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Information on EC 3.5.5.4 - cyanoalanine nitrilase
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3.5.5.4 cyanoalanine nitrilaseIUBMB Comments
L-Asparagine is formed as an intermediate. cf. EC 4.2.1.65, 3-cyanoalanine hydratase and EC 3.5.1.1, asparaginase.
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Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
nitrilase 4, cyanoalanine hydratase, nit4a, nit4b, nit4b2, beta-cyanoalanine nitrilase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
beta-cyanoalanine nitrilase
beta-cyanoalanine synthase
Nit4
NIT4-1
NIT4-2
NIT4A
NIT4B
nitrilase 4
PinA
beta-cyanoalanine nitrilase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3-cyano-L-alanine + 2 H2O = L-aspartate + NH3
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of nitriles
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
3-cyano-L-alanine aminohydrolase
L-Asparagine is formed as an intermediate. cf. EC 4.2.1.65, 3-cyanoalanine hydratase and EC 3.5.1.1, asparaginase.
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CAS REGISTRY NUMBER
COMMENTARY
85638-44-4
-
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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
phenyl-3-propionitrile + H2O
phenyl-3-propionic acid + NH3
-
-
-
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
enzyme has additional hydratase activity for 3-cyano-L-alanine, ratio of hydratase activity to nitrilase activity is 3.3:1. L-asparagine and L-aspartate are formed at the same time, asparagine is not an intermediate
-
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
enzyme has additional hydratase activity for 3-cyano-L-alanine, ratio of hydratase activity to nitrilase activity is 4:1. L-asparagine and L-aspartate are formed at the same time, asparagine is not an intermediate
-
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
-
L-asparagine is formed as an intermediate
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
-
L-asparagine is formed as an intermediate
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
high activity substrate for isozyme complexes NIT4A/B2 and NIT4A/B1
-
-
ir
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
the reaction is catalyzed only by isoform NIT4A, L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
the reaction is catalyzed only by isoform NIT4A, L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
beta-cyano-L-alanine + H2O
L-aspartate + NH3
-
L-asparagine is formed as an intermediate
-
-
?
additional information
?
-
-
indole-3-acetonitrile is no substrate for NIT-T4
-
-
-
additional information
?
-
-
isoform NIT4B does not show beta-cyano-L-alanine-hydrolyzing activity
-
-
-
additional information
?
-
no substrate: indole-3-acetonitrile
-
-
-
additional information
?
-
no substrate: indole-3-acetonitrile
-
-
-
additional information
?
-
-
no substrates are various nitrile or amide compounds, overview
-
-
-
additional information
?
-
-
no substrates are various nitrile or amide compounds, overview
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-
-
additional information
?
-
-
recombinant NIT4 isozymes NIT4A, NIT4B1, and NIT4B2 do not hydrolyze 3-cyano-L-alanine, benzonitrile, 4-hydroxybenzonitrile, butyronitrile, and 4-pentenenitrile
-
-
-
additional information
?
-
-
isoform NIT4B1 does not show any beta-cyano-L-alanine-hydrolyzing activity
-
-
-
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NATURAL SUBSTRATE
NATURAL 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
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
-
L-asparagine is formed as an intermediate
?
3-cyano-L-alanine + H2O
L-aspartate + NH3
-
-
L-asparagine is formed as an intermediate
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.69
3-Cyano-L-alanine
-
in 50 mM sodium phosphate (pH 8.0) containing 0.2% (w/v) BSA with 5 mM substrate, at 35°C
0.86
3-Cyano-L-alanine
-
isozyme complex NIT4A/B1, in 50 mM potassium phosphate (pH 8.0), 1 mM dithiothreitol, at 37°C
0.89
3-Cyano-L-alanine
-
isozyme complex NIT4A/B2, in 50 mM potassium phosphate (pH 8.0), 1 mM dithiothreitol, at 37°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
19.4
3-Cyano-L-alanine
-
in 50 mM sodium phosphate (pH 8.0) containing 0.2% (w/v) BSA with 5 mM substrate, at 35°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
143.7
substrate 3-cyano-L-alanine, pH 8.0, 37°C; substrate 3-cyano-L-alanine, pH 8.0, 37°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoform LaNIT4A, in addition to nitrilase activity, enzyme shows cyanoalanine hydratase activity
SwissProt
brenda
isoform LaNIT4B, in addition to nitrilase activity, enzyme shows cyanoalanine hydratase activity
SwissProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
the NIT4 deletion shows decreased growth along with altered chlorophyll content under water deficit as compared to the wild type
