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Information on EC 1.14.13.237 - aliphatic glucosinolate S-oxygenase
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1.14.13.237 aliphatic glucosinolate S-oxygenaseIUBMB Comments
The enzyme is a member of the flavin-dependent monooxygenase (FMO) family (cf. EC 1.14.13.8). The plant Arabidopsis thaliana contains five isoforms. GS-OX1 through GS-OX4 are able to catalyse the S-oxygenation independent of chain length, while GS-OX5 is specific for 8-(methylsulfanyl)octyl glucosinolate.
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Word Map
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
fmogs-ox, flavin-containing monooxygenase 2, fmogs-ox2, fmogs-ox1, flavin-containing monooxygenase 4, fmo gs-ox1, fmogs-ox4, gs-ox1, fmogs-ox5, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
flavin-containing monooxygenase 2
flavin-containing monooxygenase 4
FMO2
FMO4
FMOGS-OX
FMOGS-OX1
FMOGS-OX2
FMOGS-OX3
FMOGS-OX4
FMOGS-OX5
GS-OX1
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-
-
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omega-(methylthio)alkylglucosinolate S-oxygenase
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-
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2 = an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
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PATHWAY SOURCE
PATHWAYS
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, , , , ,
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SYSTEMATIC NAME
IUBMB Comments
omega-(methylthio)alkyl-glucosinolate,NADPH:oxygen S-oxidoreductase
The enzyme is a member of the flavin-dependent monooxygenase (FMO) family (cf. EC 1.14.13.8). The plant Arabidopsis thaliana contains five isoforms. GS-OX1 through GS-OX4 are able to catalyse the S-oxygenation independent of chain length, while GS-OX5 is specific for 8-(methylsulfanyl)octyl glucosinolate.
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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
3-methylthiopropyl-glucosinolate + NADPH + H+ + O2
3-methylsulfinylpropyl-glucosinolate + NADP+ + H2O
4-methylthiobutyl-glucosinolate + NADPH + H+ + O2
4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
5-methylthiopentyl-glucosinolate + NADPH + H+ + O2
5-methylsulfinylpentyl-glucosinolate + NADP+ + H2O
6-methylthiohexyl-glucosinolate + NADPH + H+ + O2
6-methylsulfinylhexyl-glucosinolate + NADP+ + H2O
7-methylthioheptyl-glucosinolate + NADPH + H+ + O2
7-methylsulfinylheptyl-glucosinolate + NADP+ + H2O
8-methylthiooctyl-glucosinolate + NADPH + H+ + O2
8-methylsulfinyloctyl-glucosinolate + NADP+ + H2O
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
desulfo-4-methylsulfinylbutyl-glucosinolate + NADPH + H+ + O2
desulfo-4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
glucoerucin + NADPH + H+ + O2
glucoraphanin + NADP+ + H2O
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-
-
?
additional information
?
-
no activity with methionine, dihomomethionine and 5-methylthiopentaldoxime
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-
?
3-methylthiopropyl-glucosinolate + NADPH + H+ + O2
3-methylsulfinylpropyl-glucosinolate + NADP+ + H2O
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-
-
-
?
3-methylthiopropyl-glucosinolate + NADPH + H+ + O2
3-methylsulfinylpropyl-glucosinolate + NADP+ + H2O
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-
-
?
3-methylthiopropyl-glucosinolate + NADPH + H+ + O2
3-methylsulfinylpropyl-glucosinolate + NADP+ + H2O
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-
-
?
4-methylthiobutyl-glucosinolate + NADPH + H+ + O2
4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
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-
-
-
?
4-methylthiobutyl-glucosinolate + NADPH + H+ + O2
4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
-
-
-
?
4-methylthiobutyl-glucosinolate + NADPH + H+ + O2
4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
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-
-
?
5-methylthiopentyl-glucosinolate + NADPH + H+ + O2
5-methylsulfinylpentyl-glucosinolate + NADP+ + H2O
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-
-
-
?
5-methylthiopentyl-glucosinolate + NADPH + H+ + O2
5-methylsulfinylpentyl-glucosinolate + NADP+ + H2O
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-
-
?
5-methylthiopentyl-glucosinolate + NADPH + H+ + O2
5-methylsulfinylpentyl-glucosinolate + NADP+ + H2O
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-
-
?
6-methylthiohexyl-glucosinolate + NADPH + H+ + O2
6-methylsulfinylhexyl-glucosinolate + NADP+ + H2O
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-
-
-
?
6-methylthiohexyl-glucosinolate + NADPH + H+ + O2
6-methylsulfinylhexyl-glucosinolate + NADP+ + H2O
-
-
-
?
6-methylthiohexyl-glucosinolate + NADPH + H+ + O2
6-methylsulfinylhexyl-glucosinolate + NADP+ + H2O
-
-
-
?
7-methylthioheptyl-glucosinolate + NADPH + H+ + O2
7-methylsulfinylheptyl-glucosinolate + NADP+ + H2O
-
-
-
-
?
7-methylthioheptyl-glucosinolate + NADPH + H+ + O2
7-methylsulfinylheptyl-glucosinolate + NADP+ + H2O
-
-
-
?
