Information on EC 1.14.14.41 - (E)-2-methylbutanal oxime monooxygenase

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The expected taxonomic range for this enzyme is: Manihot esculenta

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EC NUMBER
COMMENTARY hide
1.14.14.41
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RECOMMENDED NAME
GeneOntology No.
(E)-2-methylbutanal oxime monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-2-methylbutanal oxime + [reduced NADPH-hemoprotein reductase] + O2 = 2-hydroxy-2-methylbutanenitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(1) overall reaction
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(E)-2-methylbutanal oxime = (Z)-2-methylbutanal oxime
show the reaction diagram
(1a)
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(E)-2-methylpropanal oxime + [reduced NADPH-hemoprotein reductase] + O2 = 2-hydroxy-2-methylpropanenitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(2) overall reaction
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(E)-2-methylpropanal oxime = (Z)-2-methylpropanal oxime
show the reaction diagram
(2a)
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(Z)-2-methylbutanal oxime = 2-methylbutanenitrile + H2O
show the reaction diagram
(1b)
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(Z)-2-methylpropanal oxime = 2-methylpropanenitrile + H2O
show the reaction diagram
(2b)
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2-methylbutanenitrile + [reduced NADPH-hemoprotein reductase] + O2 = 2-hydroxy-2-methylbutanenitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1c)
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2-methylpropanenitrile + [reduced NADPH-hemoprotein reductase] + O2 = 2-hydroxy-2-methylpropanenitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
catalytic reaction mechanism, detailed overview
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cyanoamino acid metabolism
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(E)-2-methylbutanal oxime,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucosides lotaustralin and linamarin. It catalyses three different activities - isomerization of its substrate, the (E) isomer, to the (Z) isomer, dehydration, and C-hydroxylation.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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CYP71E7 is the oxime-metabolizing cytochrome P450 in the biosynthesis of lotaustralin and linamarin. Expression of CYP71E7 in yeast affords microsomes converting 2-methylpropanal oxime and 2-methylbutanal oxime to the corresponding cyanohydrins, which dissociate into acetone and 2-butanone, respectively, and hydrogen cyanide
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-2-methylbutanal oxime
(Z)-2-methylbutanal oxime
show the reaction diagram
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?
(E)-2-methylbutanal oxime + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxy-2-methylbutanenitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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i.e. isoleucine-derived oxime
overall reaction
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?
(E)-2-methylpropanal oxime
(Z)-2-methylpropanal oxime
show the reaction diagram
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-
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?
(E)-2-methylpropanal oxime + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxy-2-methylpropanenitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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i.e. valine-derived oxime
overall reaction
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(Z)-2-methylbutanal oxime
2-methylbutanenitrile + H2O
show the reaction diagram
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?
(Z)-2-methylpropanal oxime
2-methylpropanenitrile + H2O
show the reaction diagram
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?
2-methylbutanenitrile + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxy-2-methylbutanenitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
2-methylpropanenitrile + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxy-2-methylpropanenitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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N-hydroxy-2-(4-hydroxypheny)-lethanimine + [reduced NADPH-hemoprotein reductase] + O2
(4-hydroxyphenyl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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i.e. phenylalanine-derived oxime
overall reaction
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N-hydroxy-2-phenylethanimine + [reduced NADPH-hemoprotein reductase] + O2
phenylacetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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i.e. phenylalanine-derived oxime
overall reaction
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additional information
?
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CYP71E7 exhibits low specificity for the side chain of the substrate and catalyzes the conversion of aliphatic and aromatic oximes
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
n-octylamine
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competitive
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.021
(E)-2-methylbutanal oxime
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pH 7.9, 28°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.28
(E)-2-methylbutanal oxime
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pH 7.9, 28°C
0.35
(E)-2-methylpropanal oxime
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pH 7.9, 28°C
0.13
N-hydroxy-2-(4-hydroxypheny)-lethanimine
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pH 7.9, 28°C
0.02
N-hydroxy-2-phenylethanimine
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pH 7.9, 28°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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of nearly unfolded leaf
Manually annotated by BRENDA team
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uridine diphosphate glycosyltransferases UGT85K4 and UGT85K5 are co-expressed with CYP79D1 and CYP71E7 paralogs, which catalyze earlier steps in cyanogenic glucoside synthesis, in the cortex, xylem and phloem parenchyma, and in specific cells in the endodermis of the petiole of the first unfolded leaf
Manually annotated by BRENDA team
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uridine diphosphate glycosyltransferases UGT85K4 and UGT85K5 are co-expressed with CYP79D1 and CYP71E7 paralogs, which catalyze earlier steps in cyanogenic glucoside synthesis, in the cortex, xylem and phloem parenchyma, and in specific cells in the endodermis of the petiole of the first unfolded leaf
Manually annotated by BRENDA team
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.14.41)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)