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Information on EC 3.5.5.5 - Arylacetonitrilase
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3.5.5.5 ArylacetonitrilaseIUBMB Comments
Requires thiol compounds. Also hydrolyses other 4-substituted phenylacetonitriles, thien-2-ylacetonitrile, tolylacetonitriles, and, more slowly, benzyl cyanide.
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Word Map
- 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
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
arylacetonitrilase, gpnor51, nitmp, nitan, nitrilase ppl19, blr3397, enantioselective arylacetonitrilase, arylacetonitrile-hydrolyzing nitrilase, 
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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-
-
-
-
-
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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
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis
hydrolysis of nitriles
hydrolysis of nitriles
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
Arylacetonitrile aminohydrolase
Requires thiol compounds. Also hydrolyses other 4-substituted phenylacetonitriles, thien-2-ylacetonitrile, tolylacetonitriles, and, more slowly, benzyl cyanide.
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CAS REGISTRY NUMBER
COMMENTARY
132053-06-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
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
-
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
-
-
?
(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)
-
-
?
1,4-dicyanobutane + H2O
adipic acid + NH3
-
47% activity compared to phenylacetonitrile
-
-
?
1-cyclohexenylacetonitrile + H2O
1-cyclohexenylacetate + NH3
-
at 3.3% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
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-chlorophenyl acetonitrile + H2O
2-chlorobenzoic acid + NH3
-
76.1% of the activity with mandelonitrile
-
-
ir
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-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-methyl-2-phenylpropionitrile + H2O
2-methyl-2-phenylpropionic acid + 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 + 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 + H2O
2-phenylpropionate + NH3
-
low activity, 2% activity compared to phenylacetonitrile
-
?
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-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-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
pyridine 3-carboxylic acid + NH3
-
43.2% activity compared to phenylacetonitrile
-
-
?
3-hydroxyglutaronitrile + 4 H2O
3-hydroxyglutaric acid + 2 NH3
-
0.12% activity compared to phenylacetonitrile
-
-
?
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-indolylacetonitrile + H2O
3-indolylacetic acid + NH3
-
2% activity compared to phenylacetonitrile
-
-
?
3-methoxyphenylacetonitrile + 2 H2O
3-methoxyphenylacetic acid + NH3
-
-
-
-
?
4-aminophenyl acetonitrile + H2O
4-aminobenzoic acid + NH3
-
502.3% of the activity with mandelonitrile
-
-
ir
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-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-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-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-phenylbutyronitrile + H2O
4-phenylbutyrate + NH3
-
86% activity compared to phenylacetonitrile
-
-
?
acrylonitrile + H2O
? + NH3
5% compared to the activity with 3-hexenedinitrile
-
-
?
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
-
-
?
Arylacetonitrile + H2O
?
-
pathway in nitrile catabolism, inducible enzyme
-
-
?
benzonitrile + H2O
benzoic acid + NH3
-
1% activity compared to phenylacetonitrile
-
-
?
cinnamonitrile + H2O
cinnamic acid + NH3
-
0.07% activity compared to phenylacetonitrile
-
-
?
crotononitrile + 2 H2O
crotonic acid + NH3
-
4% activity compared to phenylacetonitrile
-
-
?
cyclohexane carbonitrile + H2O
cyclohexlycarboxylic acid + NH3
-
12.5% of the activity with mandelonitrile
-
-
ir
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
-
-
?
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
-
-
?
indole 3-acetonitrile + H2O
(indol-3-yl)acetic acid + NH3
-
319.9% of the activity with mandelonitrile
-
-
ir
isovaleronitrile + H2O
isovaleric acid + NH3
-
11.4% of the activity with mandelonitrile
-
-
ir
m-xylenedicyanide + H2O
?
-
at 2.7% the rate of 4-chlorobenzylcyanide hydrolysis
-
-
?
methylthioacetonitrile + H2O
methylthioacetic acid + NH3
-
72% activity compared to phenylacetonitrile
-
-
?
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
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
-
-
?
(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
-
-
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
(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
-
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
-
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
-
-
-
?