7-methylthioheptyl-glucosinolate + NADPH + H+ + O2
7-methylsulfinylheptyl-glucosinolate + NADP+ + H2O
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-
-
?
8-methylthiooctyl-glucosinolate + NADPH + H+ + O2
8-methylsulfinyloctyl-glucosinolate + NADP+ + H2O
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-
-
-
?
8-methylthiooctyl-glucosinolate + NADPH + H+ + O2
8-methylsulfinyloctyl-glucosinolate + NADP+ + H2O
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-
-
?
8-methylthiooctyl-glucosinolate + NADPH + H+ + O2
8-methylsulfinyloctyl-glucosinolate + NADP+ + H2O
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-
-
?
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
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-
-
?
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
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-
-
?
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
-
-
-
-
?
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
-
-
-
?
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
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-
-
?
desulfo-4-methylsulfinylbutyl-glucosinolate + NADPH + H+ + O2
desulfo-4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
-
-
-
-
?
desulfo-4-methylsulfinylbutyl-glucosinolate + NADPH + H+ + O2
desulfo-4-methylsulfinylbutyl-glucosinolate + NADP+ + H2O
-
-
-
?
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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
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
glucoerucin + NADPH + H+ + O2
glucoraphanin + NADP+ + H2O
-
-
-
?
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
-
-
-
?
an omega-(methylsulfanyl)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
-
-
-
?
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
-
-
-
-
?
an omega-(methylthio)alkyl-glucosinolate + NADPH + H+ + O2
an omega-(methylsulfinyl)alkyl-glucosinolate + NADP+ + H2O
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-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Prader-Willi Syndrome
Trimethylaminuria in a girl with Prader-Willi syndrome and del(15)(q11q13).
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
quantitative RT-PCR enzyme expression analysis in leaves and roots, overview
brenda
additional information
quantitative RT-PCR enzyme expression analysis in leaves and roots, overview
brenda
additional information
-
quantitative RT-PCR enzyme expression analysis in leaves and roots, overview
brenda
additional information
-
quantitative RT-PCR enzyme expression analysis in leaves and roots, overview
-
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
in wild-type plants, glucose treatment drastically reduces the accumulation of 4-methylthiobutyl glucosinolate, which is not observed in the FMOGS-Ox2 mutant
physiological function
the first step in side-chain modification of aliphatic GSLs is the S-oxygenation of the methylthioalkyl (MT) moiety to the methylsulfinylalkyl (MS) moiety. This reaction is catalyzed by flavin-containing monooxygenase (FMOGS-OX), which is encoded by seven genes in Arabidopsis thaliana
physiological function
-
the first step in side-chain modification of aliphatic GSLs is the S-oxygenation of the methylthioalkyl (MT) moiety to the methylsulfinylalkyl (MS) moiety. This reaction is catalyzed by flavin-containing monooxygenase (FMOGS-OX), which is encoded by seven genes in Arabidopsis thaliana
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physiological function
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in wild-type plants, glucose treatment drastically reduces the accumulation of 4-methylthiobutyl glucosinolate, which is not observed in the FMOGS-Ox2 mutant
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). GSOX1_ARATH
459
0
52309
Swiss-Prot
other Location (Reliability: 5)
GSOX2_ARATH
457
0
52103
Swiss-Prot
Secretory Pathway (Reliability: 5)
GSOX3_ARATH
462
0
52688
Swiss-Prot
Chloroplast (Reliability: 5)
GSOX4_ARATH
461
0
52459
Swiss-Prot
Chloroplast (Reliability: 5)
GSOX5_ARATH
459
0
52104
Swiss-Prot
Mitochondrion (Reliability: 4)
A0A1P7ZDJ6_BRAOT
461
0
51759
TrEMBL
-
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Top10 cells
gene FMOGS-OX2, quantitative real-time PCR enzyme expression analysis
gene FMOGS-OX4, quantitative real-time PCR enzyme expression analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is increased under jasmonic acid treatment (0.1 mM)
expression of isoforms FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of transcription factors MYB28/29 and MYC2/3/4. Glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 is partially regulated by abscisic acid through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5
isoforms FMOGS-OX1, FMOGS-OX2, FMOGS-OX6, and MYB28 show upregulation (5fold) toward absisic acid, isoforms FMOGS-OX5, FMOGS-OX6, and FMOGS-OX7 toward 20 mM 20 mM 1-aminocyclopropane-1-carboxylic acid, isoform FMOGS-OX1 toward 0.05 mM methyl jasmonate, isoform FMOGS-OX7 toward 0.2 mM salicylic acid, and isoforms FMOGS-OX2 and FMOGS-OX5 toward 0.1 mM iodoacetic acid
