products: -
Products: -
?
4-aminophenyl acetonitrile + H2O
4-aminobenzoic acid + NH3
-
Substrates: 502.3% of the activity with mandelonitrile
Products: -
Products: -
ir
4-chlorobutyronitrile + H2O
4-chlorobutyric acid + NH3
-
Substrates: 0.06% activity compared to phenylacetonitrile
Products: -
Products: -
?
4-chlorophenyl acetonitrile + H2O
4-chlorobenzoic acid + NH3
-
Substrates: 360.3% of the activity with mandelonitrile
Products: -
Products: -
ir
4-cyanopyridine + 2 H2O
4-pyridinecarboxylic acid + NH3
-
Substrates: 512% of the rate with benzonitrile, cell extract
Products: -
Products: -
?
4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
-
Substrates: 142% activity compared to phenylacetonitrile
Products: -
Products: -
?
4-hydroxy benzonitrile + H2O
4-hydroxybenzoate + NH3
-
Substrates: 23.1% of the activity with mandelonitrile
Products: -
Products: -
ir
4-hydroxybenzylcyanide + H2O
4-hydroxyphenylacetic acid + NH3
-
Substrates: at 29% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
4-hydroxycinnamonitrile + H2O
4-hydroxycinnamic acid + NH3
-
Substrates: 431% activity compared to phenylacetonitrile
Products: -
Products: -
?
4-hydroxyphenyl acetonitrile + H2O
4-hydroxybenzoic acid + NH3
-
Substrates: 435% of the activity with mandelonitrile
Products: -
Products: -
ir
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetate + NH3
-
Substrates: best substrate
Products: -
Products: -
?
4-methoxybenzylcyanide + H2O
4-methoxyphenylacetic acid + NH3
-
Substrates: at 62% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
4-methoxyphenylacetonitrile + 2 H2O
4-methoxyphenylacetic acid + NH3
-
Substrates: -
Products: -
Products: -
?
4-methoxyphenylacetonitrile + H2O
4-methoxyphenylacetate + NH3
-
Substrates: 81% of the activity with 4-hydroxyphenylacetonitrile
Products: -
Products: -
?
4-phenylbutyronitrile + H2O
4-phenylbutyrate + NH3
-
Substrates: 86% activity compared to phenylacetonitrile
Products: -
Products: -
?
acrylonitrile + H2O
? + NH3
Substrates: 5% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
adiponitrile + H2O
? + NH3
Substrates: 3% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
adiponitrile + H2O
adipic acid + NH3
-
Substrates: 17.2% of the activity with mandelonitrile
Products: -
Products: -
ir
allyl cyanide + NH3
3-butenoic acid + NH3
-
Substrates: 11% activity compared to phenylacetonitrile
Products: -
Products: -
?
allylcyanide + H2O
? + NH3
Substrates: 12% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
Arylacetonitrile + H2O
?
-
Substrates: pathway in nitrile catabolism, inducible enzyme
Products: -
Products: -
?
benzonitrile + H2O
benzoic acid + NH3
-
Substrates: 1% activity compared to phenylacetonitrile
Products: -
Products: -
?
cinnamonitrile + H2O
cinnamic acid + NH3
-
Substrates: 0.07% activity compared to phenylacetonitrile
Products: -
Products: -
?
crotononitrile + 2 H2O
crotonic acid + NH3
-
Substrates: 4% activity compared to phenylacetonitrile
Products: -
Products: -
?
cyanophenyl acetonitrile + H2O
?
Substrates: -
Products: -
Products: -
?
cyclohexane carbonitrile + H2O
cyclohexlycarboxylic acid + NH3
-
Substrates: 12.5% of the activity with mandelonitrile
Products: -
Products: -
ir
dodecanenitrile + H2O
dodecanoic acid + NH3
-
Substrates: 0.04% activity compared to phenylacetonitrile
Products: -
Products: -
?
fumarodinitrile + 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
Products: -
Products: -
?
glycolonitrile + H2O
glycolic acid + NH3
-
Substrates: 0.08% activity compared to phenylacetonitrile
Products: -
Products: -
?
heptanenitrile + H2O
heptanoic acid + NH3
-
Substrates: 107% activity compared to phenylacetonitrile
Products: -
Products: -
?
