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Enzyme Nomenclature
Information on EC 1.14.14.42 - homomethionine N-monooxygenase
for references in articles please use BRENDA:EC1.14.14.42
Word Map on EC 1.14.14.42
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.14.42
-
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RECOMMENDED NAME
GeneOntology No.
homomethionine N-monooxygenase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-isoleucine + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (1E,2S)-2-methylbutanal oxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
overall reaction
-
-
-
L-isoleucine + [reduced NADPH-hemoprotein reductase] + O2 = N-hydroxy-L-isoleucine + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
-
-
-
N,N-dihydroxy-L-isoleucine = (1E,2S)-2-methylbutanal oxime + CO2 + H2O
(1c)
-
-
-
N-hydroxy-L-isoleucine + [reduced NADPH-hemoprotein reductase] + O2 = N,N-dihydroxy-L-isoleucine + [oxidized NADPH-hemoprotein reductase] + H2O
(1b)
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
L-homomethionine,[NADPH-hemoprotein reductase]:oxygen oxidoreductase
This plant cytochrome P-450 (heme thiolate) enzyme is involved in methionine-derived aliphatic glucosinolates biosynthesis. It catalyses two successive N-hydroxylations, which are followed by dehydration and decarboxylation. CYP79F1 from Arabidopsis thaliana can metabolize mono-, di-, tri-, tetra-, penta-, and hexahomomethionine to their corresponding aldoximes, while CYP79F2 from the same plant can only metabolize penta- and hexahomomethionine.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
transgenic Arabidopsis thaliana with cosuppression of CYP79F1 have a reduced content of aliphatic glucosinolates and a highly increased level of dihomomethionine and trihomomethionine. The transgenic plants have a morphological phenotype showing loss of apical dominance and formation of multiple axillary shoots
physiological function
a transposon-tagged CYP79F1 knockout mutant completely lacks short-chain aliphatic glucosinolates, but has an increased level of long-chain aliphatic glucosinolates, especially in leaves and seeds; the level of long-chain aliphatic glucosinolates in a transposon-tagged CYP79F2 knockout mutant is substantially reduced, whereas the level of short-chain aliphatic glucosinolates is not affected
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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
L-dihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiopentanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
-
-
?
L-dihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
omega-(methylthio)-(E)-pentanaldehyde oxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction, product is the precursor of the major glucosinolates in leaves of Arabidopsis thaliana
-
?
L-hexahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiononanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction
-
?
L-homomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiobutanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
-
-
?
L-pentahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiooctanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction
-
?
L-tetrahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthioheptanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction
-
?
L-trihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiohexanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction
-
?
L-trihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
omega-(methylthio)-(E)-hexanaldehyde oxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
-
overall reaction
-
?
additional information
?
-
isoform CYP79F1 metabolizes mono- to hexahomomethionine, resulting in both short- and long-chain aliphatic glucosinolates. No substrates: phenylalanine,homophenylalanine, tyrosine, tryptophan, and methionine
-
-
-
additional information
?
-
isoform CYP79F2 exclusively metabolizes long-chain elongated penta- and hexahomomethionines. No substrates: phenylalanine, homophenylalanine, tyrosine, tryptophan, and methionine
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
L-dihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiopentanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
-
-
?
L-dihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
omega-(methylthio)-(E)-pentanaldehyde oxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q949U1
-
overall reaction, product is the precursor of the major glucosinolates in leaves of Arabidopsis thaliana
-
?
L-hexahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiononanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
overall reaction
-
?
L-homomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiobutanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
-
-
?
L-pentahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiooctanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
overall reaction
-
?
L-tetrahomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthioheptanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
overall reaction
-
?
L-trihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
4-methylthiohexanaldoxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q9FUY7
-
overall reaction
-
?
L-trihomomethionine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
omega-(methylthio)-(E)-hexanaldehyde oxime + CO2 + 3 H2O + 2 [oxidized NADPH-hemoprotein reductase]
Q949U1
-
overall reaction
-
?
additional information
?
-
Q9FUY7
isoform CYP79F1 metabolizes mono- to hexahomomethionine, resulting in both short- and long-chain aliphatic glucosinolates. No substrates: phenylalanine,homophenylalanine, tyrosine, tryptophan, and methionine
-
-
-
additional information
?
-
Q9FUY7
isoform CYP79F2 exclusively metabolizes long-chain elongated penta- and hexahomomethionines. No substrates: phenylalanine, homophenylalanine, tyrosine, tryptophan, and methionine
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
additional information
strongly expressed in cotyledons, rosette leaves, stems, and siliques
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
strongly expressed in cotyledons, rosette leaves, stems, and siliques
expression throughout leaf development with lower transcript levels during the younger stages; the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
strongly expressed in cotyledons, rosette leaves, stems, and siliques
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
strongly expressed in cotyledons, rosette leaves, stems, and siliques
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
additional information
CYP79F1 shows high expression at reproductive phase and significantly high in genotypes with high glucoraphanin content
additional information
-
CYP79F1 shows high expression at reproductive phase and significantly high in genotypes with high glucoraphanin content
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of structure, CYP79F1 contains a transmembrane domain at residues 13-35 and has two possible transmembrane helices
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli; expression in Saccharomyces cerevisiae
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.14.42)
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