Information on EC 2.1.1.150 - isoflavone 7-O-methyltransferase

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The expected taxonomic range for this enzyme is: Medicago

EC NUMBER
COMMENTARY hide
2.1.1.150
-
RECOMMENDED NAME
GeneOntology No.
isoflavone 7-O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + a 7-hydroxyisoflavone = S-adenosyl-L-homocysteine + a 7-methoxyisoflavone
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
isoflavonoid biosynthesis I
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isoflavonoid biosynthesis II
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Isoflavonoid biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:hydroxyisoflavone 7-O-methyltransferase
The enzyme from alfalfa can methylate daidzein, genistein and 6,7,4'-trihydroxyisoflavone but not flavones or flavanones.
CAS REGISTRY NUMBER
COMMENTARY hide
136111-54-1
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55071-80-2
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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
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
show the reaction diagram
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
show the reaction diagram
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methylisoflavone
show the reaction diagram
preferred substrate
-
-
?
S-adenosyl-L-methionine + 7,2'-dihydroxy-4'-methoxyisoflavone
S-adenosyl-L-homocysteine + 2-hydroxy-7,4'-dimethoxyisoflavone
show the reaction diagram
-
i.e. 2'-hydroxyformononetin. 55% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
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-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
show the reaction diagram
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
show the reaction diagram
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
show the reaction diagram
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
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
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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enzyme activity was not affected by inclusion of 5 mM Mn2+, Mg2+, or EDTA in the assay mixture
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dithioerythritol
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10-20 mM, up to 39% inhibition
dithiothreitol
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10-20 mM, up to 39% inhibition
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0011
isorhamnetin
Populus deltoides
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1977
0.0015
kaempferol
Populus deltoides
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408
0.0025
luteolin
Populus deltoides
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-
436
0.0022
quercetin
Populus deltoides
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-
137
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
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pH 8.5, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
8.7
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glycine-NaOH buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.3
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IOMT IIB, chromatography
4.9
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IOMT IIA, chromatography
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 39603, calculated from sequence; x * 41000, SDS-PAGE
homodimer
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monomer
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1 * 41000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method. Crystal structure of IOMT in complex with the products S-adenosyl-L-homocysteine and isoformononetin (4'-hydroxy-7-methoxyisoflavone) refined to 1.4 A
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
stabilized in the presence of EDTA and thiol-containing reagents
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
treatment of alfalfa cell suspension cultures with elicitor preparations from Saccharomyces cerevisiae or from cell walls of Colletotrichum lindemuthianum results in a ca 200fold induction of isoflavone 0-methyltransferase activity
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
up
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IOMT transcripts are rapidly induced following elicitation, prior to the increase in IOMT activity