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Information on EC 3.5.5.1 - nitrilase and Organism(s) Arabidopsis thaliana and UniProt Accession P32962

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EC Tree
     3 Hydrolases
         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
             3.5.5 In nitriles
                3.5.5.1 nitrilase
IUBMB Comments
Acts on a wide range of aromatic nitriles including (indol-3-yl)acetonitrile, and also on some aliphatic nitriles, and on the corresponding acid amides. cf. EC 4.2.1.84 nitrile hydratase.
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This record set is specific for:
Arabidopsis thaliana
UNIPROT: P32962
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Word Map
The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
nitrilase, nitrilase 1, cyc705, nitrilase bll6402, nlase, nitrile aminohydrolase, benzonitrilase a, nitras-atii, nitmc-fb, nitrilase i, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
acetonitrilase
-
-
-
-
Arylacetonitrilase
-
-
-
-
auxin-producing nitrilase
-
benzonitrilase
-
-
-
-
nirilase II
-
-
nitrilase 1
nitrilase AtNIT1
-
-
additional information
the enzyme belong to the nitrilase superfamily, branch 1.1 auxin-producing nitrilase, overview
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a nitrile + 2 H2O = a carboxylate + NH3
show the reaction diagram
a nitrile + 2 H2O = a carboxylate + NH3
show the reaction diagram
enzyme structure and reaction mechanism
SYSTEMATIC NAME
IUBMB Comments
nitrile aminohydrolase
Acts on a wide range of aromatic nitriles including (indol-3-yl)acetonitrile, and also on some aliphatic nitriles, and on the corresponding acid amides. cf. EC 4.2.1.84 nitrile hydratase.
CAS REGISTRY NUMBER
COMMENTARY hide
157297-79-5
Arabidopsis thaliana columbiana and Lansberg gene NIT2
157575-01-4
Arabidopsis thaliana columbiana gene NIT3
157575-02-5
Arabidopsis thaliana columbiana gene NIT4
205331-43-7
Arabidopsis thaliana nit2 isoenzyme2
205394-78-1
Arabidopsis thaliana nit3 isoenzyme3
205394-80-5
Arabidopsis thaliana nit1 isoenzyme1
9024-90-2
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
phenylacetonitrile + 2 H2O
phenylacetate + NH3
show the reaction diagram
-
-
-
?
(3S)-isobutylsuccinonitrile + H2O
(3S)-3-cyano-5-methyl hexanoic acid
show the reaction diagram
-
specific for the (3S)-isomer
-
-
?
(methylthio)acetonitrile + H2O
(methylthio)acetic acid + NH3
show the reaction diagram
-
-
-
?
(methylthio)acetonitrile + H2O
2-(methylthio)acetic acid + NH3
show the reaction diagram
-
-
-
?
(phenylthio)acetonitrile + H2O
2-(phenylthio)acetic acid + NH3
show the reaction diagram
-
-
-
?
1-(cyanoacetyl)pyrrolidine + H2O
? + NH3
show the reaction diagram
low activity
-
-
?
2-cyanopyridine + 2 H2O
pyridine 2-carboxylic acid + NH3
show the reaction diagram
low activity
-
-
?
3-cyanopyridine + 2 H2O
pyridine 3-carboxylic acid + NH3
show the reaction diagram
low activity
-
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropanoate + NH3
show the reaction diagram
3-phenylpropanenitrile + H2O
phenylacetic acid + NH3
show the reaction diagram
-
-
-
-
?
3-phenylpropionitrile + H2O
3-phenylpropionic acid + NH3
show the reaction diagram
the enzyme has 270times more activity with 3-phenylpropionitrile than that observed with benzonitrile
-
-
?
3-trans-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]prop-2-enenitrile + H2O
(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid + NH3
show the reaction diagram
-
-
-
-
?
4-hydroxybenzylcyanide + H2O
4-hydroxybenzoic acid + NH3
show the reaction diagram
low activity
-
-
?
