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(2-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(2-bromophenyl)(hydroxy)acetic acid + NH3
-
74% activity compared to phenylacetonitrile
-
-
?
(2-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(2-fluorophenyl)(hydroxy)acetic acid + NH3
-
439% activity compared to phenylacetonitrile
-
-
?
(3-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-bromophenyl)(hydroxy)acetic acid + NH3
-
706% activity compared to phenylacetonitrile
-
-
?
(3-chlorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-chlorophenyl)(hydroxy)acetic acid + NH3
-
810% activity compared to phenylacetonitrile
-
-
?
(3-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(3-fluorophenyl)(hydroxy)acetic acid + NH3
-
454% activity compared to phenylacetonitrile
-
-
?
(4-bromophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-bromophenyl)(hydroxy)acetic acid + NH3
-
680% activity compared to phenylacetonitrile
-
-
?
(4-chlorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-chlorophenyl)(hydroxy)acetic acid + NH3
-
1083% activity compared to phenylacetonitrile
-
-
?
(4-fluorophenyl)(hydroxy)acetonitrile + H2O
(2R)-(4-fluorophenyl)(hydroxy)acetic acid + NH3
-
891% activity compared to phenylacetonitrile
-
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
(S)-2-phenylpropionic acid + NH3
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
(R,S)-mandelonitrile + 2 H2O
(R)-(-)-mandelic acid + NH3
-
-
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)mandelic acid + NH3
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
(R,S)-phenylglycinonitrile + H2O
(S)-phenylglycine + phenylglycine amide + NH3
(S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
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)
-
-
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
1,4-dicyanobutane + H2O
adipic acid + NH3
-
47% activity compared to phenylacetonitrile
-
-
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
1-cyclohexenylacetonitrile + H2O
1-cyclohexenylacetate + NH3
-
at 3.3% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
2 (R,S)-2-phenylpropionitrile + 3 H2O
2-phenylpropionic acid + 2-phenylpropionamide + NH3
2 (R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + (S)-mandeloamide + NH3
2 2-phenylglycinonitrile + 3 H2O
2-phenylglycine + 2-amino-2-phenylacetamide + NH3
-
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
-
-
?
2,4-dichlorobenzylcyanide + H2O
2,4-dichlorophenylacetic acid + NH3
-
at 6.5% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
2-acetyloxy-2-methylphenylacetonitrile + H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
-
-
-
?
2-chlorobenzylcyanide + H2O
2-chlorophenylacetic acid + NH3
-
at 6% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
2-chloromandelonitrile + H2O
(R)-2-chloromandelic acid + NH3
-
33.75% activity compared to phenylacetonitrile
enantioselectivity ee 98.2%
-
?
2-chloromandelonitrile + H2O
2-chloromandelic acid + NH3
-
activity is 20% compared to activity with mandelonitrile
-
-
?
2-chloromandelonitrile + H2O
?
-
-
-
-
?
2-chlorophenyl acetonitrile + H2O
2-chlorobenzoic acid + NH3
-
76.1% of the activity with mandelonitrile
-
-
ir
2-chloropropionitrile + H2O
? + NH3
2-cyanophenyl acetonitrile + H2O
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
2-hydroxy-2-phenylacetonitrile + 2 H2O
2-hydroxy-2-phenylacetate + NH3
2-hydroxy-2-phenylpropionitrile + H2O
2-hydroxy-2-phenylpropionic acid + 2-hydroxy-2-phenylpropionamide + NH3
-
i.e. acetophenone cyanohydrin
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
-
-
-
-
?
2-hydroxy-3-butenenitrile + H2O
? + NH3
2-hydroxybutyronitrile + H2O
? + NH3
2-methoxybenzylcyanide + H2O
2-methoxyphenylacetic acid + NH3
-
at 2% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
2-methoxyphenyl acetonitrile + H2O
2-methoxybenzoic acid + NH3
-
44.5% of the activity with mandelonitrile
-
-
ir
2-methoxyphenylacetonitrile + 2 H2O
2-methoxyphenylacetic acid + NH3
2-methyl-2-phenylpropionitrile + H2O
2-methyl-2-phenylpropionic acid + NH3
-
-
-
-
?
2-methyl-3-butenenitrile + H2O
? + NH3
2-methyleneglutarodinitrile + H2O
? + NH3
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
-
-
?
2-methylglutaronitrile + 4 H2O
2-methylglutaric acid + 2 NH3
-
0.12% activity compared to phenylacetonitrile
-
-
?
2-methylglutaronitrile + H2O
2-methylglutarate + NH3
-
activity is 9.6% compared to activity with mandelonitrile
-
-
?
2-methylglutaronitrile + H2O
? + NH3
-
63% activity compared to phenylacetonitrile
-
-
?
2-phenylbutyronitrile + 2 H2O
2-phenylbutyric acid + NH3
2-phenylbutyronitrile + H2O
2-phenylbutyric acid + NH3
-
0.2% activity compared to phenylacetonitrile
-
-
?
2-phenylglycinonitrile + 2 H2O
2-phenylglycine + NH3
-
3% activity compared to phenylacetonitrile
-
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
2-phenylpropionitrile + H2O
2-phenylpropionate + NH3
-
low activity, 2% activity compared to phenylacetonitrile
-
?
2-phenylpropionitrile + H2O
? + NH3
-
-
-
?
2-phenylvaleronitrile + 2 H2O
2-phenylvaleric acid + NH3
-
-
-
-
?
2-phenylvaleronitrile + H2O
2-phenylvaleric acid + NH3
-
700% of the activity with mandelonitrile
-
-
?
2-thiophene acetonitrile + H2O
thiophene-2-carboxylic acid + NH3
-
137% of the activity with mandelonitrile
-
-
ir
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
2-trimethylsilyloxy-2-phenylacetonitrile + H2O
2-trimethylsilyloxy-2-phenylacetic acid + NH3
-
4% activity compared to phenylacetonitrile
-
-
?
