3.5.5.5 (2-bromophenyl)(hydroxy)acetonitrile + H2O 74% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(2-bromophenyl)(hydroxy)acetic acid + NH3 - ? 432989 3.5.5.5 (2-fluorophenyl)(hydroxy)acetonitrile + H2O 439% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(2-fluorophenyl)(hydroxy)acetic acid + NH3 - ? 432992 3.5.5.5 (3-bromophenyl)(hydroxy)acetonitrile + H2O 706% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(3-bromophenyl)(hydroxy)acetic acid + NH3 - ? 432997 3.5.5.5 (3-chlorophenyl)(hydroxy)acetonitrile + H2O 810% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(3-chlorophenyl)(hydroxy)acetic acid + NH3 - ? 432998 3.5.5.5 (3-fluorophenyl)(hydroxy)acetonitrile + H2O 454% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(3-fluorophenyl)(hydroxy)acetic acid + NH3 - ? 432999 3.5.5.5 (4-bromophenyl)(hydroxy)acetonitrile + H2O 680% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(4-bromophenyl)(hydroxy)acetic acid + NH3 - ? 433001 3.5.5.5 (4-chlorophenyl)(hydroxy)acetonitrile + H2O 1083% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(4-chlorophenyl)(hydroxy)acetic acid + NH3 - ? 433002 3.5.5.5 (4-fluorophenyl)(hydroxy)acetonitrile + H2O 891% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-(4-fluorophenyl)(hydroxy)acetic acid + NH3 - ? 433003 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens (S)-2-phenylpropionic acid + NH3 ee 66% ? 433044 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens EBC191 (S)-2-phenylpropionic acid + NH3 ee 66% ? 433044 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion) Neurospora crassa 2-phenylpropionic acid + NH3 - ? 433045 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion Aspergillus niger 2-phenylpropionic acid + NH3 - ? 433045 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O the enzyme exhibits a low degree of enantioselectivity toward this substrate (e.e. 35% for the (R)-acid at 35% conversion) Neurospora crassa DSM 1257 2-phenylpropionic acid + NH3 - ? 433045 3.5.5.5 (R,S)-2-phenylpropionitrile + 2 H2O the enzyme produces (R)-2-phenylpropionic acid with an e.e.-value of 90% at 28% conversion Aspergillus niger CBS 513.88 2-phenylpropionic acid + NH3 - ? 433045 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis (R)-(-)-mandelic acid + NH3 - ? 413756 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis (R)-(-)mandelic acid + NH3 - ? 413757 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis ATCC 8750 (R)-(-)mandelic acid + NH3 - ? 413757 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis (R)-mandelic acid + NH3 - ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis (R)-mandelic acid + NH3 the enantiomeric excess against (R)-mandelic acid is over 99% ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens (R)-mandelic acid + NH3 ee 22% ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens EBC191 (R)-mandelic acid + NH3 ee 22% ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis ATCC 8750 (R)-mandelic acid + NH3 - ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O - Alcaligenes faecalis ZJUTB10 (R)-mandelic acid + NH3 the enantiomeric excess against (R)-mandelic acid is over 99% ? 419698 3.5.5.5 (R,S)-mandelonitrile + 2 H2O the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7% Pseudomonas psychrotolerans (S)-mandelic acid + NH3 - ? 454758 3.5.5.5 (R,S)-mandelonitrile + 2 H2O the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7%. No byproduct is observed Pseudomonas psychrotolerans (S)-mandelic acid + NH3 - ? 454758 3.5.5.5 (R,S)-mandelonitrile + 2 H2O the enzyme hydrolyzes racemic mandelonitrile to (S)-mandelic acid with an enantiomeric excess value of 52.7% Pseudomonas psychrotolerans L19 (S)-mandelic acid + NH3 - ? 454758 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Auricularia delicata mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Aspergillus luchuensis mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Macrophomina phaseolina mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O 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 Neurospora crassa mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess Aspergillus niger mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Macrophomina phaseolina MS6 mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Auricularia delicata TFB-10046 SS5 mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O 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 Neurospora crassa DSM 1257 mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O - Aspergillus luchuensis IFO 4308 mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-mandelonitrile + 3 H2O the enzyme produces almost no mandelamide at pH 5 (Fig. 1a), while the R-acid is formed with a high enantiomeric excess Aspergillus niger CBS 513.88 mandelic acid + mandelamide + NH3 - ? 433047 3.5.5.5 (R,S)-phenylglycinonitrile + H2O 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 Pseudomonas fluorescens (S)-phenylglycine + phenylglycine amide + NH3 - ? 454759 3.5.5.5 (R,S)-phenylglycinonitrile + H2O 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 Pseudomonas fluorescens EBC191 (S)-phenylglycine + phenylglycine amide + NH3 - ? 454759 3.5.5.5 (S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens (S)-mandelic acid + NH3 - ? 395170 3.5.5.5 (S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens (S)-mandelic acid + NH3 the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed ? 395170 3.5.5.5 (S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens EBC191 (S)-mandelic acid + NH3 - ? 