4-phenylbutyronitrile + H2O
4-phenylbutyric acid + NH3
show the reaction diagram
-
-
-
?
allyl cyanide + H2O
prop-2-enoic acid + NH3
show the reaction diagram
benzonitrile + 2 H2O
benzoic acid + NH3
show the reaction diagram
-
-
-
?
chloroacetonitrile + H2O
chloroacetic acid + NH3
show the reaction diagram
low activity
-
-
?
cyclopropanecarbonitrile + H2O
cyclopropanecarboxylic acid + NH3
show the reaction diagram
-
-
-
?
hydrocinnamonitrile + H2O
hydrocinnamic acid + NH3
show the reaction diagram
-
-
-
-
?
indol-3-acetonitrile + H2O
indol-3-acetic acid + NH3
show the reaction diagram
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
show the reaction diagram
phenylacetonitrile + 2 H2O
phenylacetic acid + NH3
show the reaction diagram
low activity
-
-
?
phenylbutyronitrile + H2O
phenylbutyric acid + NH3
show the reaction diagram
phenylpropionitrile + 2 H2O
phenylpropionic acid + NH3
show the reaction diagram
propionitrile + H2O
propionic acid + NH3
show the reaction diagram
trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile + H2O
trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylic acid + NH3
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
indol-3-acetonitrile + H2O
indol-3-acetic acid + NH3
show the reaction diagram
indole-3-acetonitrile + H2O
indole-3-acetic acid + NH3
show the reaction diagram
-
isozymes are involved in indole-3-acetic acid production
-
-
?
additional information
?
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
phenylacetonitrile
pH 8.0, 30°C, isozyme NIT2
0.88 - 1.31
(methylthio)acetonitrile
0.6 - 6.27
allyl cyanide
1.75 - 30.1
indole-3-acetonitrile
0.14 - 0.23
phenylacetonitrile
0.07 - 0.09
phenylbutyronitrile
0.22 - 0.43
phenylpropionitrile
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15
with substrate indole-3-acetonitrile
35 - 40
with substrate phenylpropionitrile
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isozyme NIT2
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
predominant isoform NIT2 in developing embryos
Manually annotated by BRENDA team
predominant isoform NIT2 in germinating seeds
Manually annotated by BRENDA team
-
2 forms, nitrilase I and II
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
nitrilase II
-
Manually annotated by BRENDA team
-
nitrilase II, tightly associated
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
Arabidopsis nit1 knockout lines display a loss in the production of deaminated glutathione with accumulation of higher levels of the glutathione breakdown products cysteinylglycine and cystathionine
metabolism
use of script based method for classification of aliphatic and aromatic group of nitrilases. The algorithm can be used as a tool to classify nitrilases as aliphatic and aromatic class. The overall accuracy achieved is 95.00%. These machine learning techniques can be used to predict different features of the gene/protein and selection of these algorithms for the prediction of gene/protein function
physiological function
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
NRL2_ARATH
339
0
37153
Swiss-Prot
other Location (Reliability: 4)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
440000
-
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dodecamer
-
gel filtration
homododecamer
14 * 38000
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
side-chain modification
under stress conditions the enzyme undergoes spontaneous thiolation with GSSG-biotin through modification of the active-site cysteines
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C179A
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
C179N
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
A200G
-
37% increased activity compared to the wild type enzyme
C180A
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
C180N
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
C186A
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
C186N
site-directed mutagenesis, completely inactive mutant, determined with substrate indole-3-acetonitrile
C236S
-
mutant has a nearly 3fold increase in reactivity
H101Q/C239S/D246E
-
47% increased activity compared to the wild type enzyme
I29L
-
113% increased activity compared to the wild type enzyme
P172S/C236S/V291I
-
84% increased activity compared to the wild type enzyme
R89S/G179G
-
89% increased activity compared to the wild type enzyme
T28S
-
30% increased activity compared to the wild type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA resin chromatography and Superdex 75 gel filtration
-
nitrilase II, to homogeneity, recombinant enzyme
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination, genes of the 3 isozymes are clustered on chromosome 3
-
expressed in Escherichia coli
-
expressed in Escherichia coli strains BL21 (DE3), BRLplys (DE3), Rosetta (DE3), and Tuner (DE3)
-
expression in Escherichia coli
-
RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
release from insoluble inclusion bodies after treatment with Triton X-114
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Grsic-Rausch, S.; Kobelt, P.; Siemens, J.M.; Bischoff, M.; Ludwig-Muller, J.
Expression and localization of nitrilase during symptom development of the clubroot disease in Arabidopsis
Plant Physiol.
122
369-378
2000
Arabidopsis thaliana
Manually annotated by BRENDA team
Bartling, D.; Seedorf, M.; Schmidt, R.C.; Weiler, E.W.