3,4-(methylenedioxy)phenylacetonitrile + H2O
3,4-(methylendioxy)phenylacetic acid + NH3
-
at 65% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
3,4-dichlorobenzylcyanide + H2O
3,4-dichlorophenylacetic acid + NH3
-
at 14% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
3,4-dimethoxyphenylacetonitrile + H2O
?
-
-
-
-
?
3-aminopropionitrile + H2O
3-aminopropanoic acid + NH3
-
7% activity compared to phenylacetonitrile
-
-
?
3-chlorobenzylcyanide + H2O
3-chlorophenylacetic acid + NH3
-
at 43% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
3-cyanopyridine + 2 H2O
nicotinic acid + NH3
3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
-
43.2% activity compared to phenylacetonitrile
-
-
?
3-cyanopyridine + H2O
pyridine 3-carboxylic acid + NH3
3-hexenedinitrile + H2O
? + NH3
-
-
-
?
3-hydroxyglutaronitrile + 4 H2O
3-hydroxyglutaric acid + 2 NH3
-
0.12% activity compared to phenylacetonitrile
-
-
?
3-hydroxyphenylpropionitrile + H2O
3-hydroxyphenylpropionic acid + NH3
3-hydroxypropionitrile + H2O
3-hydroxypropanoate + NH3
-
1% activity compared to phenylacetonitrile
-
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropionic acid + NH3
-
0.07% activity compared to phenylacetonitrile
-
-
?
3-indoleacetonitrile + H2O
3-indoleacetic acid + NH3
3-indolylacetonitrile + H2O
3-indolylacetic acid + NH3
-
2% activity compared to phenylacetonitrile
-
-
?
3-methoxyphenylacetonitrile + 2 H2O
3-methoxyphenylacetic acid + NH3
-
-
-
-
?
3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
3-pyridineacetonitrile + H2O
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
4-aminobenzylcyanide + H2O
4-aminophenylacetic acid + NH3
4-aminophenyl acetonitrile + H2O
4-aminobenzoic acid + NH3
-
502.3% of the activity with mandelonitrile
-
-
ir
4-aminoyphenylacetonitrile + H2O
? + NH3
4-bromobenzylcyanide + H2O
?
4-chlorobenzylcyanide + H2O
4-chlorophenylacetic acid + NH3
4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
4-chlorobutyronitrile + H2O
4-chlorobutyric acid + NH3
-
0.06% activity compared to phenylacetonitrile
-
-
?
4-chlorophenyl acetonitrile + H2O
4-chlorobenzoic acid + NH3
-
360.3% of the activity with mandelonitrile
-
-
ir
4-cyanophenyl acetonitrile + H2O
?
4-cyanopyridine + 2 H2O
4-pyridinecarboxylic acid + NH3
-
512% of the rate with benzonitrile, cell extract
-
-
?
4-cyanopyridine + 2 H2O
pyridine 4-carboxylic acid + NH3
-
142% activity compared to phenylacetonitrile
-
-
?
4-cyanopyridine + H2O
pyridine 4-carboxylic acid + NH3
4-fluorobenzylcyanide + H2O
4-fluorophenylacetic acid + NH3
4-hydroxy benzonitrile + H2O
4-hydroxybenzoate + NH3
-
23.1% of the activity with mandelonitrile
-
-
ir
4-hydroxybenzylcyanide + H2O
4-hydroxyphenylacetic acid + NH3
-
at 29% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
4-hydroxycinnamonitrile + H2O
4-hydroxycinnamic acid + NH3
-
431% activity compared to phenylacetonitrile
-
-
?
4-hydroxyphenyl acetonitrile + H2O
4-hydroxybenzoic acid + NH3
-
435% of the activity with mandelonitrile
-
-
ir
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetate + NH3
-
best substrate
-
-
?
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetic acid + NH3
4-methoxybenzylcyanide + H2O
4-methoxyphenylacetic acid + NH3
-
at 62% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
4-methoxyphenylacetonitrile + 2 H2O
4-methoxyphenylacetic acid + NH3
-
-
-
-
?
4-methoxyphenylacetonitrile + H2O
4-methoxyphenylacetate + NH3
-
81% of the activity with 4-hydroxyphenylacetonitrile
-
-
?
4-nitrobenzylcyanide + H2O
4-nitrophenylacetate + NH3
4-phenylbutyronitrile + H2O
4-phenylbutyrate + NH3
-
86% activity compared to phenylacetonitrile
-
-
?
acrylonitrile + H2O
? + NH3
5% compared to the activity with 3-hexenedinitrile
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
acrylonitrile + H2O
propenoic acid + NH3
adiponitrile + H2O
? + NH3
3% compared to the activity with 3-hexenedinitrile
-
-
?
adiponitrile + H2O
adipic acid + NH3
-
17.2% of the activity with mandelonitrile
-
-
ir
allyl cyanide + NH3
3-butenoic acid + NH3
-
11% activity compared to phenylacetonitrile
-
-
?
allylcyanide + H2O
? + NH3
12% compared to the activity with 3-hexenedinitrile
-
-
?
alpha-methylphenylacetonitrile + H2O
alpha-methylphenylacetic acid + NH3
Arylacetonitrile + H2O
?
-
pathway in nitrile catabolism, inducible enzyme
-
-
?
benzonitrile + 2 H2O
benzoate + NH3
benzonitrile + 2 H2O
benzoic acid + NH3
benzonitrile + H2O
benzoic acid + NH3
-
1% activity compared to phenylacetonitrile
-
-
?
benzylcyanide + H2O
phenylacetic acid + NH3
cinnamonitrile + H2O
cinnamic acid + NH3
-
0.07% activity compared to phenylacetonitrile
-
-
?
crotononitrile + 2 H2O
crotonic acid + NH3
-
4% activity compared to phenylacetonitrile
-
-
?
cyanophenyl acetonitrile + H2O
?
