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(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-methylcitrate
cis-2-methylaconitate
(2S,3S)-2-methylcitrate
cis-2-methylaconitate + H2O
-
-
-
?
(2S,3S)-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
2-Hydroxybutane-1,2,3-tricarboxylate
2-Hydroxybutane-1,2,3-tricarboxylate
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
2-Hydroxybutane-1,2,3-tricarboxylate
?
-
methylcitric acid cycle, propionyl-CoA oxidation
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
citrate
cis-aconitate + H2O
additional information
?
-
(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
-
-
-
?
(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
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
?
cis-aconitate
?
5fold lower activity than with 2-methylcitrate
-
?
citrate
?
-
-
-
?
citrate
?
low activity with
-
?
citrate
cis-aconitate + H2O
-
-
-
?
citrate
cis-aconitate + H2O
-
-
-
?
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
?
-
-
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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(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
(Z)-but-2-ene-1,2,3-tricarboxylate + H2O
(2S,3S)-2-methylcitrate
cis-2-methylaconitate
(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
(Z)-But-2-ene-1,2,3-tricarboxylate + H2O
2-Hydroxybutane-1,2,3-tricarboxylate
?
-
methylcitric acid cycle, propionyl-CoA oxidation
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
additional information
?
-
(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
-
-
-
?
(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
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
?
2-methylcitrate
2-methyl-cis-aconitate + H2O
-
-
-
?
additional information
?
-
-
enzyme of the methylcitrate cycle
-
-
?
additional information
?
-
-
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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metabolism
-
2-methylcitrate dehydratase and 1, 2-methylcitrate synthase are involved in energy metabolism and participate in the methylcitrate cycle, which is an important source of energy in the cell
metabolism
the enzyme is involved in the 2-methylcitric acid cycle, overview
metabolism
the enzyme is involved in the 2-methylcitric acid cycle, overview
metabolism
the enzyme is involved in the 2-methylcitric acid cycle, overview. The three genes, mmgDE and yqiQ (mmgF), provide three of the five steps of the methylcitric acid cycle, encoded in the mmg operon. The fourth step can be supplied by citB (aconitase), and the fifth probably missing step, the propionyl-CoA synthetase, is probably skipped because the beta-oxidation of methyl-branched fatty acids by the enzymes encoded by mmgABC produce propionyl-CoA. The 2-methylisocitrate produced by CitB is converted to pyruvate and succinate by the enzyme YqiQ(MmgF)
metabolism
the enzyme is involved in the methylcitric acid cycle
metabolism
the enzyme is involved in the methylcitric acid cycle
metabolism
-
the enzyme is involved in the methylcitric acid cycle
-
metabolism
-
the enzyme is involved in the 2-methylcitric acid cycle, overview. The three genes, mmgDE and yqiQ (mmgF), provide three of the five steps of the methylcitric acid cycle, encoded in the mmg operon. The fourth step can be supplied by citB (aconitase), and the fifth probably missing step, the propionyl-CoA synthetase, is probably skipped because the beta-oxidation of methyl-branched fatty acids by the enzymes encoded by mmgABC produce propionyl-CoA. The 2-methylisocitrate produced by CitB is converted to pyruvate and succinate by the enzyme YqiQ(MmgF)
-
metabolism
-
2-methylcitrate dehydratase and 1, 2-methylcitrate synthase are involved in energy metabolism and participate in the methylcitrate cycle, which is an important source of energy in the cell
-
metabolism
-
the enzyme is involved in the 2-methylcitric acid cycle, overview
-
metabolism
-
the enzyme is involved in the methylcitric acid cycle
-
physiological function
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
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
physiological function
-
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
-
ipon silver stess 2-methylcitrate dehydratase and 2-methylcitrate synthase are strongly overexpressed
additional information
construction of enzyme-deficient DELTA prpD mutant. The two genes acnD and prpF, encoding 2-methylcitrate dehydratase (AcnD, EC 4.2.1.117) and 2-methyl-aconitate isomerase (SoPrpF, EC 5.3.3.-) from Shewanella oneidensis together can replace gene prpD in Salmonella enterica. SoAcnD and SePrpD synthesize different methylaconitate isomers. The SoPrpF protein isomerizes the product of the AcnD reaction into the PrpD product. Mutant SoPrpF variants with substitutions of residues K73 or C107 fail to support growth with propionate as the sole source of carbon and energy
additional information
-
ipon silver stess 2-methylcitrate dehydratase and 2-methylcitrate synthase are strongly overexpressed
-
additional information
-
construction of enzyme-deficient DELTA prpD mutant. The two genes acnD and prpF, encoding 2-methylcitrate dehydratase (AcnD, EC 4.2.1.117) and 2-methyl-aconitate isomerase (SoPrpF, EC 5.3.3.-) from Shewanella oneidensis together can replace gene prpD in Salmonella enterica. SoAcnD and SePrpD synthesize different methylaconitate isomers. The SoPrpF protein isomerizes the product of the AcnD reaction into the PrpD product. Mutant SoPrpF variants with substitutions of residues K73 or C107 fail to support growth with propionate as the sole source of carbon and energy
-
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Aoki, H.; Nakahara, T.; Tabuchi, T.
2-Methylcitrate dehydratase, a new enzyme of propionate metabolism in Saccharomycopsis lipolytica
Curr. Dev. Yeast Res. , Proc. Int. Yeast Symp. (Stewart, G. G. , Russel, I. , eds. ) Pergamon, Toronto
435-439
1980
Yarrowia lipolytica
-
brenda
Aoki, H.; Tabuchi, T.
Purification and properties of 2-methylcitrate dehydratase from Yarrowia lipolytica
Agric. Biol. Chem.
45
2831-2837
1981
Yarrowia lipolytica
-
brenda
Tabuchi, T.; Aoki, H.; Uchiyama, H.; Nakahara, T.
2-Methylcitrate dehydratase, a new enzyme functioning at the methylcitric acid cycle of propionate metabolism
Agric. Biol. Chem.
45
2823-2929
1981
Yarrowia lipolytica
-
brenda
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
brenda
Gulick, A.M.; Horswill, A.R.; Thoden, J.B.; Escalante-Semerena, J.C.; Rayment, I.
Pentaerythritol propoxylate: a new crystallization agent and cryoprotectant induces crystal growth of 2-methylcitrate dehydratase
Acta Crystallogr. Sect. D
58
306-309
2002
Salmonella enterica
brenda
Horswill, A.R.; Escalante-Semerena, J.C.
In vitro conversion of propionate to pyruvate by Salmonella enterica enzymes: 2-methylcitrate dehydratase (PrpD) and aconitase Enzymes catalyze the conversion of 2-methylcitrate to 2-methylisocitrate
Biochemistry
40
4703-4713
2001
Salmonella enterica (P74840), Salmonella enterica
brenda
Grimek, T.L.; Escalante-Semerena, J.C.
The acnD genes of Shewenella oneidensis and Vibrio cholerae encode a new Fe/S-dependent 2-methylcitrate dehydratase enzyme that requires prpF function in vivo
J. Bacteriol.
186
454-462
2004
Shewanella oneidensis, Vibrio cholerae serotype O1
brenda
Blank, L.; Green, J.; Guest, J.R.
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