physiological function
-
increased expression of beta-cyanoalanine nitrilase improves cyanide tolerance in Arabidopsis thaliana
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
A0A212IW40_9DELT
315
0
34524
TrEMBL
A0A0B6AAE0_BACMB
Bacillus megaterium (strain ATCC 14581 / DSM 32 / JCM 2506 / NBRC 15308 / NCIMB 9376 / NCTC 10342 / VKM B-512)
318
0
35116
TrEMBL
A0A212KM05_9PROT
311
0
33250
TrEMBL
K0KKW9_WICCF
Wickerhamomyces ciferrii (strain F-60-10 / ATCC 14091 / CBS 111 / JCM 3599 / NBRC 0793 / NRRL Y-1031)
304
0
33351
TrEMBL
F0Q9A2_ACIAP
Acidovorax avenae (strain ATCC 19860 / DSM 7227 / JCM 20985 / NCPPB 1011)
316
0
33638
TrEMBL
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
polymer
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CRYSTALLIZATION/commentary
ORGANISM
UNIPROT
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
PinA is able to complement a nit4 mutation in Arabidopsis thaliana. Overexpression of PinA in wild-type Arabidopsis thaliana results in increased growth in high concentrations of 3-cyano-L-alanine and in increased root elongation in the absence of exogenous 3-cyano-L-alanine
additional information
-
PinA is able to complement a nit4 mutation in Arabidopsis thaliana. Overexpression of PinA in wild-type Arabidopsis thaliana results in increased growth in high concentrations of 3-cyano-L-alanine and in increased root elongation in the absence of exogenous 3-cyano-L-alanine
-
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION/commentary
ORGANISM
UNIPROT
LITERATURE
Ni-Sepharose Fast Flow column chromatography and Sephadex G-15 gel filtration
-
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CLONED/commentary
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
degradation
degradation
-
this enzyme is of interest for the use in the biodegradation of cyanide and the degradation of nitrile wastes
degradation
-
this enzyme is of interest for the use in the biodegradation of cyanide and the degradation of nitrile wastes
degradation
-
this enzyme is of interest for the use in the biodegradation of cyanide and the degradation of nitrile wastes
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yanase, H.; Sakai, T.; Tonomura, K.
Metabolism of nitriles in microorganisms. Part V. Purification, crystallization and some properties of beta-cyano-L-alanine-degrading enzyme in Pseudomonas sp. 13
Agric. Biol. Chem.
47
473-482
1983
Pseudomonas sp., Pseudomonas sp. 13
-
brenda
Piotrowski, M.; Volmer, J.J.
Cyanide metabolism in higher plants: cyanoalanine hydratase is a NIT4 homolog
Plant Mol. Biol.
61
111-122
2006
Lupinus angustifolius (Q3LRV4), Lupinus angustifolius (Q5QGZ8)
brenda
Kriechbaumer, V.; Park, W.J.; Piotrowski, M.; Meeley, R.B.; Gierl, A.; Glawischnig, E.
Maize nitrilases have a dual role in auxin homeostasis and beta-cyanoalanine hydrolysis
J. Exp. Bot.
58
4225-4233
2007
Zea mays
brenda
Ishikawa, T.; Okazaki, K.; Kuroda, H.; Itoh, K.; Mitsui, T.; Hori, H.
Molecular cloning of Brassica rapa nitrilases and their expression during clubroot development
Mol. Plant Pathol.
8
623-637
2007
Brassica rapa
brenda
Jenrich, R.; Trompetter, I.; Bak, S.; Olsen, C.E.; Moller, B.L.; Piotrowski, M.
Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism
Proc. Natl. Acad. Sci. USA
104
18848-18853
2007
Sorghum bicolor
brenda
Howden, A.J.; Harrison, C.J.; Preston, G.M.
A conserved mechanism for nitrile metabolism in bacteria and plants
Plant J.
57
243-253
2009
Pseudomonas fluorescens, Pseudomonas fluorescens SBW25
brenda
Gupta, N.; Balomajumder, C.; Agarwal, V.
Enzymatic mechanism and biochemistry for cyanide degradation: A review
J. Hazard. Mater.
176
1-13
2010
Bacillus megaterium, Chromobacterium violaceum, Escherichia coli
brenda
Janowitz, T.; Trompetter, I.; Piotrowski, M.
Evolution of nitrilases in glucosinolate-containing plants
Phytochemistry
70
1680-1686
2009
Allium cepa, Arabidopsis thaliana, Brassica rapa, Capsella rubella, Carica papaya, Curcuma longa, Glycine max, Hordeum vulgare, Lactuca sativa, Linum usitatissimum, Lotus japonicus, Lupinus angustifolius, Manihot esculenta, Medicago truncatula, Mesembryanthemum crystallinum, Nicotiana tabacum, Oryza sativa, Physcomitrella patens, Pinus taeda, Populus trichocarpa, Ricinus communis, Saccharum officinarum, Selaginella moellendorffii, Solanum lycopersicum, Sorghum bicolor, Tarenaya spinosa, Triticum aestivum, Tropaeolum majus, Vitis vinifera, Zea mays
brenda
O'Leary, B.; Preston, G.M.; Sweetlove, L.J.
Increased beta-cyanoalanine nitrilase activity improves cyanide tolerance and assimilation in Arabidopsis
Mol. Plant
7
231-243
2014
Pseudomonas fluorescens
brenda
Machingura, M.; Sidibe, A.; Wood, A.J.; Ebbs, S.D.
The beta-cyanoalanine pathway is involved in the response to water deficit in Arabidopsis thaliana
Plant Physiol. Biochem.
63
159-169
2013
Arabidopsis thaliana
brenda
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