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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
an L-polyhomomethionine
+
2
+
2
=
+
2
+
+
3
Synonyms
cyp79f1, cyp79f2, dihomomethionine n-hydroxylase,
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dihomomethionine N-hydroxylase
-
hexahomomethionine N-hydroxylase
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CYP79F1
-
-
-
CYP79F2
-
-
-
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an L-N,N-dihydroxypolyhomomethionine = an (E)-omega-(methylsulfanyl)alkanal oxime + CO2 + H2O
(1c)
-
-
an L-N-hydroxypolyhomomethionine + [reduced NADPH-hemoprotein reductase] + O2 = an L-N,N-dihydroxypolyhomomethionine + [oxidized NADPH-hemoprotein reductase] + H2O
(1b)
-
-
an L-polyhomomethionine + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = an (E)-omega-(methylsulfanyl)alkanal oxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
overall reaction
-
-
an L-polyhomomethionine + [reduced NADPH-hemoprotein reductase] + O2 = an L-N-hydroxypolyhomomethionine + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
-
-
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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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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
?
-
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 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 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
-
?
additional information
?
-
isoform CYP79F2 exclusively metabolizes long-chain elongated penta- and hexahomomethionines. 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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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
?
-
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 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 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
-
-
?
additional information
?
-
isoform CYP79F2 exclusively metabolizes long-chain elongated penta- and hexahomomethionines. 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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0.034
L-dihomomethionine
pH 7.5, 25°C
0.026 - 0.074
L-hexahomomethionine
0.216 - 0.374
L-pentahomomethionine
0.194
L-tetrahomomethionine
pH 7.5, 25°C
0.037
L-trihomomethionine
pH 7.5, 25°C
0.026
L-hexahomomethionine
pH 7.5, 25°C
0.074
L-hexahomomethionine
pH 7.5, 25°C
0.216
L-pentahomomethionine
pH 7.5, 25°C
0.374
L-pentahomomethionine
pH 7.5, 25°C
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
brenda
strongly expressed in hypocotyl and root
brenda
strongly expressed in hypocotyl and root
brenda
strongly expressed in cotyledons, rosette leaves, stems, and siliques
brenda
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
brenda
strongly expressed in cotyledons, rosette leaves, stems, and siliques
brenda
expression throughout leaf development with lower transcript levels during the younger stages
brenda
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
brenda
strongly expressed in cotyledons, rosette leaves, stems, and siliques
brenda
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
brenda
strongly expressed in cotyledons, rosette leaves, stems, and siliques
brenda
the transcript levels are higher in cotyledon, leaf and stem compared with flower and silique
brenda
additional information
CYP79F1 shows high expression at reproductive phase and significantly high in genotypes with high glucoraphanin content
brenda
additional information
-
CYP79F1 shows high expression at reproductive phase and significantly high in genotypes with high glucoraphanin content
brenda
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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
physiological function
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
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
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C79F1_ARATH
538
2
61695
Swiss-Prot
Secretory Pathway (Reliability: 1 )
C79F2_ARATH
537
1
61432
Swiss-Prot
Secretory Pathway (Reliability: 1 )
A0A0B5GAE0_BRAOA
541
0
61503
TrEMBL
-
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61000
x * 61000, calculated
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?
x * 62000, calculated and SDS-PAGE
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modeling of structure, CYP79F1 contains a transmembrane domain at residues 13-35 and has two possible transmembrane helices
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expression in Escherichia coli
expression in Saccharomyces cerevisiae
expression in Escherichia coli
expression in Escherichia coli
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Hansen, C.H.; Wittstock, U.; Olsen, C.E.; Hick, A.J.; Pickett, J.A.; Halkier, B.A.
Cytochrome p450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates
J. Biol. Chem.
276
11078-11085
2001
Arabidopsis thaliana (Q949U1), Arabidopsis thaliana
brenda
Yin, L.; Chen, C.; Chen, G.; Cao, B.; Lei, J.
Molecular cloning, expression pattern and genotypic effects on glucoraphanin biosynthetic related genes in Chinese kale (Brassica oleracea var. alboglabra Bailey)
Molecules
20
20254-20267
2015
Brassica oleracea var. alboglabra (A0A0B5GAE0), Brassica oleracea var. alboglabra
brenda
Chen, S.; Glawischnig, E.; Jörgensen, K.; Naur, P.; Jörgensen, B.; Olsen, C.E.; Hansen, C.H.; Rasmussen, H.; Pickett, J.A.; Halkier, B.A.
CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis
Plant J.
33
923-937
2003
Arabidopsis thaliana (Q949U1), Arabidopsis thaliana (Q9FUY7), Arabidopsis thaliana
brenda
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1.14.14.42 homomethionine N-monooxygenase
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