hex-5-enenitrile + H2O
hex-5-enoic acid + NH3
-
Substrates: 7.9% of the activity with mandelonitrile
Products: -
Products: -
ir
hexanenitrile + H2O
hexanoic acid + NH3
-
Substrates: 60% activity compared to phenylacetonitrile
Products: -
Products: -
?
hydroxy(2-methoxyphenyl)acetonitrile + H2O
(2R)-hydroxy(2-methoxyphenyl)acetic acid + NH3
-
Substrates: 178% activity compared to phenylacetonitrile
Products: -
Products: -
?
hydroxy(2-methylphenyl)acetonitrile + H2O
(2R)-hydroxy(2-methylphenyl)acetic acid + NH3
-
Substrates: 194% activity compared to phenylacetonitrile
Products: -
Products: -
?
hydroxy(phenyl)acetonitrile + H2O
(2R)-hydroxy(phenyl)acetic acid + NH3
-
Substrates: 404% activity compared to phenylacetonitrile
Products: -
Products: -
?
indole 3-acetonitrile + H2O
(indol-3-yl)acetic acid + NH3
-
Substrates: 319.9% of the activity with mandelonitrile
Products: -
Products: -
ir
isovaleronitrile + H2O
isovaleric acid + NH3
-
Substrates: 11.4% of the activity with mandelonitrile
Products: -
Products: -
ir
m-xylenedicyanide + H2O
?
-
Substrates: at 2.7% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
methylthioacetonitrile + H2O
methylthioacetic acid + NH3
-
Substrates: 72% activity compared to phenylacetonitrile
Products: -
Products: -
?
octanedinitrile + H2O
? + NH3
-
Substrates: 0.14% activity compared to phenylacetonitrile
Products: -
Products: -
?
p-tolylacetonitrile + H2O
p-tolylacetic acid + NH3
-
Substrates: at 72% the rate of 4-chlorobenzylcyanide hydrolysis
Products: -
Products: -
?
phenoxy acetonitrile + H2O
phenoxyacetate + NH3
-
Substrates: 232.6% of the activity with mandelonitrile
Products: -
Products: -
ir
phenyl acetonitrile + H2O
benzoic acid + NH3
-
Substrates: 342.3% of the activity with mandelonitrile
Products: -
Products: -
ir
phenyl glycinenitrile + H2O
phenylalanine + NH3
-
Substrates: 192.5% of the activity with mandelonitrile
Products: -
Products: -
ir
phenyl thioacetonitrile + H2O
thiophenylacetate + NH3
-
Substrates: 187.7% of the activity with mandelonitrile
Products: -
Products: -
ir
rac 2-(methoxy)-mandelonitrile + H2O
(R)-2-(methoxy)-mandelic acid + (S)-2-(methoxy)-mandelic acid + NH3
-
Substrates: -
Products: 10% activity compared to phenylacetonitrile, 92% of the product is the (R)-enantiomer when the overall conversion rate is 50%, at 85% overall conversion, the level of formed (R)-enantiomer is 27%
Products: 10% activity compared to phenylacetonitrile, 92% of the product is the (R)-enantiomer when the overall conversion rate is 50%, at 85% overall conversion, the level of formed (R)-enantiomer is 27%
?
succinonitrile + H2O
succinic acid + NH3
-
Substrates: 0.12% activity compared to phenylacetonitrile
Products: -
Products: -
?
valeronitrile + H2O
? + NH3
Substrates: 25% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
(R,S)-2-phenylpropionitrile + 2 H2O
(S)-2-phenylpropionic acid + NH3
-
Substrates: -
Products: ee 66%
Products: ee 66%
?
