Information on EC 1.14.13.118 - valine N-monooxygenase

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The expected taxonomic range for this enzyme is: Manihot esculenta

EC NUMBER
COMMENTARY hide
1.14.13.118
-
RECOMMENDED NAME
GeneOntology No.
valine N-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-valine + 2 O2 + 2 NADPH + 2 H+ = (E)-2-methylpropanal oxime + 2 NADP+ + CO2 + 3 H2O
show the reaction diagram
-
-
-
-
L-valine + O2 + NADPH + H+ = N-hydroxy-L-valine + NADP+ + H2O
show the reaction diagram
-
-
-
-
N,N-dihydroxy-L-valine = (E)-2-methylpropanal oxime + CO2 + H2O
show the reaction diagram
spontaneous
-
-
-
N-hydroxy-L-valine + O2 + NADPH + H+ = N,N-dihydroxy-L-valine + NADP+ + H2O
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cyanoamino acid metabolism
-
-
Glucosinolate biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
L-valine,NADPH:oxygen oxidoreductase (N-hydroxylating)
A heme-thiolate protein (P-450). This enzyme catalyses two successive N-hydroxylations of L-valine, the first committed steps in the biosynthesis of the cyanogenic glucoside linamarin in Manihot esculenta (cassava). The product of the two hydroxylations, N,N-dihydroxy-L-valine, is extremely labile and dehydrates spontaneously. The dehydrated product is then subject to a decarboxylation that produces the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The product, (E)-2-methylpropanal oxime, undergoes a spontaneous isomerization to the (Z) form. The enzyme can also accept L-isoleucine as substrate, with a lower activity. It is different from EC 1.14.13.117 (isoleucine N-monooxygenase), which prefers L-isoleucine.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-isoleucine + 2 O2 + 2 NADPH + 2 H+
(E)-2-methylbutanal oxime + 2 NADP+ + CO2 + 3 H2O
show the reaction diagram
L-isoleucine + O2 + NADPH + H+
(Z)-2-methylbutanal oxime + NADP+ + CO2 + H2O
show the reaction diagram
-
-
-
?
L-valine + 2 O2 + 2 NADPH + 2 H+
(E)-2-methylpropanal oxime + 2 NADP+ + CO2 + 3 H2O
show the reaction diagram
L-valine + O2 + NADPH + H+
(Z)-2-methylpropanal oxime + NADP+ + CO2 + H2O
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-isoleucine + O2 + NADPH + H+
(Z)-2-methylbutanal oxime + NADP+ + CO2 + H2O
show the reaction diagram
Q9M7B7, Q9M7B8
-
-
-
?
L-valine + O2 + NADPH + H+
(Z)-2-methylpropanal oxime + NADP+ + CO2 + H2O
show the reaction diagram
Q9M7B7, Q9M7B8
-
-
-
?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diphenyleneiodonium chloride
;
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.3
L-isoleucine
pH 7.9, 30C
2.2
L-valine
pH 7.9, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.103
L-isoleucine
Manihot esculenta
Q9M7B7, Q9M7B8
pH 7.9, 30C
0.162
L-valine
Manihot esculenta
Q9M7B7, Q9M7B8
pH 7.9, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
L-isoleucine
Manihot esculenta
Q9M7B7, Q9M7B8
pH 7.9, 30C
311
0.074
L-valine
Manihot esculenta
Q9M7B7, Q9M7B8
pH 7.9, 30C
246
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.9
assay at; assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
assay at; assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 62000, SDS-PAGE and calculated
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
glycosylation of the asparagine residues at the N-terminus
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme, reconstitution in lipid micelles; recombinant enzyme, reconstitution in lipid micelles
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Arabidopsis thaliana
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expression in Lotus japonicus
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expression in Pichia pastoris; expression in Pichia pastoris
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
expression of CYP79D2 from cassava in Arabidopsis thaliana results in the production of valine- and isoleucine-derived glucosinolates not normally found in this ecotype. The transgenic lines show no morphological phenotype, and the level of endogenous glucosinolates is not affected. The novel glucosinolates constitute up to 35% of the total glucosinolate content in mature rosette leaves and up to 48% in old leaves. At increased concentrations of these glucosinolates, the proportion of Val-derived glucosinolates decreases. As the isothiocyanates produced from the Val- and isoleucine-derived glucosinolates are volatile, metabolically engineered plants producing these glucosinolates have acquired novel properties with great potential for improvement of resistance to herbivorous insects and for biofumigation
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
-
expression of CYP79D2 from cassava in Arabidopsis thaliana results in the production of valine- and isoleucine-derived glucosinolates not normally found in this ecotype. The transgenic lines show no morphological phenotype, and the level of endogenous glucosinolates is not affected. The novel glucosinolates constitute up to 35% of the total glucosinolate content in mature rosette leaves and up to 48% in old leaves. At increased concentrations of these glucosinolates, the proportion of Val-derived glucosinolates decreases. As the isothiocyanates produced from the Val- and isoleucine-derived glucosinolates are volatile, metabolically engineered plants producing these glucosinolates have acquired novel properties with great potential for improvement of resistance to herbivorous insects and for biofumigation