395170 3.5.5.5 (S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens EBC191 (S)-mandelic acid + NH3 the product is 94% enantiomeric pure (S)-isomer, the formation of ca 50% (S)-mandeloamide is observed ? 395170 3.5.5.5 (S)-mandelonitrile + 2 H2O 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) Aspergillus niger (R)-mandelic acid + NH3 - ? 454765 3.5.5.5 1,2-phenylenediacetonitrile + H2O - Macrophomina phaseolina 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O - Trichoderma virens Gv29-8 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O low activity Auricularia delicata 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O low activity Aspergillus luchuensis 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O 1.87% activity compared to phenylacetonitrile Luminiphilus syltensis 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O activity is 4.2% compared to activity with mandelonitrile Pseudomonas psychrotolerans 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O - Macrophomina phaseolina MS6 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O low activity Aspergillus luchuensis IFO 4308 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,2-phenylenediacetonitrile + H2O activity is 4.2% compared to activity with mandelonitrile Pseudomonas psychrotolerans L19 1,2-phenylenediacetic acid + NH3 - ? 433070 3.5.5.5 1,3-phenylenediacetonitrile + H2O - Auricularia delicata 1,3-phenylenediacetic acid + NH3 - ? 454781 3.5.5.5 1,3-phenylenediacetonitrile + H2O - Aspergillus luchuensis 1,3-phenylenediacetic acid + NH3 - ? 454781 3.5.5.5 1,3-phenylenediacetonitrile + H2O - Trichoderma virens Gv29-8 1,3-phenylenediacetic acid + NH3 - ? 454781 3.5.5.5 1,3-phenylenediacetonitrile + H2O high activity Macrophomina phaseolina 1,3-phenylenediacetic acid + NH3 - ? 454781 3.5.5.5 1,4-dicyanobutane + H2O 47% activity compared to phenylacetonitrile Bradyrhizobium japonicum adipic acid + NH3 - ? 395198 3.5.5.5 1,4-phenylenediacetonitrile + H2O - Auricularia delicata 1,4-phenylenediacetic acid + NH3 - ? 454782 3.5.5.5 1,4-phenylenediacetonitrile + H2O - Aspergillus luchuensis 1,4-phenylenediacetic acid + NH3 - ? 454782 3.5.5.5 1,4-phenylenediacetonitrile + H2O - Macrophomina phaseolina 1,4-phenylenediacetic acid + NH3 - ? 454782 3.5.5.5 1,4-phenylenediacetonitrile + H2O - Trichoderma virens Gv29-8 1,4-phenylenediacetic acid + NH3 - ? 454782 3.5.5.5 1-cyclohexenylacetonitrile + H2O at 3.3% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 1-cyclohexenylacetate + NH3 - ? 18112 3.5.5.5 2 (R,S)-2-phenylpropionitrile + 3 H2O 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 Pseudomonas fluorescens 2-phenylpropionic acid + 2-phenylpropionamide + NH3 - ? 413754 3.5.5.5 2 (R,S)-2-phenylpropionitrile + 3 H2O 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 Pseudomonas fluorescens 2-phenylpropionic acid + 2-phenylpropionamide + NH3 - ? 413754 3.5.5.5 2 (R,S)-mandelonitrile + 2 H2O - Pseudomonas fluorescens (R)-mandelic acid + (S)-mandeloamide + NH3 - ? 413758 3.5.5.5 2 (R,S)-mandelonitrile + 2 H2O NitP shows only weak enantioselectivity for the formation of (R)-mandelic acid from racemic mandelonitrile Pseudomonas fluorescens (R)-mandelic acid + (S)-mandeloamide + NH3 the product ratio is about 4:1 ? 413758 3.5.5.5 2 2-phenylglycinonitrile + 3 H2O 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 Pseudomonas fluorescens 2-phenylglycine + 2-amino-2-phenylacetamide + NH3 - ? 383783 3.5.5.5 2,4-dichlorobenzylcyanide + H2O at 6.5% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 2,4-dichlorophenylacetic acid + NH3 - ? 18105 3.5.5.5 2-acetyloxy-2-methylphenylacetonitrile + 2 H2O - Pseudomonas fluorescens 2-acetyloxy-2-methylphenylacetic acid + NH3 - ? 419247 3.5.5.5 2-acetyloxy-2-methylphenylacetonitrile + 2 H2O - Pseudomonas fluorescens EBC191 2-acetyloxy-2-methylphenylacetic acid + NH3 - ? 419247 3.5.5.5 2-acetyloxy-2-methylphenylacetonitrile + H2O - Pseudomonas fluorescens 2-acetyloxy-2-methylphenylacetic acid + NH3 - ? 433163 3.5.5.5 2-chlorobenzylcyanide + H2O at 6% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 2-chlorophenylacetic acid + NH3 - ? 18098 3.5.5.5 2-chloromandelonitrile + H2O - Alcaligenes faecalis ? - ? 413187 3.5.5.5 2-chloromandelonitrile + H2O 33.75% activity compared to phenylacetonitrile Luminiphilus syltensis (R)-2-chloromandelic acid + NH3 enantioselectivity ee 98.2% ? 433190 3.5.5.5 2-chloromandelonitrile + H2O activity is 20% compared to activity with mandelonitrile Pseudomonas psychrotolerans 2-chloromandelic acid + NH3 - ? 454914 3.5.5.5 2-chlorophenyl acetonitrile + H2O 76.1% of the activity with mandelonitrile Pseudomonas putida 2-chlorobenzoic acid + NH3 - ir 383749 3.5.5.5 2-chloropropionitrile + H2O 86% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 454918 3.5.5.5 2-chloropropionitrile + H2O 86% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens EBC191 ? + NH3 - ? 454918 3.5.5.5 2-cyanophenyl acetonitrile + H2O - Auricularia delicata ? - ? 454919 3.5.5.5 2-cyanophenyl acetonitrile + H2O - Aspergillus luchuensis ? - ? 454919 3.5.5.5 2-cyanophenyl acetonitrile + H2O - Macrophomina phaseolina ? - ? 454919 3.5.5.5 2-cyanopyridine + 2 H2O - Trichoderma virens Gv29-8 pyridine 2-carboxylic acid + NH3 - ? 371654 3.5.5.5 2-cyanopyridine + 2 H2O 101% activity compared to phenylacetonitrile Luminiphilus syltensis pyridine 2-carboxylic acid + NH3 - ? 371654 3.5.5.5 2-cyanopyridine + 2 H2O activity is 28% compared to activity with mandelonitrile Pseudomonas psychrotolerans pyridine 2-carboxylic acid + NH3 - ? 371654 3.5.5.5 2-cyanopyridine + 2 H2O activity is 28% compared to activity with mandelonitrile Pseudomonas psychrotolerans L19 pyridine 2-carboxylic acid + NH3 - ? 