(R,S)-2-phenylpropionitrile + 2 H2O
(S)-2-phenylpropionic acid + NH3
-
Substrates: -
Products: ee 66%
Products: ee 66%
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
Substrates: the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion
Products: -
Products: -
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
Substrates: the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion
Products: -
Products: -
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
Substrates: the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion)
Products: -
Products: -
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
Substrates: the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion)
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: the enantiomeric excess against (R)-mandelic acid is over 99%
Products: the enantiomeric excess against (R)-mandelic acid is over 99%
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: the enantiomeric excess against (R)-mandelic acid is over 99%
Products: the enantiomeric excess against (R)-mandelic acid is over 99%
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: ee 22%
Products: ee 22%
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
Substrates: -
Products: ee 22%
Products: ee 22%
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
Substrates: the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
Substrates: the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%. No byproduct is observed
Products: -
Products: -
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
Substrates: the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: -
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: the end product of (R,S)-mandelonitrile transformation at pH 5.0 consists of 40% mandelamide (relative to the total amount of products formed). It is observed that the production of mandelamide is delayed compared to the production of mandelic acid
Products: -
Products: -
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
Substrates: the end product of (R,S)-mandelonitrile transformation at pH 5.0 consists of 40% mandelamide (relative to the total amount of products formed). It is observed that the production of mandelamide is delayed compared to the production of mandelic acid
Products: -
Products: -
?
(R,S)-phenylglycinonitrile + H2O
(S)-phenylglycine + phenylglycine amide + NH3
Substrates: the wild-type enzyme, the previous mainly converts (R,S)-phenylglycinonitrile to (S)-phenylglycine with a low degree of enantioselectivity (ee 42%). In addition, about 8% of phenylglycine amide with a surplus of the (S)-enantiomer (ee 75%) is formed
Products: -
Products: -
?
(R,S)-phenylglycinonitrile + H2O
(S)-phenylglycine + phenylglycine amide + NH3
Substrates: the wild-type enzyme, the previous mainly converts (R,S)-phenylglycinonitrile to (S)-phenylglycine with a low degree of enantioselectivity (ee 42%). In addition, about 8% of phenylglycine amide with a surplus of the (S)-enantiomer (ee 75%) is formed
Products: -
Products: -
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
Substrates: -
Products: the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed
Products: the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
Substrates: -
Products: -
Products: -
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
Substrates: -
Products: the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed
Products: the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: low activity
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: low activity
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: low activity
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
Substrates: 1.87% activity compared to phenylacetonitrile
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
Substrates: activity is 4.2% compared to activity with mandelonitrile
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
Substrates: activity is 4.2% compared to activity with mandelonitrile
Products: -
Products: -
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
Substrates: high activity
Products: -
Products: -
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
Substrates: -
Products: -
Products: -
?
2 (R,S)-2-phenylpropionitrile + 3 H2O
2-phenylpropionic acid + 2-phenylpropionamide + NH3
Substrates: NitP converts (R,S)-2-phenylpropionitrile to 2-phenylpropionic acid with a slight preference for the formation of the S enantiomer, the nitrilase converts only less than 1% of (R,S)-2-phenylpropionitrile to 2-phenylpropionamide
Products: -
Products: -
?
2 (R,S)-2-phenylpropionitrile + 3 H2O
2-phenylpropionic acid + 2-phenylpropionamide + NH3
-
Substrates: deletions of 47 to 67 amino acids (aa) from the carboxy terminus of the nitrilase resulted in variant forms that demonstrated increased amide formation and an increased formation of the (R)-acids
Products: -
Products: -
?
2 (R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + (S)-mandeloamide + NH3
-
Substrates: -
Products: -
Products: -
?
2 (R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + (S)-mandeloamide + NH3
Substrates: NitP shows only weak enantioselectivity for the formation of (R)-mandelic acid from racemic mandelonitrile
Products: the product ratio is about 4:1
Products: the product ratio is about 4:1
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
Substrates: -
Products: -
Products: -
?
2-chloropropionitrile + H2O
? + NH3
Substrates: 86% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
2-chloropropionitrile + H2O
? + NH3
Substrates: 86% compared to the activity with 3-hexenedinitrile
Products: -
Products: -
?
2-cyanophenyl acetonitrile + H2O
?
Substrates: -
Products: -
Products: -
?
2-cyanophenyl acetonitrile + H2O
?
Substrates: -
Products: -
Products: -
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
Substrates: 101% activity compared to phenylacetonitrile
Products: -
Products: -
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
Substrates: activity is 28% compared to activity with mandelonitrile
Products: -
Products: -
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
Substrates: activity is 28% compared to activity with mandelonitrile
Products: -
Products: -
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
Substrates: -
Products: -
Products: -
?
2-hydroxy-2-phenylacetonitrile + 2 H2O