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the expression of FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of MYB28/29 and MYC2/3/4, the transcription factors that positively regulate aliphatic GSL biosynthesis. Glucose treatment of the abscisic acid (ABA)-related mutants indicated that glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 was partially regulated by ABA through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5. In wild-type plants, glucose treatment drastically reduces the accumulation of 4-methylthiobutyl (4MT) GSL, whereas a decrease in 4MT GSL is not observed in the fmogs-ox2, abi1-1, abi2-1, aba2-1, or aba3-1 mutants. This result indicates that the decreased accumulation of 4MT GSL by glucose treatment is attributed to upregulation of FMOGS-OX2 via the ABA signaling pathway. The expression of the FMOGS-OX2 and FMOGS-OX4 genes is induced by glucose treatment independent of the MYB and MYC transcription factors
expression of isoforms FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of transcription factors MYB28/29 and MYC2/3/4. Glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 is partially regulated by abscisic acid through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5
expression of isoforms FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of transcription factors MYB28/29 and MYC2/3/4. Glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 is partially regulated by abscisic acid through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5
-
-
the expression of FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of MYB28/29 and MYC2/3/4, the transcription factors that positively regulate aliphatic GSL biosynthesis. Glucose treatment of the abscisic acid (ABA)-related mutants indicated that glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 was partially regulated by ABA through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5. In wild-type plants, glucose treatment drastically reduces the accumulation of 4-methylthiobutyl (4MT) GSL, whereas a decrease in 4MT GSL is not observed in the fmogs-ox2, abi1-1, abi2-1, aba2-1, or aba3-1 mutants. This result indicates that the decreased accumulation of 4MT GSL by glucose treatment is attributed to upregulation of FMOGS-OX2 via the ABA signaling pathway. The expression of the FMOGS-OX2 and FMOGS-OX4 genes is induced by glucose treatment independent of the MYB and MYC transcription factors
the expression of FMOGS-OX2 and FMOGS-OX4 is induced by glucose treatment, independent of MYB28/29 and MYC2/3/4, the transcription factors that positively regulate aliphatic GSL biosynthesis. Glucose treatment of the abscisic acid (ABA)-related mutants indicated that glucose-triggered upregulation of FMOGS-OX2 and FMOGS-OX4 was partially regulated by ABA through the key negative regulators ABI1 and ABI2, and the positive regulator SnRK2, but not via the transcription factor ABI5. In wild-type plants, glucose treatment drastically reduces the accumulation of 4-methylthiobutyl (4MT) GSL, whereas a decrease in 4MT GSL is not observed in the fmogs-ox2, abi1-1, abi2-1, aba2-1, or aba3-1 mutants. This result indicates that the decreased accumulation of 4MT GSL by glucose treatment is attributed to upregulation of FMOGS-OX2 via the ABA signaling pathway. The expression of the FMOGS-OX2 and FMOGS-OX4 genes is induced by glucose treatment independent of the MYB and MYC transcription factors
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kong, W.; Li, J.; Yu, Q.; Cang, W.; Xu, R.; Wang, Y.; Ji, W.
Two novel flavin-containing monooxygenases involved in biosynthesis of aliphatic glucosinolates
Front. Plant Sci.
7
1292
2016
Arabidopsis thaliana
brenda
Li, J.; Kristiansen, K.A.; Hansen, B.G.; Halkier, B.A.
Cellular and subcellular localization of flavin-monooxygenases involved in glucosinolate biosynthesis
J. Exp. Bot.
62
1337-1346
2011
Arabidopsis thaliana (Q9SS04)
brenda
Guo, L.; Yang, R.; Gu, Z.
Cloning of genes related to aliphatic glucosinolate metabolism and the mechanism of sulforaphane accumulation in broccoli sprouts under jasmonic acid treatment
J. Sci. Food. Agric.
96
4329-4336
2016
Brassica oleracea var. italica (A0A1P7ZDJ6), Brassica oleracea var. italica
brenda
Hansen, B.G.; Kliebenstein, D.J.; Halkier, B.A.
Identification of a flavin-monooxygenase as the S-oxygenating enzyme in aliphatic glucosinolate biosynthesis in Arabidopsis
Plant J.
50
902-910
2007
Arabidopsis thaliana (Q9SS04)
brenda
Li, J.; Hansen, B.G.; Ober, J.A.; Kliebenstein, D.J.; Halkier, B.A.
Subclade of flavin-monooxygenases involved in aliphatic glucosinolate biosynthesis
Plant Physiol.
148
1721-1733
2008
Arabidopsis thaliana (A8MRX0), Arabidopsis thaliana (Q93Y23), Arabidopsis thaliana (Q94K43), Arabidopsis thaliana (Q9SS04), Arabidopsis thaliana (Q9SXE1)
brenda
Li, Y.; Li, R.; Sawada, Y.; Boerzhijin, S.; Kuwahara, A.; Sato, M.; Hirai, M.Y.
Abscisic acid-mediated induction of FLAVIN-CONTAINING MONOOXYGENASE 2 leads to reduced accumulation of methylthioalkyl glucosinolates in Arabidopsis thaliana
Plant Sci.
303
110764
2021
Arabidopsis thaliana (Q93Y23), Arabidopsis thaliana (Q94K43), Arabidopsis thaliana, Arabidopsis thaliana Col-0 (Q93Y23), Arabidopsis thaliana Col-0 (Q94K43)
brenda
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