371654 3.5.5.5 2-hydroxy-2-phenylacetonitrile + 2 H2O i.e. (R,S)-mandelonitrile Neurospora crassa 2-hydroxy-2-phenylacetate + NH3 - ? 419899 3.5.5.5 2-hydroxy-2-phenylacetonitrile + 2 H2O i.e. (R,S)-mandelonitrile Aspergillus niger 2-hydroxy-2-phenylacetate + NH3 - ? 419899 3.5.5.5 2-hydroxy-2-phenylacetonitrile + 2 H2O i.e. (R,S)-mandelonitrile Aspergillus niger CBS 513.88 2-hydroxy-2-phenylacetate + NH3 - ? 419899 3.5.5.5 2-hydroxy-2-phenylacetonitrile + 2 H2O i.e. (R,S)-mandelonitrile Neurospora crassa OR74A 2-hydroxy-2-phenylacetate + NH3 - ? 419899 3.5.5.5 2-hydroxy-2-phenylpropionitrile + H2O i.e. acetophenone cyanohydrin Pseudomonas fluorescens 2-hydroxy-2-phenylpropionic acid + 2-hydroxy-2-phenylpropionamide + NH3 product ratio of about 3.4:1 for 2-hydroxy-2-phenylpropionic acid and 2-hydroxy-2-phenylpropionamide ? 433197 3.5.5.5 2-hydroxy-3-butenenitrile + H2O - Exophiala oligosperma 2-hydroxy-3-butenoic acid + NH3 - ? 403548 3.5.5.5 2-hydroxy-3-butenenitrile + H2O 8% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 454927 3.5.5.5 2-hydroxy-3-butenenitrile + H2O 8% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens EBC191 ? + NH3 - ? 454927 3.5.5.5 2-hydroxybutyronitrile + H2O 3% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 454930 3.5.5.5 2-hydroxybutyronitrile + H2O 3% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens EBC191 ? + NH3 - ? 454930 3.5.5.5 2-methoxybenzylcyanide + H2O at 2% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 2-methoxyphenylacetic acid + NH3 - ? 18103 3.5.5.5 2-methoxyphenyl acetonitrile + H2O 44.5% of the activity with mandelonitrile Pseudomonas putida 2-methoxybenzoic acid + NH3 - ir 383770 3.5.5.5 2-methoxyphenylacetonitrile + 2 H2O - Alcaligenes faecalis 2-methoxyphenylacetic acid + NH3 - ? 419912 3.5.5.5 2-methoxyphenylacetonitrile + 2 H2O - Alcaligenes faecalis ZJUTB10 2-methoxyphenylacetic acid + NH3 - ? 419912 3.5.5.5 2-methyl-2-phenylpropionitrile + H2O - Pseudomonas fluorescens 2-methyl-2-phenylpropionic acid + NH3 - ? 433207 3.5.5.5 2-methyl-3-butenenitrile + H2O 3% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 454933 3.5.5.5 2-methyl-3-butenenitrile + H2O 3% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens EBC191 ? + NH3 - ? 454933 3.5.5.5 2-methyleneglutarodinitrile + H2O 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 Pseudomonas fluorescens ? + NH3 - ? 454936 3.5.5.5 2-methylglutaronitrile + 4 H2O 0.12% activity compared to phenylacetonitrile Luminiphilus syltensis 2-methylglutaric acid + 2 NH3 - ? 395579 3.5.5.5 2-methylglutaronitrile + H2O 63% activity compared to phenylacetonitrile Bradyrhizobium japonicum ? + NH3 - ? 395581 3.5.5.5 2-methylglutaronitrile + H2O activity is 9.6% compared to activity with mandelonitrile Pseudomonas psychrotolerans 2-methylglutarate + NH3 - ? 454939 3.5.5.5 2-phenylbutyronitrile + 2 H2O - Pseudomonas fluorescens 2-phenylbutyric acid + NH3 - ? 419932 3.5.5.5 2-phenylbutyronitrile + 2 H2O - Pseudomonas fluorescens EBC191 2-phenylbutyric acid + NH3 - ? 419932 3.5.5.5 2-phenylbutyronitrile + H2O 0.2% activity compared to phenylacetonitrile Luminiphilus syltensis 2-phenylbutyric acid + NH3 - ? 433221 3.5.5.5 2-phenylglycinonitrile + 2 H2O 3% activity compared to phenylacetonitrile Bradyrhizobium japonicum 2-phenylglycine + NH3 - ? 395623 3.5.5.5 2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens 2-phenylpropionic acid + NH3 - ? 383784 3.5.5.5 2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens 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 ? 383784 3.5.5.5 2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens 2-phenylpropionic acid + NH3 (R)-2-phenylpropionic acid is preferentially formed ? 383784 3.5.5.5 2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens EBC191 2-phenylpropionic acid + NH3 - ? 383784 3.5.5.5 2-phenylpropionitrile + 2 H2O - Pseudomonas fluorescens EBC191 2-phenylpropionic acid + NH3 (R)-2-phenylpropionic acid is preferentially formed ? 383784 3.5.5.5 2-phenylpropionitrile + H2O low activity, 2% activity compared to phenylacetonitrile Pseudomonas fluorescens 2-phenylpropionate + NH3 - ? 367869 3.5.5.5 2-phenylpropionitrile + H2O - Pseudomonas fluorescens ? + NH3 - ? 454942 3.5.5.5 2-phenylvaleronitrile + 2 H2O - Pseudomonas fluorescens 2-phenylvaleric acid + NH3 - ? 419935 3.5.5.5 2-phenylvaleronitrile + H2O 700% of the activity with mandelonitrile Pseudomonas fluorescens 2-phenylvaleric acid + NH3 - ? 383785 3.5.5.5 2-thiophene acetonitrile + H2O 137% of the activity with mandelonitrile Pseudomonas putida thiophene-2-carboxylic acid + NH3 - ir 383789 3.5.5.5 2-thiopheneacetonitrile + H2O - Alcaligenes faecalis 2-thiopheneacetic acid + NH3 - ? 18091 3.5.5.5 2-thiopheneacetonitrile + H2O ir, at 90% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 2-thiopheneacetic acid + NH3 not via thiopheneacetamide ? 18091 3.5.5.5 2-thiopheneacetonitrile + H2O 625% of the activity with mandelonitrile, 1.5% of product is amide Pseudomonas fluorescens 2-thiopheneacetic acid + NH3 - ? 18091 3.5.5.5 2-thiopheneacetonitrile + H2O 625% of the activity with mandelonitrile, 1.5% of product is amide Pseudomonas fluorescens EBC191 2-thiopheneacetic acid + NH3 - ? 18091 3.5.5.5 2-thiopheneacetonitrile + H2O - Alcaligenes faecalis JM3 2-thiopheneacetic acid + NH3 - ? 18091 3.5.5.5 2-trimethylsilyloxy-2-phenylacetonitrile + H2O 4% activity compared to phenylacetonitrile Bradyrhizobium japonicum 2-trimethylsilyloxy-2-phenylacetic acid + NH3 - ? 