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Information on EC 2.3.3.17 - methylthioalkylmalate synthase
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EC Tree
2.3.3.17 methylthioalkylmalate synthaseIUBMB Comments
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.
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Word Map
- 2.3.3.17
- glucosinolate
- isopropylmalate
- brassicaceae
-
methionine-derived
- brassicae
- synthases
-
methylene
- leu
-
specialist
-
ecotype
-
branched-chain
- petraea
- oleracea
-
condensing
-
condenses
-
acetyl-coenzyme
- lyrata
-
generalist
- 4-methylthio-2-oxobutyrate
- indole
-
met-derived
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
methylthioalkylmalate synthase, mam synthase, methylthioalkylmalate synthase1, methylthioalkylmalate synthase 1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
MAM
MAM1
MAM2
MAM3
methylthioalkylmalate synthase 1
MAM1
-
-
-
-
MAM3
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an omega-(methylsulfanyl)-2-oxoalkanoate + acetyl-CoA + H2O = a 2-[omega-(methylsulfanyl)alkyl]malate + CoA
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
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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.
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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
2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O
2-(2'-methylthio)ethylmalate + CoA
-
-
-
?
2-oxoheptanoate + acetyl-CoA + H2O
2-pentylmalate + CoA
84% activity compared to 5-methylthio-2-oxopentanoate
-
-
?
2-oxohexanoate + acetyl-CoA + H2O
2-butylmalate + CoA
17% activity compared to 5-methylthio-2-oxopentanoate
-
-
?
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)-malate + CoA
-
-
-
?
4-methylthio-2-oxobutyrate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
-
-
-
?
7-methylthio-2-oxoheptanoate + acetyl-CoA + H2O
2-(5-methylthiopentyl)malate + CoA
substrate for isoform MAM3
-
-
?
9-methylthio-2-oxononanoate + acetyl-CoA + H2O
2-(7-methylthiohepyl)malate + CoA
substrate for isoform MAM3
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
-
-
-
?
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
86% activity compared to 5-methylthio-2-oxopentanoate
-
-
?
4-methylthio-2-oxobutanoate + acetyl-CoA + H2O
2-(2'-methylthioethyl)malate + CoA
substrate for isoforms MAM1, MAM2, and MAM3
-
-
?
5-methylthio-2-oxopentanoate + acetyl-CoA + H2O
2-(3'-methylthiopropyl)malate + CoA
-
-
-
?
5-methylthio-2-oxopentanoate + acetyl-CoA + H2O
2-(3'-methylthiopropyl)malate + CoA
100% activity
-
-
?
5-methylthio-2-oxopentanoate + acetyl-CoA + H2O
2-(3'-methylthiopropyl)malate + CoA
substrate for isoforms MAM1 and MAM3
-
-
?
6-methylthio-2-oxohexanoate + acetyl-CoA + H2O
2-(4-methylthiobutyl)malate + CoA
-
-
-
?
6-methylthio-2-oxohexanoate + acetyl-CoA + H2O
2-(4-methylthiobutyl)malate + CoA
-
-
-
?
6-methylthio-2-oxohexanoate + acetyl-CoA + H2O
2-(4-methylthiobutyl)malate + CoA
-
-
-
?
6-methylthio-2-oxohexanoate + acetyl-CoA + H2O
2-(4-methylthiobutyl)malate + CoA
low activity substrate for isoforms MAM1 and MAM3
-
-
?
8-methylthio-2-oxooctanoate + acetyl-CoA + H2O
2-(6-methylthiohexyl)malate + CoA
-
-
-
?
8-methylthio-2-oxooctanoate + acetyl-CoA + H2O
2-(6-methylthiohexyl)malate + CoA
substrate for isoform MAM3
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
additional information
?
-
2-oxo-dodecanoate is not a substrate for isoform MAM3
-
-
?
additional information
?