Molecular characterization of two cloned nitrilases from Arabidopsis thaliana: Key enzymes in biosynthesis of the plant hormone indole-3-acetic acid
Proc. Natl. Acad. Sci. USA
91
6021-6025
1994
Arabidopsis thaliana
Manually annotated by BRENDA team
Bartling, D.; Seedorf, M.; Mithfer, A.; Weiler, E.W.
Cloning and expression of an Arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid
Eur. J. Biochem.
205
417-424
1992
Arabidopsis thaliana
Manually annotated by BRENDA team
O'Reilly, C.; Turner, P.D.
The nitrilase family of CN hydrolyzing enzymes - a comparative study
J. Appl. Microbiol.
95
1161-1174
2003
Acidovorax facilis, Acidovorax facilis 72W, Acinetobacter sp., Acinetobacter sp. AK226, Aeribacillus pallidus, Aeribacillus pallidus Dac521, Alcaligenes faecalis, Alcaligenes faecalis JM3, Arabidopsis thaliana, Bacillus sp. (in: Bacteria), Bacillus sp. (in: Bacteria) OxB-1, Brassica rapa, Comamonas testosteroni, Fusarium oxysporum, Fusarium solani, Fusarium solani IMI196840, Hordeum vulgare, Klebsiella pneumoniae, Nocardia sp., Pseudomonas sp., Rhodococcus rhodochrous, Rhodococcus rhodochrous K22, Rhodococcus sp., Rhodococcus sp. ATCC 39484
Manually annotated by BRENDA team
Brenner, C.
Catalysis in the nitrilase superfamily
Curr. Opin. Struct. Biol.
12
775-782
2002
Arabidopsis thaliana (P32961), Homo sapiens (Q86X76)
Manually annotated by BRENDA team
Vorwerk, S.; Biernacki, S.; Hillebrand, H.; Janzik, I.; Muller, A.; Weiler, E.W.; Piotrowski, M.
Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster
Planta
212
508-516
2001
Arabidopsis thaliana (P32961), Arabidopsis thaliana (P32962), Arabidopsis thaliana (P46010), Arabidopsis thaliana
Manually annotated by BRENDA team
Yildirim, S.; Ruinatscha, R.; Gross, R.; Wohlgemuth, R.; Kohler, H.E.; Witholt, B.; Schmid, A.
Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles
J. Mol. Catal. B
38
76-83
2006
Arabidopsis thaliana, Rhodococcus sp.
-
Manually annotated by BRENDA team
Dixon, D.P.; Skipsey, M.; Grundy, N.M.; Edwards, R.
Stress-induced protein S-glutathionylation in Arabidopsis
Plant Physiol.
138
2233-2244
2005
Arabidopsis thaliana (P32961)
Manually annotated by BRENDA team
Singh, R.; Sharma, R.; Tewari, N.; Tewari, N.; Rawat, D.S.
Nitrilase and its application as a green catalyst
Chem. Biodivers.
3
1279-1287
2006
Acidovorax facilis, Acidovorax facilis 72W, Acinetobacter sp., Acinetobacter sp. AK226, Aeribacillus pallidus, Aeribacillus pallidus Dac521, Alcaligenes faecalis, Arabidopsis thaliana, Bacillus sp. (in: Bacteria), Bacillus sp. (in: Bacteria) OxB-1, Comamonas testosteroni, Fusarium oxysporum, Fusarium solani, Fusarium solani IMI196840, Hordeum vulgare, Klebsiella pneumoniae, Penicillium multicolor, Pseudomonas sp., Rhodococcus rhodochrous, Rhodococcus rhodochrous K22, Rhodococcus sp.
Manually annotated by BRENDA team
Yazbeck, D.R.; Durao, P.J.; Xie, Z.; Tao, J.
A metal ion-based method for the screening of nitrilases
J. Mol. Catal. B
39
156-159
2006
Arabidopsis thaliana
-
Manually annotated by BRENDA team
Xie, Z.; Feng, J.; Garcia, E.; Bernett, M.; Yazbeck, D.; Tao, J.
Cloning and optimization of a nitrilase for the synthesis of (3S)-3-cyano-5-methyl hexanoic acid
J. Mol. Catal. B
41
75-80
2006
Arabidopsis thaliana
-
Manually annotated by BRENDA team
Thuku, R.; Brady, D.; Benedik, M.; Sewell, B.