395636 3.5.5.5 3,4-(methylenedioxy)phenylacetonitrile + H2O at 65% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3,4-(methylendioxy)phenylacetic acid + NH3 - ? 18108 3.5.5.5 3,4-dichlorobenzylcyanide + H2O at 14% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3,4-dichlorophenylacetic acid + NH3 - ? 18104 3.5.5.5 3,4-dimethoxyphenylacetonitrile + H2O - Alcaligenes faecalis ? - ? 413197 3.5.5.5 3-aminopropionitrile + H2O 7% activity compared to phenylacetonitrile Bradyrhizobium japonicum 3-aminopropanoic acid + NH3 - ? 395704 3.5.5.5 3-chlorobenzylcyanide + H2O at 43% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3-chlorophenylacetic acid + NH3 - ? 18097 3.5.5.5 3-cyanopyridine + 2 H2O 208% of the rate with benzonitrile, cell extract Exophiala oligosperma nicotinic acid + NH3 - ? 141122 3.5.5.5 3-cyanopyridine + 2 H2O 208% of the rate with benzonitrile, cell extract Exophiala oligosperma R1 nicotinic acid + NH3 - ? 141122 3.5.5.5 3-cyanopyridine + 2 H2O 43.2% activity compared to phenylacetonitrile Luminiphilus syltensis pyridine 3-carboxylic acid + NH3 - ? 371827 3.5.5.5 3-cyanopyridine + H2O - Trichoderma virens Gv29-8 pyridine 3-carboxylic acid + NH3 - ? 455000 3.5.5.5 3-cyanopyridine + H2O activity is 29% compared to activity with mandelonitrile Pseudomonas psychrotolerans pyridine 3-carboxylic acid + NH3 - ? 455000 3.5.5.5 3-hexenedinitrile + H2O - Pseudomonas fluorescens ? + NH3 - ? 455006 3.5.5.5 3-hydroxyglutaronitrile + 4 H2O 0.12% activity compared to phenylacetonitrile Luminiphilus syltensis 3-hydroxyglutaric acid + 2 NH3 - ? 433250 3.5.5.5 3-hydroxyphenylpropionitrile + H2O 0.12% activity compared to phenylacetonitrile Luminiphilus syltensis 3-hydroxyphenylpropionic acid + NH3 - ? 433252 3.5.5.5 3-hydroxyphenylpropionitrile + H2O activity is 49% compared to activity with mandelonitrile Pseudomonas psychrotolerans 3-hydroxyphenylpropionic acid + NH3 - ? 433252 3.5.5.5 3-hydroxypropionitrile + H2O 1% activity compared to phenylacetonitrile Bradyrhizobium japonicum 3-hydroxypropanoate + NH3 - ? 371855 3.5.5.5 3-hydroxypropionitrile + H2O 0.07% activity compared to phenylacetonitrile Luminiphilus syltensis 3-hydroxypropionic acid + NH3 - ? 433253 3.5.5.5 3-indoleacetonitrile + H2O - Alcaligenes faecalis 3-indoleacetic acid + NH3 - ? 18090 3.5.5.5 3-indoleacetonitrile + H2O at 9% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3-indoleacetic acid + NH3 - ? 18090 3.5.5.5 3-indoleacetonitrile + H2O - Alcaligenes faecalis JM3 3-indoleacetic acid + NH3 - ? 18090 3.5.5.5 3-indoleacetonitrile + H2O at 9% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis JM3 3-indoleacetic acid + NH3 - ? 18090 3.5.5.5 3-indolylacetonitrile + H2O 2% activity compared to phenylacetonitrile Bradyrhizobium japonicum 3-indolylacetic acid + NH3 - ? 395743 3.5.5.5 3-methoxyphenylacetonitrile + 2 H2O - Alcaligenes faecalis 3-methoxyphenylacetic acid + NH3 - ? 419994 3.5.5.5 3-phenylpropionitrile + H2O - Alcaligenes faecalis 3-phenylpropionic acid + NH3 - ? 18109 3.5.5.5 3-phenylpropionitrile + H2O at 26% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3-phenylpropionic acid + NH3 - ? 18109 3.5.5.5 3-pyridineacetonitrile + H2O - Alcaligenes faecalis ? - ? 18106 3.5.5.5 3-pyridineacetonitrile + H2O at 77% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis ? - ? 18106 3.5.5.5 3-thiopheneacetonitrile + H2O - Alcaligenes faecalis 3-thiopheneacetic acid + NH3 - ? 18092 3.5.5.5 3-thiopheneacetonitrile + H2O at 24% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 3-thiopheneacetic acid + NH3 - ? 18092 3.5.5.5 3-thiopheneacetonitrile + H2O 107% of the activity with mandelonitrile, 1.5% of product is amide Pseudomonas fluorescens 3-thiopheneacetic acid + NH3 - ? 18092 3.5.5.5 3-thiopheneacetonitrile + H2O 107% of the activity with mandelonitrile, 1.5% of product is amide Pseudomonas fluorescens EBC191 3-thiopheneacetic acid + NH3 - ? 18092 3.5.5.5 3-thiopheneacetonitrile + H2O - Alcaligenes faecalis JM3 3-thiopheneacetic acid + NH3 - ? 18092 3.5.5.5 4-aminobenzylcyanide + H2O - Alcaligenes faecalis 4-aminophenylacetic acid + NH3 - ? 18099 3.5.5.5 4-aminobenzylcyanide + H2O at 44% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 4-aminophenylacetic acid + NH3 - ? 18099 3.5.5.5 4-aminobenzylcyanide + H2O high activity Alcaligenes faecalis 4-aminophenylacetic acid + NH3 - ? 18099 3.5.5.5 4-aminobenzylcyanide + H2O high activity Alcaligenes faecalis ATCC 8750 4-aminophenylacetic acid + NH3 - ? 18099 3.5.5.5 4-aminophenyl acetonitrile + H2O 502.3% of the activity with mandelonitrile Pseudomonas putida 4-aminobenzoic acid + NH3 - ir 383885 3.5.5.5 4-aminoyphenylacetonitrile + H2O - Alcaligenes faecalis ? + NH3 - ? 455031 3.5.5.5 4-aminoyphenylacetonitrile + H2O - Alcaligenes faecalis MTCC 12629 ? + NH3 - ? 455031 3.5.5.5 4-bromobenzylcyanide + H2O at 26% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis ? - ? 18089 3.5.5.5 4-bromobenzylcyanide + H2O at 26% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis JM3 ? - ? 18089 3.5.5.5 4-chlorobenzylcyanide + H2O - Alcaligenes faecalis 4-chlorophenylacetic acid + NH3 - ? 18087 3.5.5.5 4-chlorobenzylcyanide + H2O i.e. p-chlorophenylacetonitrile, best substrate Alcaligenes faecalis 4-chlorophenylacetic acid + NH3 - ? 18087 3.5.5.5 4-chlorobenzylcyanide + H2O - Alcaligenes faecalis JM3 4-chlorophenylacetic acid + NH3 - ? 18087 3.5.5.5 4-chlorobenzylcyanide + H2O i.e. p-chlorophenylacetonitrile, best substrate Alcaligenes faecalis JM3 4-chlorophenylacetic acid + NH3 - ? 18087 3.5.5.5 4-chlorobutyronitrile + H2O 59% activity compared to phenylacetonitrile Bradyrhizobium japonicum 4-chlorobutyrate + NH3 - ? 