-
-
-
?
cyclohexane carbonitrile + H2O
cyclohexlycarboxylic acid + NH3
-
12.5% of the activity with mandelonitrile
-
-
ir
diphenylacetonitrile + H2O
diphenylacetic acid + NH3
dodecanenitrile + H2O
dodecanoic acid + NH3
-
0.04% activity compared to phenylacetonitrile
-
-
?
fumarodinitrile + H2O
3-cyanoacrylamide + 3-cyanoacrylic acid + NH3
11% compared to the activity with 3-hexenedinitrile. Fumarodinitrile is converted to the monocarboxylate and the monocarboxamide in a ratio of about 65:35
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
glycolonitrile + H2O
glycolic acid + NH3
-
0.08% activity compared to phenylacetonitrile
-
-
?
heptanenitrile + H2O
heptanoic acid + NH3
-
107% activity compared to phenylacetonitrile
-
-
?
hex-5-enenitrile + H2O
hex-5-enoic acid + NH3
-
7.9% of the activity with mandelonitrile
-
-
ir
hexanenitrile + H2O
hexanoic acid + NH3
-
60% activity compared to phenylacetonitrile
-
-
?
hydroxy(2-methoxyphenyl)acetonitrile + H2O
(2R)-hydroxy(2-methoxyphenyl)acetic acid + NH3
-
178% activity compared to phenylacetonitrile
-
-
?
hydroxy(2-methylphenyl)acetonitrile + H2O
(2R)-hydroxy(2-methylphenyl)acetic acid + NH3
-
194% activity compared to phenylacetonitrile
-
-
?
hydroxy(phenyl)acetonitrile + H2O
(2R)-hydroxy(phenyl)acetic acid + NH3
-
404% activity compared to phenylacetonitrile
-
-
?
iminodiacetonitrile + 2 H2O
iminodiacetic acid + 2 NH3
indole 3-acetonitrile + H2O
(indol-3-yl)acetic acid + NH3
-
319.9% of the activity with mandelonitrile
-
-
ir
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
isovaleronitrile + H2O
isovaleric acid + NH3
-
11.4% of the activity with mandelonitrile
-
-
ir
m-tolylacetonitrile + H2O
m-tolylacetic acid + NH3
m-xylenedicyanide + H2O
?
-
at 2.7% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
malononitrile + H2O
malonic acid + NH3
mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
mandelonitrile + 2 H2O
mandelate + NH3
mandelonitrile + 2 H2O
mandelic acid + NH3
mandelonitrile + H2O
mandelic acid + NH3
methylthioacetonitrile + H2O
methylthioacetic acid + NH3
-
72% activity compared to phenylacetonitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid + NH3
o-tolylacetonitrile + H2O
o-tolylacetic acid + NH3
octanedinitrile + H2O
? + NH3
-
0.14% activity compared to phenylacetonitrile
-
-
?
p-tolylacetonitrile + H2O
p-tolylacetic acid + NH3
-
at 72% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
phenoxy acetonitrile + H2O
phenoxyacetate + NH3
-
232.6% of the activity with mandelonitrile
-
-
ir
phenyl acetonitrile + H2O
benzoic acid + NH3
-
342.3% of the activity with mandelonitrile
-
-
ir
phenyl glycinenitrile + H2O
phenylalanine + NH3
-
192.5% of the activity with mandelonitrile
-
-
ir
phenyl thioacetonitrile + H2O
thiophenylacetate + NH3
-
187.7% of the activity with mandelonitrile
-
-
ir
phenylacetonitrile + 2 H2O
phenylacetate + NH3
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
phenylacetonitrile + H2O
?
-
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionate + NH3
phenylpropionitrile + 2 H2O
phenylpropionic acid + NH3
rac 2-(methoxy)-mandelonitrile + H2O
(R)-2-(methoxy)-mandelic acid + (S)-2-(methoxy)-mandelic acid + NH3
-
-
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
-
0.12% activity compared to phenylacetonitrile
-
-
?
valeronitrile + H2O
? + NH3
25% compared to the activity with 3-hexenedinitrile
-
-
?
valeronitrile + H2O
valeric acid + NH3
additional information
?
-
(R,S)-2-phenylpropionitrile + 2 H2O
(S)-2-phenylpropionic acid + NH3
-
-
ee 66%
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
(S)-2-phenylpropionic acid + NH3
-
-
ee 66%
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion
-
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion
-
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion)
-
-
?
(R,S)-2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion)
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)mandelic acid + NH3
-
-
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-(-)mandelic acid + NH3
-
-
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
the enantiomeric excess against (R)-mandelic acid is over 99%
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
-
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
the enantiomeric excess against (R)-mandelic acid is over 99%
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
ee 22%
-
?
(R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
ee 22%
-
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%
-
-
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%. No byproduct is observed
-
-
?
(R,S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
-
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
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
-
-
?
(R,S)-mandelonitrile + 3 H2O
mandelic acid + mandelamide + NH3
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
-
-
?
(R,S)-phenylglycinonitrile + H2O
(S)-phenylglycine + phenylglycine amide + NH3
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
-
-
?
(R,S)-phenylglycinonitrile + H2O
(S)-phenylglycine + phenylglycine amide + NH3
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
-
-
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
-
-
-
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
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
-
-
-
-
?
(S)-mandelonitrile + 2 H2O
(S)-mandelic acid + NH3
-
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
low activity
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
low activity
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
low activity
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
1.87% activity compared to phenylacetonitrile
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
activity is 4.2% compared to activity with mandelonitrile
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
activity is 4.2% compared to activity with mandelonitrile
-
-
?
1,2-phenylenediacetonitrile + H2O
1,2-phenylenediacetic acid + NH3
-
-
-
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
-
-
-
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
-
-
-
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
high activity
-
-
?
1,3-phenylenediacetonitrile + H2O
1,3-phenylenediacetic acid + NH3
-
-
-
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
-
-
-
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
-
-
-
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
-
-
-
?
1,4-phenylenediacetonitrile + H2O
1,4-phenylenediacetic acid + NH3
-
-
-
?
2 (R,S)-2-phenylpropionitrile + 3 H2O
2-phenylpropionic acid + 2-phenylpropionamide + NH3
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
-
-
?