-
no activity with 6-methylthio-2-oxohexanoate, 2-oxopentanoate, 2-oxooctanoate, glyoxylate, pyruvate, 2-oxoisovalerate, 2-phenylpyruvate, oxaloacetate, 2-oxoglutarate, and 2-oxoadipate
-
-
?
additional information
?
-
-
no activity with 6-methylthio-2-oxohexanoate, 2-oxopentanoate, 2-oxooctanoate, glyoxylate, pyruvate, 2-oxoisovalerate, 2-phenylpyruvate, oxaloacetate, 2-oxoglutarate, and 2-oxoadipate
-
-
?
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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
2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O
2-(2'-methylthio)ethylmalate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
-
?
an omega-(methylthio)-2-oxoalkanoate + acetyl-CoA + H2O
a 2-[omega-(methylthio)alkyl]malate + CoA
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mn2+
additional information
additional information
Cu2+ and Zn2+ do not support catalysis at all
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
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
isoform MAM3 has no requirement for dithiothreitol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
32
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
isoform MAM3 catalyzes the formation of all glucosinolate chain lengths in vivo
metabolism
the enzyme catalyses the committing step of amino acid chain elongation in glucosinolate biosynthesis and plays an important role in determining the glucosinolate composition of Brassicaceae species, including Arabidopsis thaliana. MAM1 is responsible for homophenylalanine production
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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). MAM1_ARATH
506
0
55125
Swiss-Prot
Chloroplast (Reliability: 1)
MAM2_ARATH
506
0
55130
Swiss-Prot
Chloroplast (Reliability: 1)
MAM3_ARATH
503
0
55230
Swiss-Prot
Chloroplast (Reliability: 3)
A0A8E9ZR67_ISATI
504
0
54860
TrEMBL
Chloroplast (Reliability: 1)
A0A8E9ZQZ4_ISATI
499
0
54722
TrEMBL
Chloroplast (Reliability: 2)
A0A8E9ZSW0_ISATI
504
0
55419
TrEMBL
Chloroplast (Reliability: 1)
A0A0B5GPY2_BRAOA
387
0
42572
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
53000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
monomer
1 * 53000, isoform MAM3, calculated from amino acid sequence
monomer
1 * 53200, isoform MAM1, calculated from amino acid sequence
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A290G
the strain harbouring the MAM1 variant produces more thrice-elongated methionine than the native MAM1
A290S
unchanged composition of chain-elongated amino acids. The strain harbouring the MAM1 variant produces more thrice-elongated methionine than the native MAM1
A290T
G259A
T257C
the strain harbouring the MAM1 variant produces more thrice-elongated methionine than the native MAM1
T257D
in the strain harbouring the MAM1 variant, SSU3 protein level is higher than in the strain harbouring wild-type MAM1. The strain harbouring the MAM1 variant produces more thrice-elongated methionine than the native MAM1
T257G
the strain harbouring the MAM1 variant does not produce amino acids elongated more than twice
T257G/G259A
the strain harbouring the MAM1 variant produces tetra-elongated methionine
T257G/G259A/A290G
the strain harbouring the MAM1 variant produces tetra-elongated methionine. Unchanged composition of chain-elongated amino acids, although the production is dramatically reduced
T257G/G259A/L186M
the strain harbouring the MAM1 variant produces tetra-elongated methionine
T257N
T257S shows nearly 3fold higher L-homophenylalanine production than the native MAM1. In the strain harbouring the MAM1 variant, SSU3 protein level is higher than in the strain harbouring wild-type MAM1. Low levels of chain-elongated amino acid products are found
T257S
the strain harbouring the MAM1 variant shows higher MAM1 levels, although this does not result in correspondingly higher levels of chain-elongated products
A290T
in the strain harbouring the MAM1 variant, SSU3 protein level is higher than in the strain harbouring wild-type MAM1. No chain-elongated amino acid products are found
A290T
the strain harbouring the MAM1 variant does not produce any of the chain-elongated amino acid products
G259A
in the strain harbouring the MAM1 variant, SSU3 protein level is higher than in the strain harbouring wild-type MAM1. No chain-elongated amino acid products are found
G259A