18142 3.5.5.5 4-chlorobutyronitrile + H2O 59% activity compared to phenylacetonitrile Bradyrhizobium japonicum USDA 110 4-chlorobutyrate + NH3 - ? 18142 3.5.5.5 4-chlorobutyronitrile + H2O 0.06% activity compared to phenylacetonitrile Luminiphilus syltensis 4-chlorobutyric acid + NH3 - ? 141143 3.5.5.5 4-chlorophenyl acetonitrile + H2O 360.3% of the activity with mandelonitrile Pseudomonas putida 4-chlorobenzoic acid + NH3 - ir 383890 3.5.5.5 4-cyanophenyl acetonitrile + H2O - Auricularia delicata ? - ? 455048 3.5.5.5 4-cyanophenyl acetonitrile + H2O - Aspergillus luchuensis ? - ? 455048 3.5.5.5 4-cyanophenyl acetonitrile + H2O high activity Macrophomina phaseolina ? - ? 455048 3.5.5.5 4-cyanopyridine + 2 H2O 512% of the rate with benzonitrile, cell extract Exophiala oligosperma 4-pyridinecarboxylic acid + NH3 - ? 141126 3.5.5.5 4-cyanopyridine + 2 H2O 142% activity compared to phenylacetonitrile Luminiphilus syltensis pyridine 4-carboxylic acid + NH3 - ? 371932 3.5.5.5 4-cyanopyridine + H2O - Trichoderma virens Gv29-8 pyridine 4-carboxylic acid + NH3 - ? 414101 3.5.5.5 4-cyanopyridine + H2O low activity Auricularia delicata pyridine 4-carboxylic acid + NH3 - ? 414101 3.5.5.5 4-cyanopyridine + H2O low activity Auricularia delicata TFB-10046 SS5 pyridine 4-carboxylic acid + NH3 - ? 414101 3.5.5.5 4-fluorobenzylcyanide + H2O - Alcaligenes faecalis 4-fluorophenylacetic acid + NH3 - ? 18088 3.5.5.5 4-fluorobenzylcyanide + H2O i.e. p-fluorophenylacetonitrile, at 96% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 4-fluorophenylacetic acid + NH3 - ? 18088 3.5.5.5 4-fluorobenzylcyanide + H2O - Alcaligenes faecalis JM3 4-fluorophenylacetic acid + NH3 - ? 18088 3.5.5.5 4-fluorobenzylcyanide + H2O i.e. p-fluorophenylacetonitrile, at 96% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis JM3 4-fluorophenylacetic acid + NH3 - ? 18088 3.5.5.5 4-hydroxy benzonitrile + H2O 23.1% of the activity with mandelonitrile Pseudomonas putida 4-hydroxybenzoate + NH3 - ir 383896 3.5.5.5 4-hydroxybenzylcyanide + H2O at 29% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 4-hydroxyphenylacetic acid + NH3 - ? 18101 3.5.5.5 4-hydroxycinnamonitrile + H2O 431% activity compared to phenylacetonitrile Bradyrhizobium japonicum 4-hydroxycinnamic acid + NH3 - ? 397445 3.5.5.5 4-hydroxyphenyl acetonitrile + H2O 435% of the activity with mandelonitrile Pseudomonas putida 4-hydroxybenzoic acid + NH3 - ir 383901 3.5.5.5 4-hydroxyphenylacetonitrile + H2O - Alcaligenes faecalis 4-hydroxyphenylacetic acid + NH3 - ? 395874 3.5.5.5 4-hydroxyphenylacetonitrile + H2O - Alcaligenes faecalis MTCC 12629 4-hydroxyphenylacetic acid + NH3 - ? 395874 3.5.5.5 4-hydroxyphenylacetonitrile + H2O best substrate Sinapis alba 4-hydroxyphenylacetate + NH3 - ? 403862 3.5.5.5 4-methoxybenzylcyanide + H2O at 62% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 4-methoxyphenylacetic acid + NH3 - ? 18102 3.5.5.5 4-methoxyphenylacetonitrile + 2 H2O - Alcaligenes faecalis 4-methoxyphenylacetic acid + NH3 - ? 420055 3.5.5.5 4-methoxyphenylacetonitrile + H2O 81% of the activity with 4-hydroxyphenylacetonitrile Sinapis alba 4-methoxyphenylacetate + NH3 - ? 403880 3.5.5.5 4-nitrobenzylcyanide + H2O - Alcaligenes faecalis 4-nitrophenylacetate + NH3 - ? 18100 3.5.5.5 4-nitrobenzylcyanide + H2O at 45% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis 4-nitrophenylacetate + NH3 - ? 18100 3.5.5.5 4-phenylbutyronitrile + H2O 86% activity compared to phenylacetonitrile Bradyrhizobium japonicum 4-phenylbutyrate + NH3 - ? 395920 3.5.5.5 acrylonitrile + H2O - Alcaligenes faecalis propenoic acid + NH3 - ? 18111 3.5.5.5 acrylonitrile + H2O at 7% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis propenoic acid + NH3 - ? 18111 3.5.5.5 acrylonitrile + H2O 121% of the rate with benzonitrile, cell extract Exophiala oligosperma acrylic acid + NH3 - ? 18118 3.5.5.5 acrylonitrile + H2O 0.05% activity compared to phenylacetonitrile Luminiphilus syltensis acrylic acid + NH3 - ? 18118 3.5.5.5 acrylonitrile + H2O 121% of the rate with benzonitrile, cell extract Exophiala oligosperma R1 acrylic acid + NH3 - ? 18118 3.5.5.5 acrylonitrile + H2O 0.05% activity compared to phenylacetonitrile Luminiphilus syltensis NOR5-1B acrylic acid + NH3 - ? 18118 3.5.5.5 acrylonitrile + H2O 5% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 455245 3.5.5.5 adiponitrile + H2O 17.2% of the activity with mandelonitrile Pseudomonas putida adipic acid + NH3 - ir 18148 3.5.5.5 adiponitrile + H2O 3% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 455270 3.5.5.5 allyl cyanide + NH3 11% activity compared to phenylacetonitrile Bradyrhizobium japonicum 3-butenoic acid + NH3 - ? 396377 3.5.5.5 allylcyanide + H2O 12% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 455285 3.5.5.5 alpha-methylphenylacetonitrile + H2O 0.14% activity compared to phenylacetonitrile Luminiphilus syltensis alpha-methylphenylacetic acid + NH3 - ? 433407 3.5.5.5 alpha-methylphenylacetonitrile + H2O activity is 88% compared to activity with mandelonitrile Pseudomonas psychrotolerans alpha-methylphenylacetic acid + NH3 - ? 433407 3.5.5.5 Arylacetonitrile + H2O pathway in nitrile catabolism, inducible enzyme Alcaligenes faecalis ? - ? 369563 3.5.5.5 benzonitrile + 2 H2O activity is 64% compared to activity with mandelonitrile Pseudomonas psychrotolerans benzoate + NH3 - ? 18154 3.5.5.5 benzonitrile + 2 H2O activity is 64% compared to activity with mandelonitrile Pseudomonas psychrotolerans L19 benzoate + NH3 - ? 