2 (R,S)-2-phenylpropionitrile + 3 H2O
2-phenylpropionic acid + 2-phenylpropionamide + NH3
-
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
-
-
?
2 (R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + (S)-mandeloamide + NH3
-
-
-
-
?
2 (R,S)-mandelonitrile + 2 H2O
(R)-mandelic acid + (S)-mandeloamide + NH3
NitP shows only weak enantioselectivity for the formation of (R)-mandelic acid from racemic mandelonitrile
the product ratio is about 4:1
-
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
-
-
-
?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
2-acetyloxy-2-methylphenylacetic acid + NH3
-
-
-
-
?
2-chloropropionitrile + H2O
? + NH3
86% compared to the activity with 3-hexenedinitrile
-
-
?
2-chloropropionitrile + H2O
? + NH3
86% compared to the activity with 3-hexenedinitrile
-
-
?
2-cyanophenyl acetonitrile + H2O
?
-
-
-
?
2-cyanophenyl acetonitrile + H2O
?
-
-
-
?
2-cyanophenyl acetonitrile + H2O
?
-
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
101% activity compared to phenylacetonitrile
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
activity is 28% compared to activity with mandelonitrile
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
activity is 28% compared to activity with mandelonitrile
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
-
-
-
?
2-hydroxy-2-phenylacetonitrile + 2 H2O
2-hydroxy-2-phenylacetate + NH3
i.e. (R,S)-mandelonitrile
-
-
?
2-hydroxy-2-phenylacetonitrile + 2 H2O
2-hydroxy-2-phenylacetate + NH3
i.e. (R,S)-mandelonitrile
-
-
?
2-hydroxy-2-phenylacetonitrile + 2 H2O
2-hydroxy-2-phenylacetate + NH3
-
i.e. (R,S)-mandelonitrile
-
-
?
2-hydroxy-2-phenylacetonitrile + 2 H2O
2-hydroxy-2-phenylacetate + NH3
-
i.e. (R,S)-mandelonitrile
-
-
?
2-hydroxy-3-butenenitrile + H2O
? + NH3
8% compared to the activity with 3-hexenedinitrile
-
-
?
2-hydroxy-3-butenenitrile + H2O
? + NH3
8% compared to the activity with 3-hexenedinitrile
-
-
?
2-hydroxybutyronitrile + H2O
? + NH3
3% compared to the activity with 3-hexenedinitrile
-
-
?
2-hydroxybutyronitrile + H2O
? + NH3
3% compared to the activity with 3-hexenedinitrile
-
-
?
2-methoxyphenylacetonitrile + 2 H2O
2-methoxyphenylacetic acid + NH3
-
-
-
-
?
2-methoxyphenylacetonitrile + 2 H2O
2-methoxyphenylacetic acid + NH3
-
-
-
-
?
2-methyl-3-butenenitrile + H2O
? + NH3
3% compared to the activity with 3-hexenedinitrile
-
-
?
2-methyl-3-butenenitrile + H2O
? + NH3
3% compared to the activity with 3-hexenedinitrile
-
-
?
2-phenylbutyronitrile + 2 H2O
2-phenylbutyric acid + NH3
-
-
-
-
?
2-phenylbutyronitrile + 2 H2O
2-phenylbutyric acid + NH3
-
-
-
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
-
-
-
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
-
-
12.5% of the activity with mandelonitrile. 65% enantiomeric excess for S-configuration in acid formation, 0.25% of product is amide with 6% enantiomeric excess for R-configuration
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
-
-
(R)-2-phenylpropionic acid is preferentially formed
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
-
-
-
-
?
2-phenylpropionitrile + 2 H2O
2-phenylpropionic acid + NH3
-
-
(R)-2-phenylpropionic acid is preferentially formed
-
?
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
-
-
-
-
?
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
-
ir, at 90% the rate of 4-chlorobenzylcyanide hydrolysis
not via thiopheneacetamide
?
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
-
-
-
-
?
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
-
625% of the activity with mandelonitrile, 1.5% of product is amide
-
-
?
2-thiopheneacetonitrile + H2O
2-thiopheneacetic acid + NH3
-
625% of the activity with mandelonitrile, 1.5% of product is amide
-
-
?
3-cyanopyridine + 2 H2O
nicotinic acid + NH3
-
208% of the rate with benzonitrile, cell extract
-
-
?
3-cyanopyridine + 2 H2O
nicotinic acid + NH3
-
208% of the rate with benzonitrile, cell extract
-
-
?
3-cyanopyridine + H2O
pyridine 3-carboxylic acid + NH3
-
activity is 29% compared to activity with mandelonitrile
-
-
?
3-cyanopyridine + H2O
pyridine 3-carboxylic acid + NH3
-
-
-
?
3-hydroxyphenylpropionitrile + H2O
3-hydroxyphenylpropionic acid + NH3
-
0.12% activity compared to phenylacetonitrile
-
-
?
3-hydroxyphenylpropionitrile + H2O
3-hydroxyphenylpropionic acid + NH3
-
activity is 49% compared to activity with mandelonitrile
-
-
?
3-indoleacetonitrile + H2O
3-indoleacetic acid + NH3
-
-
-
?
3-indoleacetonitrile + H2O
3-indoleacetic acid + NH3
-
at 9% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
3-indoleacetonitrile + H2O
3-indoleacetic acid + NH3
-
-
-
?
3-indoleacetonitrile + H2O
3-indoleacetic acid + NH3
-
at 9% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
-
-
-
-
?
3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
-
at 26% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
3-pyridineacetonitrile + H2O
?
-
-
-
-
?
3-pyridineacetonitrile + H2O
?
-
at 77% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
-
-
-
-
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
-
at 24% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
-
-
-
-
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
-
107% of the activity with mandelonitrile, 1.5% of product is amide
-
-
?
3-thiopheneacetonitrile + H2O
3-thiopheneacetic acid + NH3
-
107% of the activity with mandelonitrile, 1.5% of product is amide
-
-
?
4-aminobenzylcyanide + H2O
4-aminophenylacetic acid + NH3
-
-
-
-
?
