Information on EC 2.3.3.17 - methylthioalkylmalate synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.3.17
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RECOMMENDED NAME
GeneOntology No.
methylthioalkylmalate synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an omega-(methylsulfanyl)-2-oxoalkanoate + acetyl-CoA + H2O = a 2-[omega-(methylsulfanyl)alkyl]malate + CoA
show the reaction diagram
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
condensation
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;
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
aliphatic glucosinolate biosynthesis, side chain elongation cycle
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L-homomethionine biosynthesis
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Glucosinolate biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:omega-(methylthio)-2-oxoalkanoate C-acetyltransferase
The enzyme, characterized from the plant Arabidopsis thaliana, is involved in the L-methionine side-chain elongation pathway, forming substrates for the biosynthesis of aliphatic glucosinolates. Two forms are known - MAM1 catalyses only only the first two rounds of methionine chain elongation, while MAM3 catalyses all six cycles, up to formation of L-hexahomomethionine.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
isoform MAM3 catalyzes the formation of all glucosinolate chain lengths in vivo
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O
2-(2'-methylthio)ethylmalate + CoA
show the reaction diagram
-
-
-
?
2-oxoheptanoate + acetyl-CoA + H2O
2-pentylmalate + CoA
show the reaction diagram
84% activity compared to 5-methylthio-2-oxopentanoate
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-
?
2-oxohexanoate + acetyl-CoA + H2O
2-butylmalate + CoA
show the reaction diagram
17% activity compared to 5-methylthio-2-oxopentanoate
-
-
?
2-oxoisovalerate + acetyl-CoA
isopropylmalate + CoA
show the reaction diagram
-
-
-
?
4-methyl-2-oxopentanoate + acetyl-CoA
?
show the reaction diagram
-
-
-
?
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)-malate + CoA
show the reaction diagram
-
-
-
?
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
show the reaction diagram
4-methylthio-2-oxobutyrate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
show the reaction diagram
-
-
-
?
5-methyl-2-oxohexanoate + acetyl-CoA
?
show the reaction diagram
-
-
-
?
5-methylthio-2-oxopentanoate + acetyl-CoA
?
show the reaction diagram
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-
-
?
5-methylthio-2-oxopentanoate + acetyl-CoA + H2O
2-(3'-methylthiopropyl)malate + CoA
show the reaction diagram
5-methylthio-2-oxopentanoate + acetyl-CoA + H2O
?
show the reaction diagram
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-
-
?
6-methylthio-2-oxohexanoate + acetyl-CoA + H2O
2-(4-methylthiobutyl)malate + CoA
show the reaction diagram
7-methylthio-2-oxoheptanoate + acetyl-CoA + H2O
2-(5-methylthiopentyl)malate + CoA
show the reaction diagram
substrate for isoform MAM3
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-
?
8-methylthio-2-oxooctanoate + acetyl-CoA + H2O
2-(6-methylthiohexyl)malate + CoA
show the reaction diagram
9-methylthio-2-oxononanoate + acetyl-CoA
?
show the reaction diagram
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-
-
?
9-methylthio-2-oxononanoate + acetyl-CoA + H2O
2-(7-methylthiohepyl)malate + CoA
show the reaction diagram
substrate for isoform MAM3
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-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
show the reaction diagram
pyruvate + acetyl-CoA
citramalate + CoA
show the reaction diagram
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-
-
?
additional information
?
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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
2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O
2-(2'-methylthio)ethylmalate + CoA
show the reaction diagram
Q9FG67
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-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
activates nearly equivalent to Mn2+
Fe2+
activates nearly equivalent to Mn2+
Ni2+
activates nearly equivalent to Mn2+
additional information
Cu2+ and Zn2+ do not support catalysis at all
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
iodoacetamide
effective inhibitor, complete inhibition at 1 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ADP
the addition of ADP increases the rate of reaction over 10fold
ATP
the addition of 20 mM ATP increases the rate of reaction over 10fold
dithiothreitol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
2-oxoisovalerate
at pH 8.0 and 32C
0.932 - 3
4-methylthio-2-oxobutanoate
0.476 - 0.64
5-methylthio-2-oxopentanoate
0.463
6-methylthio-2-oxohexanoate
at pH 8.0 and 32C
0.253
8-methylthio-2-oxooctanoate
at pH 8.0 and 32C
0.081
9-methylthio-2-oxononanoate
at pH 8.0 and 32C
0.245 - 2.3
acetyl-CoA
8.6
pyruvate
at pH 8.0 and 32C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.18
2-oxoisovalerate
at pH 8.0 and 32C
1.3
4-methylthio-2-oxobutanoate
at pH 8.0 and 32C
1.3
5-methylthio-2-oxopentanoate
at pH 8.0 and 32C
2.5
6-methylthio-2-oxohexanoate
at pH 8.0 and 32C
0.3
8-methylthio-2-oxooctanoate
at pH 8.0 and 32C
0.03
9-methylthio-2-oxononanoate
at pH 8.0 and 32C
3
acetyl-CoA
at pH 8.0 and 32C
0.17
pyruvate
at pH 8.0 and 32C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
2-oxoisovalerate
at pH 8.0 and 32C
1.38
4-methylthio-2-oxobutanoate
at pH 8.0 and 32C
2.73
5-methylthio-2-oxopentanoate
at pH 8.0 and 32C
5.4
6-methylthio-2-oxohexanoate
at pH 8.0 and 32C
1.28
8-methylthio-2-oxooctanoate
at pH 8.0 and 32C
0.37
9-methylthio-2-oxononanoate
at pH 8.0 and 32C
1.3
acetyl-CoA
at pH 8.0 and 32C
0.023
pyruvate
at pH 8.0 and 32C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
18
ATP
Arabidopsis thaliana
Q9FN52
at pH 8.0 and 32C
0.01
EDTA
Arabidopsis thaliana
Q9FN52
at pH 8.0 and 32C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 9.2
50% activity at pH 6.3 and 9.0
7.4 - 9.7
50% activity at pH 7.4 and 9.7
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 39
70% activity at 25C and 39C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9
calculated from amino acid sequence
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
1 * 50000, SDS-PAGE
52000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
His Bind column chromatography; His Bind column chromatography; His Bind column chromatography
Ni-NTA agarose column chromatography; Ni-NTA agarose column chromatography
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Ni-NTA column chromatography
phenyl Sepharose column chromatography and Superdex 200 gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli DH5alpha cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is expressed throughout leaf development with lower transcript levels during the younger stages. The expression level of MAM1 is high at the vegetative-reproductive transition phase and significantly high in genotypes with high glucoraphanin content