Microbial nitrilases: Versatile, spiral forming, industrial enzymes
J. Appl. Microbiol.
106
703-727
2009
Aeribacillus pallidus (Q0PIV8), Aeribacillus pallidus Dac521 (Q0PIV8), Arabidopsis thaliana (P32961), Arthrobacter sp., Aspergillus niger (A9QXE0), Aspergillus niger K10 (A9QXE0), Bradyrhizobium japonicum, Bradyrhizobium japonicum USDA 110, Brassica napus, Fusarium oxysporum f. sp. melonis, Fusarium solani, Fusarium solani IMI 196840, Fusarium solani O1, Rhodococcus rhodochrous, Rhodococcus rhodochrous ATCC 39484, Rhodococcus rhodochrous PA-34, Rhodococcus sp., Rhodococcus sp. NCIMB 11215, Rhodococcus sp. NCIMB 11216
Manually annotated by BRENDA team
Jez, J.
Plant nitrilase A new job for an old enzyme
Biochem. J.
476
1105-1107
2019
Arabidopsis thaliana (P32961), Arabidopsis thaliana
Manually annotated by BRENDA team
Sharma, N.; Verma, R.; Savitri, R.; Bhalla, T.C.
Classifying nitrilases as aliphatic and aromatic using machine learning technique
3 Biotech
8
68
2018
Aeribacillus pallidus, Arabidopsis thaliana (P46010), Arenibacter latericius, Bacillus sp. OxB-1 (P82605), Blastomyces dermatitidis, Blastomyces dermatitidis ER-3, Bordetella bronchiseptica (A0A0H3LIT0), Burkholderia cenocepacia (B4EE44), Burkholderia multivorans (B9BCZ1), Burkholderia multivorans CGD1 (B9BCZ1), Burkholderia sp. BT03, Butyrivibrio sp. MC2021, Calidithermus chliarophilus, Cellulophaga algicola DSM 14237, Chryseobacterium sp. UNC8MFCol, Desulfatibacillum aliphaticivorans, Drepanopeziza brunnea, Drepanopeziza brunnea MB_m1, Dyadobacter alkalitolerans, Flexithrix dorotheae, Fodinicurvata sediminis, Geodermatophilus obscurus (D2SGH7), Geodermatophilus obscurus ATCC 25078 (D2SGH7), Janthinobacterium sp. Marseille (A6T0X3), Maribacter antarcticus, Maricaulis maris, Maricaulis maris MCS10, Methanosarcina mazei (Q8PXI9), Methanosarcina mazei BAA-159 (Q8PXI9), Microscilla marina (A1ZD79), Microscilla marina ATCC 23134 (A1ZD79), Morganella morganii subsp. morganii, Morganella morganii subsp. morganii KT, Niabella soli, Niabella soli DSM 19437, Nocardiopsis dassonvillei ATCC 23218 (D7B8P3), Pantoea sp. AS-PWVM4, Parabacteroides gordonii, Pedobacter jeongneungensis, Pseudomonas entomophila (Q1I7X1), Pseudomonas entomophila L48 (Q1I7X1), Pseudomonas oleovorans, Pseudomonas oleovorans CECT:5344, Pseudomonas sp. GM41, Pseudonocardia spinosispora, Rhizobium leguminosarum bv. trifolii, Rhizobium leguminosarum bv. trifolii WSM1325, Rhodococcus aetherivorans, Rubellimicrobium mesophilum, Rubellimicrobium mesophilum DSM 19309, Runella slithyformis, Saccharomyces cerevisiae (B3LU11), Saccharomyces cerevisiae RM11-1a (B3LU11), Scheffersomyces stipitis (A3LXL4), Scheffersomyces stipitis ATCC 58785 (A3LXL4), Sediminispirochaeta bajacaliforniensis, Shewanella sediminis (A8FQL4), Shewanella sediminis HAW-EB3 (A8FQL4), Sphingobacterium thalpophilum, Stappia stellulata, Streptomyces albus (D6B7V7), Streptomyces albus J1074 (D6B7V7), Synechocystis sp. PCC 6803, Thalassiosira pseudonana (B8C1M9), Thalassospira lucentensis, Tomitella biformata
Manually annotated by BRENDA team
Lehmann, T.; Janowitz, T.; Sanchez-Parra, B.; Alonso, M.P.; Trompetter, I.; Piotrowski, M.; Pollmann, S.
Arabidopsis nitrilase 1 contributes to the regulation of root growth and development through modulation of auxin biosynthesis in seedlings
Front. Plant Sci.
8
36
2017
Arabidopsis thaliana (P32961), Arabidopsis thaliana
Manually annotated by BRENDA team