4-aminobenzylcyanide + H2O
4-aminophenylacetic acid + NH3
-
at 44% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
4-aminobenzylcyanide + H2O
4-aminophenylacetic acid + NH3
-
high activity
-
-
?
4-aminobenzylcyanide + H2O
4-aminophenylacetic acid + NH3
-
high activity
-
-
?
4-aminoyphenylacetonitrile + H2O
? + NH3
-
-
-
-
?
4-aminoyphenylacetonitrile + H2O
? + NH3
-
-
-
-
?
4-bromobenzylcyanide + H2O
?
-
at 26% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
4-bromobenzylcyanide + H2O
?
-
at 26% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
4-chlorobenzylcyanide + H2O
4-chlorophenylacetic acid + NH3
-
-
-
-
?
4-chlorobenzylcyanide + H2O
4-chlorophenylacetic acid + NH3
-
i.e. p-chlorophenylacetonitrile, best substrate
-
?
4-chlorobenzylcyanide + H2O
4-chlorophenylacetic acid + NH3
-
-
-
-
?
4-chlorobenzylcyanide + H2O
4-chlorophenylacetic acid + NH3
-
i.e. p-chlorophenylacetonitrile, best substrate
-
?
4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
-
59% activity compared to phenylacetonitrile
-
-
?
4-chlorobutyronitrile + H2O
4-chlorobutyrate + NH3
-
59% activity compared to phenylacetonitrile
-
-
?
4-cyanophenyl acetonitrile + H2O
?
-
-
-
?
4-cyanophenyl acetonitrile + H2O
?
-
-
-
?
4-cyanophenyl acetonitrile + H2O
?
high activity
-
-
?
4-cyanopyridine + H2O
pyridine 4-carboxylic acid + NH3
low activity
-
-
?
4-cyanopyridine + H2O
pyridine 4-carboxylic acid + NH3
low activity
-
-
?
4-cyanopyridine + H2O
pyridine 4-carboxylic acid + NH3
-
-
-
?
4-fluorobenzylcyanide + H2O
4-fluorophenylacetic acid + NH3
-
-
-
-
?
4-fluorobenzylcyanide + H2O
4-fluorophenylacetic acid + NH3
-
i.e. p-fluorophenylacetonitrile, at 96% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
4-fluorobenzylcyanide + H2O
4-fluorophenylacetic acid + NH3
-
-
-
-
?
4-fluorobenzylcyanide + H2O
4-fluorophenylacetic acid + NH3
-
i.e. p-fluorophenylacetonitrile, at 96% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetic acid + NH3
-
-
-
-
?
4-hydroxyphenylacetonitrile + H2O
4-hydroxyphenylacetic acid + NH3
-
-
-
-
?
4-nitrobenzylcyanide + H2O
4-nitrophenylacetate + NH3
-
-
-
-
?
4-nitrobenzylcyanide + H2O
4-nitrophenylacetate + NH3
-
at 45% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
-
121% of the rate with benzonitrile, cell extract
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
-
121% of the rate with benzonitrile, cell extract
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
-
0.05% activity compared to phenylacetonitrile
-
-
?
acrylonitrile + H2O
acrylic acid + NH3
-
0.05% activity compared to phenylacetonitrile
-
-
?
acrylonitrile + H2O
propenoic acid + NH3
-
-
-
-
?
acrylonitrile + H2O
propenoic acid + NH3
-
at 7% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
alpha-methylphenylacetonitrile + H2O
alpha-methylphenylacetic acid + NH3
-
0.14% activity compared to phenylacetonitrile
-
-
?
alpha-methylphenylacetonitrile + H2O
alpha-methylphenylacetic acid + NH3
-
activity is 88% compared to activity with mandelonitrile
-
-
?
benzonitrile + 2 H2O
benzoate + NH3
-
activity is 64% compared to activity with mandelonitrile
-
-
?
benzonitrile + 2 H2O
benzoate + NH3
-
activity is 64% compared to activity with mandelonitrile
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
low activity
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
low activity
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
-
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
-
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
21% activity compared to phenylacetonitrile
-
-
?
benzonitrile + 2 H2O
benzoic acid + NH3
-
-
-
?
benzylcyanide + H2O
phenylacetic acid + NH3
-
-
-
-
?
benzylcyanide + H2O
phenylacetic acid + NH3
-
at 53% the rate of 4-chlorobenzylcyanide hydrolysis
-
?
diphenylacetonitrile + H2O
diphenylacetic acid + NH3
-
-
-
?
diphenylacetonitrile + H2O
diphenylacetic acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
0.72% activity compared to phenylacetonitrile
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
0.72% activity compared to phenylacetonitrile
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
fumaronitrile + H2O
fumaric acid + NH3
-
-
-
?
iminodiacetonitrile + 2 H2O
iminodiacetic acid + 2 NH3
-
0.05% activity compared to phenylacetonitrile
-
-
?
iminodiacetonitrile + 2 H2O
iminodiacetic acid + 2 NH3
-
0.05% activity compared to phenylacetonitrile
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
-
35% activity compared to phenylacetonitrile
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
-
22% of the activity with mandelonitrile, 0.1% of product is amide
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
-
-
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
-
-
-
-
?
m-tolylacetonitrile + H2O
m-tolylacetic acid + NH3
-
-
-
-
?
m-tolylacetonitrile + H2O
m-tolylacetic acid + NH3
-
at 32% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
malononitrile + H2O
malonic acid + NH3
-
3.7% activity compared to phenylacetonitrile
-
-
?
malononitrile + H2O
malonic acid + NH3
-
3.7% activity compared to phenylacetonitrile
-
-
?
mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
-
-
99.9% enantiomeric excess for (R)-isomer
-
ir
mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
racemic, enzyme hydrolizes the cyanide functionality to the corresponding carboxylic acid under ambient conditions
-
-
?
mandelonitrile + 2 H2O
(R)-mandelic acid + NH3
racemic, enzyme hydrolizes the cyanide functionality to the corresponding carboxylic acid under ambient conditions
-
-
?
