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Information on EC 4.2.1.79 - 2-methylcitrate dehydratase
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EC Tree
4.2.1.79 2-methylcitrate dehydrataseIUBMB Comments
The enzyme is specific for (2S,3S)-methylcitrate, showing no activity with (2R,3S)-methylcitrate . The enzyme can also use cis-aconitate as a substrate but more slowly . Both this enzyme and EC 4.2.1.3, aconitate hydratase, are required to complete the isomerization of (2S,3S)-methylcitrate to (2R,3S)-2-methylisocitrate .
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Word Map
- 4.2.1.79
- propionate
- propionyl-coa
- enterica
- isocitrate
- tuberculosis
- methylisocitrate
- oneidensis
- cis-aconitate
-
prpbcde
-
odd-chain
-
shewanella
- glyoxylate
- prpf
-
beta-oxidation
-
serovar
- smegmatis
-
propionyl
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
Synonyms
2-methylcitrate dehydratase, methylcitrate dehydratase, seprpd, 2-mc dehydratase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-MC dehydratase
2-methylcitrate dehydratase
2-methylcitrate dehydratase 1
2-Methylcitrate hydro-lyase
-
-
-
-
Dehydratase, 2-methylcitrate
-
-
-
-
methylcitrate dehydratase
mmgE
PrpD
SePrpD
STM0370
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
addition
elimination of H2O
-
-
-
-
addition
-
-
double bond
-
addition
-
-
of H2O to double bond
-
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SYSTEMATIC NAME
IUBMB Comments
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate hydro-lyase [(Z)-but-2-ene-1,2,3-tricarboxylate-forming]
The enzyme is specific for (2S,3S)-methylcitrate, showing no activity with (2R,3S)-methylcitrate [2]. The enzyme can also use cis-aconitate as a substrate but more slowly [2]. Both this enzyme and EC 4.2.1.3, aconitate hydratase, are required to complete the isomerization of (2S,3S)-methylcitrate to (2R,3S)-2-methylisocitrate [2].
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CAS REGISTRY NUMBER
COMMENTARY
80891-26-5
-
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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-Hydroxybutane-1,2,3-tricarboxylate
?
-
methylcitric acid cycle, propionyl-CoA oxidation
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(E)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(E)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(E)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
Salmonella enterica subsp. enterica serovar Typhimurium LT2 / SGSC1412 / ATCC 700720
-
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate
-
-
?
(2S,3S)-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
i.e. 2-methylcitrate, highly specific for, stereospecific for (2S,3S)-methylcitrate, the reverse reaction is an unusual syn-elimination
i.e. 2-methyl-cis-aconitate
?
(2S,3S)-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
enzyme performs the isomerization of (2S,3S)-methylcitrate to (2R,3S)-2-methylisocitrate together with aconitase, both enzymes are essential, overview
-
r
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
2-Hydroxybutane-1,2,3-tricarboxylate
-
r
r, i.e. 2-methylcitrate
?
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
2-Hydroxybutane-1,2,3-tricarboxylate
-
i.e. 2-methyl-cis-aconitate
r, i.e. 2-methylcitrate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate, best substrate
i.e. 2-methyl-cis-aconitate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
metabolic function
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate
i.e. 2-methyl-cis-aconitate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
i.e. 2-methylcitrate
i.e. 2-methyl-cis-aconitate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate, best substrate
i.e. 2-methyl-cis-aconitate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate, best substrate
i.e. 2-methyl-cis-aconitate
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
r
r
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
i.e. 2-methylcitrate
r
?
cis-aconitate
?
5fold lower activity than with 2-methylcitrate
-
?
additional information
?
-
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate, but the physiological pathways proceed via (Z)-2-methylaconitate, which serves as the substrate for the citB enzyme in the synthesis of 2-methylisocitrate
-
-
?
additional information
?
-
the MmgE enzyme is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate, but the physiological pathways proceed via (Z)-2-methylaconitate, which serves as the substrate for the citB enzyme in the synthesis of 2-methylisocitrate
-
-
?
additional information
?
-
(2R,3S)-isocitrate and citrate are poor substrates, no activity with trans-aconitate, threo-2-methylisocitrate, erythro-2-methylisocitrate, (S)-malate and (R)-malate
-
?
additional information
?
-
-
(2R,3S)-isocitrate and citrate are poor substrates, no activity with trans-aconitate, threo-2-methylisocitrate, erythro-2-methylisocitrate, (S)-malate and (R)-malate
-
?
additional information
?
-
-
substrate specificity, no activity with cis-aconitate and related substances containing double bonds, overview
-
?
additional information
?
-
the PrpD enzyme from Escherichia coli is not a stereospecific 2-methylcitrate dehydratase because it can dehydrate at least two of the four diastereomers of 2-methylcitrate to yield either (E)-2-methylaconitate or (Z)-2-methylaconitate, but the physiological pathways proceed via (Z)-2-methylaconitate, which serves as the substrate for the citB enzyme in the synthesis of 2-methylisocitrate
-
-
?
additional information
?
