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EC Tree
IUBMB Comments The enzyme is involved in the biosynthesis of several siderophores, such as 2,3-dihydroxybenzoylglycine, enterobactin, bacillibactin, and vibriobactin.
The taxonomic range for the selected organisms is: Escherichia coli The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
isochorismatase, isoc2, isochorismatase hydrolase, 2,3-dihydro-2,3-dihydroxybenzoate synthase, isochorismatase domain containing 2,
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EntB
contains an N-terminal isochorismate lyase domain
2,3 dihydro-2,3 dihydroxybenzoate synthase
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2,3-dihydro-2,3-dihydroxybenzoate synthase
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2,3-dihydroxy-2,3-dihydrobenzoate synthase
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2,3-dihydroxy-2,3-dihydrobenzoic synthase
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isochorismate pyruvate-hydrolase
The enzyme is involved in the biosynthesis of several siderophores, such as 2,3-dihydroxybenzoylglycine, enterobactin, bacillibactin, and vibriobactin.
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(+/-)-3-[(1-carboxyethenyl)oxy]-2-hydroxy-6-cyclohexene-1-carboxylic acid + H2O
3,4-dihydroxy-cyclohex-1-enecarboxylic acid + pyruvate
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?
(+/-)-3-[(1-carboxyethenyl)oxy]-cyclohepta-1,6-diene-1-carboxylate + H2O
(S)-3-hydroxy-cyclohepta-1,6-dienecarboxylic acid + pyruvate
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i.e. (S)-3-(1-carboxyvinyloxy)-cyclohepta-1,6-dienecarboxylic acid
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(+/-)-3-[(carboxyethenyl)oxy]-1-cyclohexene-1-carboxylic acid + H2O
(S)-3-hydroxycyclohex-1-enecarboxylic acid + pyruvate
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?
(+/-)-cis-3-[(carboxyethenyl)oxy]-4-cyclohexene-1-carboxylic acid + H2O
(R)-5-hydroxycyclohex-3-enecarboxylic acid + pyruvate
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chorismate + H2O
3,4-dihydroxy-cyclohexa-1,5-dienecarboxylic acid + pyruvate
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slow hydrolysis
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?
isochorismate + H2O
(2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
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isochorismate + H2O
2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
isochorismate + H2O
2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
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?
isochorismate + H2O
2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
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biosynthesis of enterobactin
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?
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isochorismate + H2O
(2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
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isochorismate + H2O
2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
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biosynthesis of enterobactin
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?
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(+/-)-3-[(carboxyethenyl)oxy]-6-hydroxy-1-benzoic acid
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i.e. 5-(1-carboxyvinyloxy)-2-hydroxybenzoic acid
3-[(carboxyethenyl)oxy]benzoic acid
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i.e. 3-(1-carboxyvinyloxy)benzoic acid
disodium 3-(2-carboxylatoethyl)benzoate
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disodium 3-[(E)-2-carboxylatoethenyl]benzoate
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0.023
(+/-)-3-[(1-carboxyethenyl)oxy]-2-hydroxy-6-cyclohexene-1-carboxylic acid
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0.12
(+/-)-3-[(1-carboxyethenyl)oxy]-cyclohepta-1,6-diene-1-carboxylate
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0.086
(+/-)-3-[(carboxyethenyl)oxy]-1-cyclohexene-1-carboxylic acid
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0.28
(+/-)-cis-3-[(carboxyethenyl)oxy]-4-cyclohexene-1-carboxylic acid
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5.17
(+/-)-3-[(1-carboxyethenyl)oxy]-2-hydroxy-6-cyclohexene-1-carboxylic acid
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9
(+/-)-3-[(1-carboxyethenyl)oxy]-cyclohepta-1,6-diene-1-carboxylate
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21.7
(+/-)-3-[(carboxyethenyl)oxy]-1-cyclohexene-1-carboxylic acid
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16.3
(+/-)-cis-3-[(carboxyethenyl)oxy]-4-cyclohexene-1-carboxylic acid
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0.282
disodium 3-(2-carboxylatoethyl)benzoate
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pH and temperature not specified in the publication
0.122
disodium 3-[(E)-2-carboxylatoethenyl]benzoate
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pH and temperature not specified in the publication
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0.472
disodium 3-(2-carboxylatoethyl)benzoate
Escherichia coli
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pH and temperature not specified in the publication
0.209
disodium 3-[(E)-2-carboxylatoethenyl]benzoate
Escherichia coli
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pH and temperature not specified in the publication
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Uniprot
brenda
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predominantly
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small fraction membrane-bound, predominantly cytosolic
brenda
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33090
calculated molecular mass
33100
determinecd by MALDI-TOF spectrometry
32554
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5 * 32554, sequence of DNA
35000
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5 * 35000, SDS-PAGE
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pentamer
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5 * 32554, sequence of DNA
pentamer
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5 * 35000, SDS-PAGE
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the crystal structure of the EntB protein is determined at a resolution of 2.3 A
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D227R
mutant constructed for functional analysis of EntB-EntE interaction
D240R
mutant constructed for functional analysis of EntB-EntE interaction
D244R
mutant constructed for functional analysis of EntB-EntE interaction
D263R
mutant constructed for functional analysis of EntB-EntE interaction
F264E
mutant constructed for functional analysis of EntB-EntE interaction
I239D
mutant constructed for functional analysis of EntB-EntE interaction
K269E
mutant constructed for functional analysis of EntB-EntE interaction
M249E
mutant constructed for functional analysis of EntB-EntE interaction
R247E
mutant constructed for functional analysis of EntB-EntE interaction
S245A
mutant constructed for functional analysis of EntB-EntE interaction
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-20°C, 25 mM Tris buffer, pH 8.0, 5 mM dithiothreitol, 50% glycerol, stable for several months
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purification is obtained by two metal chelate chromatography steps seperated by emoval of the His tag with TEV protease
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into the pGEM7z and the pET15bTEV vector for expression in Escherichia coli BL21DE3 cells
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Rusnak, F.; Liu, J.; Quinn, N.; Berchtold, G.A.; Walsh, C.T.
Subcloning of the enterobactin biosynthetic gene entB: expression, purification, characterization, and substrate specificity of isochorismatase
Biochemistry
29
1425-1435
1990
Escherichia coli
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Nahlik, M.S.; Fleming, T.P.; McIntosh, M.A.
Cluster of genes controlling synthesis and activation of 2,3-dihydroxybenzoic acid in production of enterobactin in Escherichia coli
J. Bacteriol.
169
4163-4170
1987
Escherichia coli
brenda
Hantash, F.M.; Earhart, C.F.
Membrane association of the Escherichia coli enterobactin synthase proteins EntB/G, EntE, and EntF
J. Bacteriol.
182
1768-1773
2000
Escherichia coli
brenda
Drake, E.J.; Nicolai, D.A.; Gulick, A.M.
Structure of the EntB multidomain nonribosomal peptide synthetase and functional analysis of its interaction with the EntE adenylation domain
Chem. Biol.
13
409-419
2006
Escherichia coli (P0ADI4)
brenda
Hubrich, F.; Mordhorst, S.; Andexer, J.N.
Cinnamic acid derivatives as inhibitors for chorismatases and isochorismatases
Bioorg. Med. Chem. Lett.
23
1477-1481
2013
Escherichia coli
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