18154 3.5.5.5 benzonitrile + 2 H2O - Exophiala oligosperma benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + 2 H2O - Trichoderma virens Gv29-8 benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + 2 H2O low activity Alcaligenes faecalis benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + 2 H2O 21% activity compared to phenylacetonitrile Luminiphilus syltensis benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + 2 H2O - Exophiala oligosperma R1 benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + 2 H2O low activity Alcaligenes faecalis ATCC 8750 benzoic acid + NH3 - ? 141120 3.5.5.5 benzonitrile + H2O 1% activity compared to phenylacetonitrile Bradyrhizobium japonicum benzoic acid + NH3 - ? 396573 3.5.5.5 benzylcyanide + H2O - Alcaligenes faecalis phenylacetic acid + NH3 - ? 18093 3.5.5.5 benzylcyanide + H2O at 53% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis phenylacetic acid + NH3 - ? 18093 3.5.5.5 cinnamonitrile + H2O 0.07% activity compared to phenylacetonitrile Luminiphilus syltensis cinnamic acid + NH3 - ? 433572 3.5.5.5 crotononitrile + 2 H2O 4% activity compared to phenylacetonitrile Bradyrhizobium japonicum crotonic acid + NH3 - ? 372778 3.5.5.5 cyanophenyl acetonitrile + H2O - Trichoderma virens Gv29-8 ? - ? 455488 3.5.5.5 cyclohexane carbonitrile + H2O 12.5% of the activity with mandelonitrile Pseudomonas putida cyclohexlycarboxylic acid + NH3 - ir 384489 3.5.5.5 diphenylacetonitrile + H2O - Alcaligenes sp. diphenylacetic acid + NH3 - ? 433644 3.5.5.5 diphenylacetonitrile + H2O - Alcaligenes sp. MTCC 10675 diphenylacetic acid + NH3 - ? 433644 3.5.5.5 dodecanenitrile + H2O 0.04% activity compared to phenylacetonitrile Luminiphilus syltensis dodecanoic acid + NH3 - ? 433657 3.5.5.5 fumarodinitrile + H2O 11% compared to the activity with 3-hexenedinitrile. Fumarodinitrile is converted to the monocarboxylate and the monocarboxamide in a ratio of about 65:35 Pseudomonas fluorescens 3-cyanoacrylamide + 3-cyanoacrylic acid + NH3 - ? 455676 3.5.5.5 fumaronitrile + H2O - Auricularia delicata fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Aspergillus luchuensis fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Macrophomina phaseolina fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Trichoderma virens Gv29-8 fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O 0.72% activity compared to phenylacetonitrile Luminiphilus syltensis fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Macrophomina phaseolina MS6 fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Auricularia delicata TFB-10046 SS5 fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O 0.72% activity compared to phenylacetonitrile Luminiphilus syltensis NOR5-1B fumaric acid + NH3 - ? 18124 3.5.5.5 fumaronitrile + H2O - Aspergillus luchuensis IFO 4308 fumaric acid + NH3 - ? 18124 3.5.5.5 glycolonitrile + H2O 0.08% activity compared to phenylacetonitrile Luminiphilus syltensis glycolic acid + NH3 - ? 433769 3.5.5.5 heptanenitrile + H2O 107% activity compared to phenylacetonitrile Bradyrhizobium japonicum heptanoic acid + NH3 - ? 397412 3.5.5.5 hex-5-enenitrile + H2O 7.9% of the activity with mandelonitrile Pseudomonas putida hex-5-enoic acid + NH3 - ir 383978 3.5.5.5 hexanenitrile + H2O 60% activity compared to phenylacetonitrile Bradyrhizobium japonicum hexanoic acid + NH3 - ? 397422 3.5.5.5 hydroxy(2-methoxyphenyl)acetonitrile + H2O 178% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-hydroxy(2-methoxyphenyl)acetic acid + NH3 - ? 433824 3.5.5.5 hydroxy(2-methylphenyl)acetonitrile + H2O 194% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-hydroxy(2-methylphenyl)acetic acid + NH3 - ? 433825 3.5.5.5 hydroxy(phenyl)acetonitrile + H2O 404% activity compared to phenylacetonitrile Luminiphilus syltensis (2R)-hydroxy(phenyl)acetic acid + NH3 - ? 433828 3.5.5.5 iminodiacetonitrile + 2 H2O 0.05% activity compared to phenylacetonitrile Luminiphilus syltensis iminodiacetic acid + 2 NH3 - ? 18153 3.5.5.5 iminodiacetonitrile + 2 H2O 0.05% activity compared to phenylacetonitrile Luminiphilus syltensis NOR5-1B iminodiacetic acid + 2 NH3 - ? 18153 3.5.5.5 indole 3-acetonitrile + H2O 319.9% of the activity with mandelonitrile Pseudomonas putida (indol-3-yl)acetic acid + NH3 - ir 384911 3.5.5.5 indole-3-acetonitrile + H2O - Pseudomonas syringae pv. syringae indole-3-acetic acid + NH3 - ? 370990 3.5.5.5 indole-3-acetonitrile + H2O 22% of the activity with mandelonitrile, 0.1% of product is amide Pseudomonas fluorescens indole-3-acetic acid + NH3 - ? 370990 3.5.5.5 indole-3-acetonitrile + H2O 35% activity compared to phenylacetonitrile Luminiphilus syltensis indole-3-acetic acid + NH3 - ? 370990 3.5.5.5 indole-3-acetonitrile + H2O - Pseudomonas syringae pv. syringae B728a indole-3-acetic acid + NH3 - ? 370990 3.5.5.5 isovaleronitrile + H2O 11.4% of the activity with mandelonitrile Pseudomonas putida isovaleric acid + NH3 - ir 384948 3.5.5.5 m-tolylacetonitrile + H2O - Alcaligenes faecalis m-tolylacetic acid + NH3 - ? 18095 3.5.5.5 m-tolylacetonitrile + H2O at 32% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis m-tolylacetic acid + NH3 - ? 18095 3.5.5.5 m-xylenedicyanide + H2O at 2.7% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis ? - ? 18110 3.5.5.5 malononitrile + H2O 3.7% activity compared to phenylacetonitrile Luminiphilus syltensis malonic acid + NH3 - ? 18145 3.5.5.5 malononitrile + H2O 3.7% activity compared to phenylacetonitrile Luminiphilus syltensis NOR5-1B malonic acid + NH3 - ? 18145 3.5.5.5 mandelonitrile + 2 H2O - Alcaligenes faecalis mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Pseudomonas fluorescens mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Alcaligenes sp. mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Pseudomonas fluorescens mandelic acid + NH3 slight preference for the formation of (R)-mandelic acid ? 