-
-
enzyme of the methylcitrate cycle
-
-
?
additional information
?
-
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
-
enzyme of the methylcitrate cycle
-
-
?
additional information
?
-
enzyme does not catalyze the hydration of 2-methyl-cis-aconitate to 2-methylisocitrate, isocitrate is no substrate
-
?
additional information
?
-
-
enzyme does not catalyze the hydration of 2-methyl-cis-aconitate to 2-methylisocitrate, isocitrate is no substrate
-
?
additional information
?
-
the enzyme and the aconitase perform the 2-methylcitric acid cycle, overview
-
?
additional information
?
-
-
the enzyme and the aconitase perform the 2-methylcitric acid cycle, overview
-
?
additional information
?
-
-
PrpD does not catabolize 2-methylcitrate which is produced by the Krebs cycle enzyme citrate synthase GltA
-
-
?
additional information
?
-
-
PrpD does not catabolize 2-methylcitrate which is produced by the Krebs cycle enzyme citrate synthase GltA
-
-
?
additional information
?
-
-
2-methylisocitrate and isocitrate are no substrates for AcnD
-
?
additional information
?
-
-
2-methylisocitrate and isocitrate are no substrates for AcnD
-
?
additional information
?
-
-
not: citrate, threo-DL-isocitrate, threo-D-2-methylisocitrate, DL-homocitrate, DL-citramalate
-
-
?
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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
(2S,3S)-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
enzyme performs the isomerization of (2S,3S)-methylcitrate to (2R,3S)-2-methylisocitrate together with aconitase, both enzymes are essential, overview
-
r
2-Hydroxybutane-1,2,3-tricarboxylate
?
-
methylcitric acid cycle, propionyl-CoA oxidation
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
Salmonella enterica subsp. enterica serovar Typhimurium LT2 / SGSC1412 / ATCC 700720
-
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
metabolic function
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
-
-
-
?
additional information
?
-
-
enzyme of the methylcitrate cycle
-
-
?
additional information
?
-
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
-
enzyme of the methylcitrate cycle
-
-
?
additional information
?
-
the enzyme and the aconitase perform the 2-methylcitric acid cycle, overview
-
?
additional information
?
-
-
the enzyme and the aconitase perform the 2-methylcitric acid cycle, overview
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
the enzyme contains no iron-sulfur center
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
additional information
Fe2+
-
enzyme possesses 1 unstable iron-sulfur center per monomer, required for activity, can be reconstituted by Fe2+ under reducing conditions
Fe2+
-
AcnD enzyme possesses 1 unstable iron-sulfur center per monomer, absolutely required for activity, can be reconstituted by Fe2+ under reducing conditions
Fe2+
-
AcnD enzyme possesses 1 unstable iron-sulfur center per monomer, absolutely required for activity, can be reconstituted by Fe2+ under reducing conditions
additional information
no requirement for metal ions and reducing agents
additional information
-
no requirement for metal ions and reducing agents
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
propionate
-
induces enzyme expression, enzyme is required for growth on propionate
propionate
-
induces enzyme expression, enzyme is required for growth on propionate
PrpF
-
seems to be an accessory protein required to prevent oxidative damage of the Fe/S center of active AcnD enzyme, or is involved in synthesis or repair of the Fe/S cluster present in AcnD
-
PrpF
-
seems to be an accessory protein required to prevent oxidative damage of the Fe/S center of active AcnD enzyme, or is involved in synthesis or repair of the Fe/S cluster present in AcnD
-
additional information
gene prpD, part of the prp operon, induction and expression depends on propionate during growth
-
additional information
-
gene prpD, part of the prp operon, induction and expression depends on propionate during growth
-
additional information
-
no requirement for AMP, ADT, ATP, NAD(P)+, NAD(P)H, pyruvate
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
Proteomic comparison of Mycobacterium avium subspecies paratuberculosis grown in vitro and isolated from clinical cases of ovine paratuberculosis.
Tuberculosis
Dual role of isocitrate lyase 1 in the glyoxylate and methylcitrate cycles in Mycobacterium tuberculosis.
Tuberculosis
Role of the methylcitrate cycle in Mycobacterium tuberculosis metabolism, intracellular growth, and virulence.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2.6
purified recombinant His-tagged enzyme, substrate cis-aconitate
2.8
purified recombinant His-tagged enzyme, substrate 2-methylcitrate
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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
25 - 37
37
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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
Salmonella enterica subsp. enterica serovar Typhimurium LT2 / SGSC1412 / ATCC 700720
-
UniProt
brenda
gene acnD and prpF are both needed for full enzyme activity, they exist in place of or in addition to prpD
-
-
brenda
gene acnD and prpF are both needed for full enzyme activity, they exist in place of or in addition to prpD
-
-
brenda
<