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EC Tree
IUBMB 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 .
The taxonomic range for the selected organisms is: Escherichia coli The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
2-methylcitrate dehydratase, methylcitrate dehydratase, seprpd, 2-mc dehydratase,
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2-methylcitrate dehydratase
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methylcitrate dehydratase
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2-Methylcitrate hydro-lyase
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Dehydratase, 2-methylcitrate
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elimination of H2O
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(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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(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(E)-but-2-ene-1,2,3-tricarboxylate + H2O
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(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
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(2S,3S)-2-methylcitrate
cis-2-methylaconitate
(2S,3S)-2-methylcitrate
cis-2-methylaconitate + H2O
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(2S,3S)-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
cis-aconitate
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5fold lower activity than with 2-methylcitrate
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2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
additional information
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(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
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(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
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(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
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(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
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2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
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i.e. 2-methylcitrate, best substrate
i.e. 2-methyl-cis-aconitate
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2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
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metabolic function
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additional information
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(2R,3S)-isocitrate and citrate are poor substrates, no activity with trans-aconitate, threo-2-methylisocitrate, erythro-2-methylisocitrate, (S)-malate and (R)-malate
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additional information
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(2R,3S)-isocitrate and citrate are poor substrates, no activity with trans-aconitate, threo-2-methylisocitrate, erythro-2-methylisocitrate, (S)-malate and (R)-malate
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additional information
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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
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additional information
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substrate specificity, no activity with cis-aconitate and related substances containing double bonds, overview
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(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
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(2S,3S)-2-methylcitrate
cis-2-methylaconitate
the enzyme is involved in the methylcitric acid cycle
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(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
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2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
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metabolic function
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Fe2+
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enzyme possesses 1 unstable iron-sulfur center per monomer, required for activity, can be reconstituted by Fe2+ under reducing conditions
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propionate
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induces the enzyme expression from acnC and prpD
additional information
gene prpD, part of the prp operon, induction and expression depends on propionate during growth
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additional information
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gene prpD, part of the prp operon, induction and expression depends on propionate during growth
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0.44
(2S,3S)-2-methylcitrate
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0.005
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partially purified AcnC
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7 - 8
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for AcnC and PrpD
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SwissProt
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gene prpD, part of the prp operon, induction and expression depends on propionate during growth
SwissProt
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brenda
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physiological function
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
metabolism
the enzyme is involved in the 2-methylcitric acid cycle, overview
metabolism
the enzyme is involved in the methylcitric acid cycle
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54000
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gel filtration and native PAGE
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monomer
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1 * 54000, SDS-PAGE
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50
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half-life is 30 min for both AcnC and PrpD
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recombinant His-tagged enzyme from overexpressing strain
AcnC partially 0.25fold from AcnABnull strain, PrpD 14.3fold from overexpression in AcnABnull strain
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gene prpD, the mother cell metabolic gene (mmg) operon encodes homologues from the methylcitric acid cycle
genomic structure of prp operon, expression studies in Escherichia coli K12 strain W3350, and overexpression of the N-terminally His-tagged enzyme
DNA and amino acid sequence determination and analysis, genomic organization, expression of AcnC in AcnABnull strain, overexpression of PrpD in AcnABnull strain
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Brock, M.; Maerker, C.; Schuetz, A.; Voelker, U.; Buckel, W.
Oxidation of propionate to pyruvate in Escherichia coli: Involvement of methylcitrate dehydratase and aconitase
Eur. J. Biochem.
269
6184-6194
2002
Escherichia coli (P77243), Escherichia coli
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Blank, L.; Green, J.; Guest, J.R.
AcnC of Escherichia coli is a 2-methylcitrate dehydratase (PrpD) that can use citrate and isocitrate as substrates
Microbiology
148
133-146
2002
Escherichia coli
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Reddick, J.J.; Sirkisoon, S.; Dahal, R.A.; Hardesty, G.; Hage, N.E.; Booth, W.T.; Quattlebaum, A.L.; Mills, S.N.; Meadows, V.G.; Adams, S.L.H.; Doyle, J.S.; Kiel, B.E.
First biochemical characterization of a methylcitric acid cycle from Bacillus subtilis strain 168
Biochemistry
56
5698-5711
2017
Bacillus subtilis (P45859), Bacillus subtilis 168 (P45859), Escherichia coli (P77243), Escherichia coli, Escherichia coli K12 (P77243)
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Rocco, C.J.; Wetterhorn, K.M.; Garvey, G.S.; Rayment, I.; Escalante-Semerena, J.C.
The PrpF protein of Shewanella oneidensis MR-1 catalyzes the isomerization of 2-methyl-cis-aconitate during the catabolism of propionate via the AcnD-dependent 2-methylcitric acid cycle
PLoS ONE
12
e0188130
2017
Bacillus subtilis (P45859), Bacillus subtilis 168 (P45859), Escherichia coli (P77243), Salmonella enterica subsp. enterica serovar Typhimurium (P74840), Salmonella enterica subsp. enterica serovar Typhimurium LT2 / SGSC1412 / ATCC 700720 (P74840)
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