18107 3.5.5.5 mandelonitrile + 2 H2O at 8% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O 31% enantiomeric excess for R-configuration in acid formation, 19% of product is amide with 85% enantiomeric excess for S-configuration Pseudomonas fluorescens mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O 4% activity compared to phenylacetonitrile Bradyrhizobium japonicum mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O best substrate, 164% activity compared to phenylacetonitrile Luminiphilus syltensis mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Pseudomonas fluorescens EBC191 mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O 31% enantiomeric excess for R-configuration in acid formation, 19% of product is amide with 85% enantiomeric excess for S-configuration Pseudomonas fluorescens EBC191 mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Pseudomonas fluorescens EBC191 mandelic acid + NH3 slight preference for the formation of (R)-mandelic acid ? 18107 3.5.5.5 mandelonitrile + 2 H2O 4% activity compared to phenylacetonitrile Bradyrhizobium japonicum USDA 110 mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O best substrate, 164% activity compared to phenylacetonitrile Luminiphilus syltensis NOR5-1B mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Alcaligenes sp. MTCC 10675 mandelic acid + NH3 - ? 18107 3.5.5.5 mandelonitrile + 2 H2O - Pseudomonas putida (R)-mandelic acid + NH3 99.9% enantiomeric excess for (R)-isomer ir 385125 3.5.5.5 mandelonitrile + 2 H2O racemic, enzyme hydrolizes the cyanide functionality to the corresponding carboxylic acid under ambient conditions Pseudomonas putida (R)-mandelic acid + NH3 - ? 385125 3.5.5.5 mandelonitrile + 2 H2O racemic, enzyme hydrolizes the cyanide functionality to the corresponding carboxylic acid under ambient conditions Pseudomonas putida MTCC 5110 (R)-mandelic acid + NH3 - ? 385125 3.5.5.5 mandelonitrile + 2 H2O - Alcaligenes faecalis mandelate + NH3 - ? 419456 3.5.5.5 mandelonitrile + 2 H2O - Alcaligenes faecalis ZJUTB10 mandelate + NH3 - ? 419456 3.5.5.5 mandelonitrile + H2O - Alcaligenes faecalis mandelic acid + NH3 - ? 455995 3.5.5.5 mandelonitrile + H2O - Alcaligenes faecalis MTCC 12629 mandelic acid + NH3 - ? 455995 3.5.5.5 methylthioacetonitrile + H2O 72% activity compared to phenylacetonitrile Bradyrhizobium japonicum methylthioacetic acid + NH3 - ? 397770 3.5.5.5 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 Alcaligenes faecalis ? - ? 89 3.5.5.5 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 Pseudomonas fluorescens ? - ? 89 3.5.5.5 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 Pseudomonas fluorescens ? - ? 89 3.5.5.5 additional information does not use 2-(N,N-dimethylamino)-2-phenylacetonitrile, 2-phenylpropionitrile, and 2-phenylbutyronitrile as substrate Bradyrhizobium japonicum ? - ? 89 3.5.5.5 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 Exophiala oligosperma ? - ? 89 3.5.5.5 additional information enzyme requires an oxygen atom in para-position of the substrate. Indole-3-acetonitrile, arylcyanides, and arylpropionitriles are poor substrates Sinapis alba ? - ? 89 3.5.5.5 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 Pseudomonas fluorescens ? - ? 89 3.5.5.5 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 Alcaligenes faecalis ? - ? 89 3.5.5.5 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 Alcaligenes sp. ? - ? 89 3.5.5.5 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 Pseudomonas psychrotolerans ? - - 89 3.5.5.5 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, Pseudomonas fluorescens ? - - 89 3.5.5.5 additional information very low activity with: (R,S)-Mandelonitrile Trichoderma virens Gv29-8 ? - - 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine Auricularia delicata ? - - 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine Aspergillus luchuensis ? - - 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine Macrophomina phaseolina ? - - 89 3.5.5.5 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 Pseudomonas fluorescens EBC191 ? - ? 89 3.5.5.5 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 Pseudomonas fluorescens EBC191 ? - ? 89 3.5.5.5 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, Pseudomonas fluorescens EBC191 ? - - 89 3.5.5.5 additional information does not use 2-(N,N-dimethylamino)-2-phenylacetonitrile, 2-phenylpropionitrile, and 2-phenylbutyronitrile as substrate Bradyrhizobium japonicum USDA 110 ? - ? 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine Macrophomina phaseolina MS6 ? - - 89 3.5.5.5 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 Exophiala oligosperma R1 ? - ? 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine Auricularia delicata TFB-10046 SS5 ? - - 89 3.5.5.5 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 Alcaligenes faecalis ZJUTB10 ? - ? 89 3.5.5.5 additional information very low activity with: benzonitrile, 2-cyanopyridine, 3-cyanopyridine, 4-cyanopyridine Aspergillus luchuensis IFO 4308 ? - - 89 3.5.5.5 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 Alcaligenes sp. MTCC 10675 ? - ? 89 3.5.5.5 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 Alcaligenes faecalis JM3 ? - ? 89 3.5.5.5 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 Pseudomonas psychrotolerans L19 ? - - 89 3.5.5.5 n-butyronitrile + H2O 15% activity compared to phenylacetonitrile Bradyrhizobium japonicum n-butyric acid + NH3 - ? 