mandelonitrile + 2 H2O
mandelate + NH3
-
-
-
-
?
mandelonitrile + 2 H2O
mandelate + NH3
-
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
at 8% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
4% activity compared to phenylacetonitrile
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
4% activity compared to phenylacetonitrile
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
best substrate, 164% activity compared to phenylacetonitrile
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
best substrate, 164% activity compared to phenylacetonitrile
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
slight preference for the formation of (R)-mandelic acid
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
31% enantiomeric excess for R-configuration in acid formation, 19% of product is amide with 85% enantiomeric excess for S-configuration
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
31% enantiomeric excess for R-configuration in acid formation, 19% of product is amide with 85% enantiomeric excess for S-configuration
-
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
slight preference for the formation of (R)-mandelic acid
-
?
mandelonitrile + 2 H2O
mandelic acid + NH3
-
-
-
?
mandelonitrile + H2O
mandelic acid + NH3
-
-
-
-
?
mandelonitrile + H2O
mandelic acid + NH3
-
-
-
-
?
n-butyronitrile + H2O
n-butyric acid + NH3
-
15% activity compared to phenylacetonitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid + NH3
-
15% activity compared to phenylacetonitrile
-
-
?
o-tolylacetonitrile + H2O
o-tolylacetic acid + NH3
-
-
-
-
?
o-tolylacetonitrile + H2O
o-tolylacetic acid + NH3
-
at 4% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
preferred substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
preferred substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
22% of the rate with benzonitrile, cell extract
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
22% of the rate with benzonitrile, cell extract
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
preferred substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
preferred substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
best substrate
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
activity is 404% compared to activity with mandelonitrile
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
activity is 404% compared to activity with mandelonitrile
-
-
?
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
-
ir
phenylacetonitrile + 2 H2O
phenylacetate + NH3
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
-
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
best substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
best substrate
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
100% activity
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
100% activity
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
206% of the activity with mandelonitrile, 3.9% of product is amide
-
-
?
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
-
206% of the activity with mandelonitrile, 3.9% of product is amide
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionate + NH3
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionate + NH3
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionate + NH3
-
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionate + NH3
-
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionic acid + NH3
-
-
-
-
?
phenylpropionitrile + 2 H2O
phenylpropionic acid + NH3
-
-
-
-
?
valeronitrile + H2O
valeric acid + NH3
-
57% activity compared to phenylacetonitrile
-
-
?
valeronitrile + H2O
valeric acid + NH3
-
0.08% activity compared to phenylacetonitrile
-
-
?
valeronitrile + H2O
valeric acid + NH3
-
12.5% of the activity with mandelonitrile
-
-
?
additional information
?
-
-
very poor substrates (less than 1.5% the rate of 4-chlorobenzylcyanide hydrolysis) are 1,4-dichlorobenzylcyanide, 4-nitrobenzylcyanide, 2-pyridineacetonitrile, 2-phenylpropionitrile, 1-naphthylacetonitrile, diphenylacetonitrile, o-xylenedicyanide, acetonitrile (i.e. methylcyanide). No substrates are 2,6-dichlorobenzylcyanide, allylcyanide, propionitrile, aminoacetonitrile, iminodiacetonitrile, methacrylonitrile, crotonitrile, benzonitrile, 2- or 3-cyanopyridine, cyanopyrazine, 2-thiophenecarbonitrile or 2-furaneacrylonitrile
-
-
?
additional information
?
-
-
though the enzyme exhibits activity toward both classes of aromatic and arylacetonitriles, the nitrilase shows higher activity toward the arylacetonitriles, substrate specificity and substrate docking study, overview. No activity toward aminobutytonitrile, 2,2-dimethylcyclopropyl cyanide, and 2-amino-2,3-dimethylbutanenitrile, very low activity toward 4-aminobenzonitrile and iminodiacetonitrile, overview
-
-
?
additional information
?
-
-
very poor substrates (less than 1.5% the rate of 4-chlorobenzylcyanide hydrolysis) are 1,4-dichlorobenzylcyanide, 4-nitrobenzylcyanide, 2-pyridineacetonitrile, 2-phenylpropionitrile, 1-naphthylacetonitrile, diphenylacetonitrile, o-xylenedicyanide, acetonitrile (i.e. methylcyanide). No substrates are 2,6-dichlorobenzylcyanide, allylcyanide, propionitrile, aminoacetonitrile, iminodiacetonitrile, methacrylonitrile, crotonitrile, benzonitrile, 2- or 3-cyanopyridine, cyanopyrazine, 2-thiophenecarbonitrile or 2-furaneacrylonitrile
-
-
?
additional information
?
-
-
though the enzyme exhibits activity toward both classes of aromatic and arylacetonitriles, the nitrilase shows higher activity toward the arylacetonitriles, substrate specificity and substrate docking study, overview. No activity toward aminobutytonitrile, 2,2-dimethylcyclopropyl cyanide, and 2-amino-2,3-dimethylbutanenitrile, very low activity toward 4-aminobenzonitrile and iminodiacetonitrile, overview
-
-
?
additional information
?
-
the purified enzyme has very little activity against heterocyclic and aliphatic nitriles like 2-cyanopyridine and 4-cyanopyridine, and no activity is recorded against aromatic nitriles like benzonitrile, 4-hydroxynitrile, and tolunitrile
-
-
?
additional information
?
-
the purified enzyme has very little activity against heterocyclic and aliphatic nitriles like 2-cyanopyridine and 4-cyanopyridine, and no activity is recorded against aromatic nitriles like benzonitrile, 4-hydroxynitrile, and tolunitrile
-
-
?
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine
-
-
-
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine
-
-
-
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine
-
-
-
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine
-
-
-
additional information
?
-
-
does not use 2-(N,N-dimethylamino)-2-phenylacetonitrile, 2-phenylpropionitrile, and 2-phenylbutyronitrile as substrate
-
-
?
additional information
?
