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Literature summary for 3.5.5.5 extracted from

  • Baum, S.; Williamson, D.S.; Sewell, T.; Stolz, A.
    Conversion of sterically demanding alpha,alpha-disubstituted phenylacetonitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191 (2012), Appl. Environ. Microbiol., 78, 48-57.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.5.5.5

Application

Application Comment Organism
synthesis recombinant cells expressing the enzyme are promising catalysts for the synthesis of stable chiral quaternary carbon centers from ketones Pseudomonas fluorescens

Cloned(Commentary)

Cloned (Comment) Organism
expression under the control of a rhamnose-inducible promoter in Escherichia coli strain JM109 Pseudomonas fluorescens

Protein Variants

Protein Variants Comment Organism
Tyr54C the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Tyr54P the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Tyr54V the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Y54A the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Y54F the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Y54H the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Y54I inactive Pseudomonas fluorescens
Y54K inactive Pseudomonas fluorescens
Y54L mutant with significantly reduced activity compared to the wild type enzyme Pseudomonas fluorescens
Y54M the mutant shows wild type activity but forms significantly decreased relative amounts of atrolactamide from 2-hydroxy-2-phenylpropionitrile Pseudomonas fluorescens
Y54R inactive Pseudomonas fluorescens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information kinetic and chiral analysis, overview Pseudomonas fluorescens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O Pseudomonas fluorescens
-
 2-acetyloxy-2-methylphenylacetic acid + NH3
-
 ?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O Pseudomonas fluorescens EBC191
-
 2-acetyloxy-2-methylphenylacetic acid + NH3
-
 ?

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens
-
-
-
Pseudomonas fluorescens EBC191
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
-
 Pseudomonas fluorescens 2-acetyloxy-2-methylphenylacetic acid + NH3
-
 ?
2-acetyloxy-2-methylphenylacetonitrile + 2 H2O
-
 Pseudomonas fluorescens EBC191 2-acetyloxy-2-methylphenylacetic acid + NH3
-
 ?
2-acetyloxy-2-methylphenylacetonitrile + H2O
-
 Pseudomonas fluorescens 2-acetyloxy-2-methylphenylacetic acid + NH3
-
 ?
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 ?
2-methyl-2-phenylpropionitrile + H2O
-
 Pseudomonas fluorescens 2-methyl-2-phenylpropionic acid + NH3
-
 ?
2-phenylbutyronitrile + 2 H2O
-
 Pseudomonas fluorescens 2-phenylbutyric acid + NH3
-
 ?
2-phenylbutyronitrile + 2 H2O
-
 Pseudomonas fluorescens EBC191 2-phenylbutyric acid + NH3
-
 ?
2-phenylpropionitrile + 2 H2O
-
 Pseudomonas fluorescens 2-phenylpropionic acid + NH3
-
 ?
2-phenylpropionitrile + 2 H2O
-
 Pseudomonas fluorescens EBC191 2-phenylpropionic acid + NH3
-
 ?
2-phenylvaleronitrile + 2 H2O
-
 Pseudomonas fluorescens 2-phenylvaleric acid + NH3
-
 ?
mandelonitrile + 2 H2O
-
 Pseudomonas fluorescens mandelic acid + NH3
-
 ?
mandelonitrile + 2 H2O
-
 Pseudomonas fluorescens EBC191 mandelic acid + NH3
-
 ?
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 ?
-
 ?
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 ?
-
 ?

Synonyms

Synonyms Comment Organism
Arylacetonitrilase
-
 Pseudomonas fluorescens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at Pseudomonas fluorescens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
4.5
-
 assay at Pseudomonas fluorescens
7
-
-
 Pseudomonas fluorescens