141137 3.5.5.5 n-butyronitrile + H2O 15% activity compared to phenylacetonitrile Bradyrhizobium japonicum USDA 110 n-butyric acid + NH3 - ? 141137 3.5.5.5 o-tolylacetonitrile + H2O - Alcaligenes faecalis o-tolylacetic acid + NH3 - ? 18096 3.5.5.5 o-tolylacetonitrile + H2O at 4% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis o-tolylacetic acid + NH3 - ? 18096 3.5.5.5 octanedinitrile + H2O 0.14% activity compared to phenylacetonitrile Luminiphilus syltensis ? + NH3 - ? 434080 3.5.5.5 p-tolylacetonitrile + H2O at 72% the rate of 4-chlorobenzylcyanide hydrolysis Alcaligenes faecalis p-tolylacetic acid + NH3 - ? 18094 3.5.5.5 phenoxy acetonitrile + H2O 232.6% of the activity with mandelonitrile Pseudomonas putida phenoxyacetate + NH3 - ir 385529 3.5.5.5 phenyl acetonitrile + H2O 342.3% of the activity with mandelonitrile Pseudomonas putida benzoic acid + NH3 - ir 385532 3.5.5.5 phenyl glycinenitrile + H2O 192.5% of the activity with mandelonitrile Pseudomonas putida phenylalanine + NH3 - ir 385534 3.5.5.5 phenyl thioacetonitrile + H2O 187.7% of the activity with mandelonitrile Pseudomonas putida thiophenylacetate + NH3 - ir 385535 3.5.5.5 phenylacetonitrile + 2 H2O - Alcaligenes faecalis phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Neurospora crassa phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Pseudomonas putida phenylacetate + NH3 - ir 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Aspergillus niger phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Auricularia delicata phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Aspergillus luchuensis phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Macrophomina phaseolina phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Trichoderma virens Gv29-8 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O best substrate Pseudomonas fluorescens phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O preferred substrate Neurospora crassa phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O preferred substrate Aspergillus niger phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O 22% of the rate with benzonitrile, cell extract Exophiala oligosperma phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O activity is 404% compared to activity with mandelonitrile Pseudomonas psychrotolerans phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Macrophomina phaseolina MS6 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O 22% of the rate with benzonitrile, cell extract Exophiala oligosperma R1 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Alcaligenes faecalis MTCC 12629 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Auricularia delicata TFB-10046 SS5 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Aspergillus luchuensis IFO 4308 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Aspergillus niger CBS 513.88 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O preferred substrate Aspergillus niger CBS 513.88 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Neurospora crassa OR74A phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O preferred substrate Neurospora crassa OR74A phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O activity is 404% compared to activity with mandelonitrile Pseudomonas psychrotolerans L19 phenylacetate + NH3 - ? 18172 3.5.5.5 phenylacetonitrile + 2 H2O - Alcaligenes faecalis phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O best substrate Alcaligenes sp. phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O 100% activity Bradyrhizobium japonicum phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O 206% of the activity with mandelonitrile, 3.9% of product is amide Pseudomonas fluorescens phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O 206% of the activity with mandelonitrile, 3.9% of product is amide Pseudomonas fluorescens EBC191 phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O 100% activity Bradyrhizobium japonicum USDA 110 phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O - Alcaligenes faecalis ZJUTB10 phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + 2 H2O best substrate Alcaligenes sp. MTCC 10675 phenylacetic acid + NH3 - ? 363353 3.5.5.5 phenylacetonitrile + H2O - Alcaligenes faecalis ? - ? 413531 3.5.5.5 phenylpropionitrile + 2 H2O - Pseudomonas syringae pv. syringae phenylpropionic acid + NH3 - ? 374311 3.5.5.5 phenylpropionitrile + 2 H2O - Pseudomonas syringae pv. syringae B728a phenylpropionic acid + NH3 - ? 374311 3.5.5.5 phenylpropionitrile + 2 H2O - Neurospora crassa phenylpropionate + NH3 - ? 421204 3.5.5.5 phenylpropionitrile + 2 H2O - Aspergillus niger phenylpropionate + NH3 - ? 421204 3.5.5.5 phenylpropionitrile + 2 H2O - Aspergillus niger CBS 513.88 phenylpropionate + NH3 - ? 421204 3.5.5.5 phenylpropionitrile + 2 H2O - Neurospora crassa OR74A phenylpropionate + NH3 - ? 421204 3.5.5.5 rac 2-(methoxy)-mandelonitrile + H2O - Pseudomonas fluorescens (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% ? 367868 3.5.5.5 succinonitrile + H2O 0.12% activity compared to phenylacetonitrile Luminiphilus syltensis succinic acid + NH3 - ? 374665 3.5.5.5 valeronitrile + H2O 12.5% of the activity with mandelonitrile Pseudomonas fluorescens valeric acid + NH3 - ? 385908 3.5.5.5 valeronitrile + H2O 57% activity compared to phenylacetonitrile Bradyrhizobium japonicum valeric acid + NH3 - ? 385908 3.5.5.5 valeronitrile + H2O 0.08% activity compared to phenylacetonitrile Luminiphilus syltensis valeric acid + NH3 - ? 385908 3.5.5.5 valeronitrile + H2O 25% compared to the activity with 3-hexenedinitrile Pseudomonas fluorescens ? + NH3 - ? 456933