-
-
does not use 2-(N,N-dimethylamino)-2-phenylacetonitrile, 2-phenylpropionitrile, and 2-phenylbutyronitrile as substrate
-
-
?
additional information
?
-
-
enzyme converts the isomers carrying a substituent in the meta-position with higher relative activities than the corresponding para- or ortho-substituted isomers. Aliphatic substrates such as acrylonitrile and 2-hydroxy-3-butenenitrile are also hydrolysed
-
-
?
additional information
?
-
-
enzyme converts the isomers carrying a substituent in the meta-position with higher relative activities than the corresponding para- or ortho-substituted isomers. Aliphatic substrates such as acrylonitrile and 2-hydroxy-3-butenenitrile are also hydrolysed
-
-
?
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine
-
-
-
additional information
?
-
very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine
-
-
-
additional information
?
-
-
no activity with benzonitrile, 2-cyanotoluene, 3-cyanotoluene, 3-cyanobenzothiophene, propionitrile, butyronitrile, and valeronitrile, 2-phenylbutyronitrile is a poor substrate, enzyme is enantioselective and specific for arylacetonitriles
-
?
additional information
?
-
-
enzyme acts as nitrilase and hydratase. relative amounts of amides formed from different nitriles increase with an increasing negative inductive effect of the substituent in 2-position. Acids and amides formed from chiral nitriles demonstrate mostly opposite enantiomeric excess
-
-
?
additional information
?
-
-
the nitrilase from strain EBC191 hydrolyzes a wide range of arylacetonitriles, such as 2-phenylpropionitrile (2-methylphenylacetonitrile), 2-phenylbutyronitrile, or 2-phenylvaleronitrile, and also alpha-hydroxynitriles, such as mandelonitrile, with rather high specific activities. The enzyme catalyzes the reactions of nitrilase, EC 3.5.5.1, and arylacetonitrilase, EC 3.5.5.5, substrate specificity and enantioselectivity, overview. Steric hindrance with amino acid residue Tyr54 impairs the binding or conversion of sterically demanding substrates, homology modelling
-
-
?
additional information
?
-
the enzyme shows preference for unsaturated aliphatic substrates containing 5-6 carbon atoms. Increased reaction rates are also found for aliphatic nitriles carrying electron withdrawing substituents (e.g. chloro- or hydroxy-groups) close to the nitrile group. Aliphatic dinitriles are attacked only at one of the nitrile groups and with most of the tested dinitriles the monocarboxylates are detected as major products. Substrates converted with 1% less compared to the activity with 3-hexenedinitrile: 2-methylbutyronitrile, decanedinitrile, octanedinitrile, cis,trans-crotononitrile, popionitrile, isovaleronitrile, lactonitrile, butyronitrile,
-
-
-
additional information
?
-
-
the nitrilase from strain EBC191 hydrolyzes a wide range of arylacetonitriles, such as 2-phenylpropionitrile (2-methylphenylacetonitrile), 2-phenylbutyronitrile, or 2-phenylvaleronitrile, and also alpha-hydroxynitriles, such as mandelonitrile, with rather high specific activities. The enzyme catalyzes the reactions of nitrilase, EC 3.5.5.1, and arylacetonitrilase, EC 3.5.5.5, substrate specificity and enantioselectivity, overview. Steric hindrance with amino acid residue Tyr54 impairs the binding or conversion of sterically demanding substrates, homology modelling
-
-
?
additional information
?
-
-
enzyme acts as nitrilase and hydratase. relative amounts of amides formed from different nitriles increase with an increasing negative inductive effect of the substituent in 2-position. Acids and amides formed from chiral nitriles demonstrate mostly opposite enantiomeric excess
-
-
?
additional information
?
-
the enzyme shows preference for unsaturated aliphatic substrates containing 5-6 carbon atoms. Increased reaction rates are also found for aliphatic nitriles carrying electron withdrawing substituents (e.g. chloro- or hydroxy-groups) close to the nitrile group. Aliphatic dinitriles are attacked only at one of the nitrile groups and with most of the tested dinitriles the monocarboxylates are detected as major products. Substrates converted with 1% less compared to the activity with 3-hexenedinitrile: 2-methylbutyronitrile, decanedinitrile, octanedinitrile, cis,trans-crotononitrile, popionitrile, isovaleronitrile, lactonitrile, butyronitrile,
-
-
-
additional information
?
-
-
the enzyme shows preference for unsaturated aliphatic substrates containing 5-6 carbon atoms. Increased reaction rates are also found for aliphatic nitriles carrying electron withdrawing substituents (e.g. chloro- or hydroxy-groups) close to the nitrile group. Aliphatic dinitriles are attacked only at one of the nitrile groups and with most of the tested dinitriles the monocarboxylates are detected as major products. Substrates converted with 1% less compared to the activity with 3-hexenedinitrile: 2-methylbutyronitrile, decanedinitrile, octanedinitrile, cis,trans-crotononitrile, popionitrile, isovaleronitrile, lactonitrile, butyronitrile,
-
-
-
additional information
?
-
-
activity of less than 1% compared to the activity with madelonitrile: fumaronitrile, 3-hydroxyglutaronitrile, succinonitrile, 3-hydroxypropionitrile. The enzyme hydrolyzes nitriles with diverse structures. Arylacetonitriles are the optimal substrates
-
-
-
additional information
?
-
-
activity of less than 1% compared to the activity with madelonitrile: fumaronitrile, 3-hydroxyglutaronitrile, succinonitrile, 3-hydroxypropionitrile. The enzyme hydrolyzes nitriles with diverse structures. Arylacetonitriles are the optimal substrates
-
-
-
additional information
?
-
-
enzyme requires an oxygen atom in para-position of the substrate. Indole-3-acetonitrile, arylcyanides, and arylpropionitriles are poor substrates
-
-
?
additional information
?
-
very low activity with: (R,S)-Mandelonitrile
-
-
-
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-
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5
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Nitrilase from Pseudomonas fluorescens EBC191: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme
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80
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20
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brenda
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enantioselective nitrilase from Pseudomonas putida: cloning, heterologous expression, and bioreactor studies
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41
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Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes
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Sinapis alba
brenda
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Characterisation of the substrate specificity of the nitrile hydrolyzing system of the acidotolerant black yeast Exophiala oligosperma R1
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61
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brenda
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Identification of amino acid residues responsible for the enantioselectivity and amide formation capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191
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75
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Pseudomonas fluorescens (Q5EG61), Pseudomonas fluorescens
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Construction and application of variants of the Pseudomonas fluorescens EBC191 arylacetonitrilase for increased production of acids or amides
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76
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Microbial nitrilases: Versatile, spiral forming, industrial enzymes
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106
703-727
2009
Alcaligenes faecalis, Alcaligenes faecalis ATCC 8750
brenda
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Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401
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37
741-750
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brenda
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Pseudomonas syringae pv. syringae B728a hydrolyses indole-3-acetonitrile to the plant hormone indole-3-acetic acid
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10
857-865
2009
Pseudomonas syringae pv. syringae, no activity in no activity in Pseudomonas syringae pv. tomato, Pseudomonas syringae pv. syringae B728a
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Synthesis of enantiomerically pure (S)-mandelic acid using anoxynitrilasenitrilase bienzymatic cascade: a nitrilase surprisingly shows nitrile hydratase activity
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351
1531 - 1538
2009
Pseudomonas fluorescens (Q5EG61), Pseudomonas fluorescens EBC191 (Q5EG61)
-
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Stabilisation of oxygen-labile nitrilases via co-aggregation with poly(ethyleneimine)
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38
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2006
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-
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Synthesis of enantiomerically pure (S)-mandelic acid using anoxynitrilasenitrilase bienzymatic cascade: a nitrilase surprisingly shows nitrile hydratase activity
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17
320-323
2006
Pseudomonas fluorescens (Q5EG61), Pseudomonas fluorescens EBC191 (Q5EG61)
-
brenda
Baum, S.; Williamson, D.S.; Sewell, T.; Stolz, A.
Conversion of sterically demanding alpha,alpha-disubstituted phenylacetonitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191
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78
48-57
2012
Pseudomonas fluorescens, Pseudomonas fluorescens EBC191
brenda
Petrickova, A.; Vesela, A.B.; Kaplan, O.; Kubac, D.; Uhnakova, B.; Malandra, A.; Felsberg, J.; Rinagelova, A.; Weyrauch, P.; K?en, V.; Bezouska, K.; Martinkova, L.
Purification and characterization of heterologously expressed nitrilases from filamentous fungi
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93
1553-1561
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Neurospora crassa, Aspergillus niger (A2R6M7), Aspergillus niger (A9QXE0), Aspergillus niger CBS 513.88 (A2R6M7), Aspergillus niger CBS 513.88 (A9QXE0), Neurospora crassa OR74A
brenda
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Autodisplay of nitrilase from Alcaligenes faecalis in E. coli yields a whole cell biocatalyst for the synthesis of enantiomerically pure (R)-mandelic Acid
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3
719-725
2011
Alcaligenes faecalis, Alcaligenes faecalis ATCC 8750
-
brenda
Liu, Z.Q.; Dong, L.Z.; Cheng, F.; Xue, Y.P.; Wang, Y.S.; Ding, J.N.; Zheng, Y.G.; Shen, Y.C.
Gene cloning, expression, and characterization of a nitrilase from Alcaligenes faecalis ZJUTB10
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59
11560-11570
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Alcaligenes faecalis, Alcaligenes faecalis ZJUTB10
brenda
Sosedov, O.; Stolz, A.
Improvement of the amides forming capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191 by site-directed mutagenesis
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99
2623-2635
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Pseudomonas fluorescens, Pseudomonas fluorescens EBC191
brenda
Bhatia, S.; Mehta, P.; Bhatia, R.; Bhalla, T.
Purification and characterization of arylacetonitrile-specific nitrilase of Alcaligenes sp. MTCC 10675
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61
459-465
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brenda
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Cloning, purification and evaluation of the enzymatic properties of a novel arylacetonitrilase from Luminiphilus syltensis NOR5-1B: a potential biocatalyst for the synthesis of mandelic acid and its derivatives
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37
1655-1661
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brenda
Petrickova, A.; Sosedov, O.; Baum, S.; Stolz, A.; Martinkova, L.
Influence of point mutations near the active site on the catalytic properties of fungal arylacetonitrilases from Aspergillus niger and Neurospora crassa
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77
74-80
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-
brenda
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Bringing nitrilase sequences from databases to life the search for novel substrate specificities with a focus on dinitriles
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100
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2016
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103
6737-6746
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brenda
Sun, H.; Wang, H.; Gao, W.; Chen, L.; Wu, K.; Wei, D.
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468
820-825
2015
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brenda
Sun, H.; Gao, W.; Wang, H.; Wei, D.
Expression, characterization of a novel nitrilase PpL19 from Pseudomonas psychrotolerans with S-selectivity toward mandelonitrile present in active inclusion bodies
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38
455-461
2016
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brenda
Vesela, A.; Krenkova, A.; Martinkova, L.
Exploring the potential of fungal arylacetonitrilases in mandelic acid synthesis
Mol. Biotechnol.
57
466-474
2015
Aspergillus niger
-
brenda
Thakur, N.; Kumar, V.; Thakur, S.; Sharma, N.; Sheeta, S.; Bhalla, T.
Biotransformation of 4-hydroxyphenylacetonitrile to 4-hydroxyphenylacetic acid using whole cell arylacetonitrilase of Alcaligenes faecalis MTCC 12629
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73
117-123
2018
Alcaligenes faecalis, Alcaligenes faecalis MTCC 12629
-
brenda
Brunner, S.; Eppinger, E.; Fischer, S.; Groening, J.; Stolz, A.
Conversion of aliphatic nitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191
World J. Microbiol. Biotechnol.
34
91
2018
Pseudomonas fluorescens (Q5EG61), Pseudomonas fluorescens EBC191 (Q5EG61), Pseudomonas fluorescens EBC191
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