Information on EC 2.5.1.19 - 3-phosphoshikimate 1-carboxyvinyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.5.1.19
-
RECOMMENDED NAME
GeneOntology No.
3-phosphoshikimate 1-carboxyvinyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
enolpyruvate group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
chorismate biosynthesis from 3-dehydroquinate
-
-
chorismate metabolism
-
-
Metabolic pathways
-
-
Phenylalanine, tyrosine and tryptophan biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
phosphoenolpyruvate:3-phosphoshikimate 5-O-(1-carboxyvinyl)-transferase
-
CAS REGISTRY NUMBER
COMMENTARY hide
9068-73-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain CP4
UniProt
Manually annotated by BRENDA team
strain CP4
UniProt
Manually annotated by BRENDA team
cyanobacterium
-
-
Manually annotated by BRENDA team
class II enzyme
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Bacteria ATX1398
strain ATX1398; selected from soil by its ability to grow in presence of the herbicide glyphosate
-
-
Manually annotated by BRENDA team
transgenic Brassica napus x Brassica juncea outcrossing are examined
-
-
Manually annotated by BRENDA team
; strain 435
SwissProt
Manually annotated by BRENDA team
strain 435
SwissProt
Manually annotated by BRENDA team
goosegrass
-
-
Manually annotated by BRENDA team
strain N5259
-
-
Manually annotated by BRENDA team
enzyme exists in 2 forms: one form is a monofunctional 59000 Da enzyme, the other form constitutes a single domain of the multifunctional 165000 Da arom protein
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
lettuce
-
-
Manually annotated by BRENDA team
Neurospora crassa 74-OR23-1A
strain 74-OR23-1A
-
-
Manually annotated by BRENDA team
cv. Speg et Comes, aneuploid cell line ANS-1
-
-
Manually annotated by BRENDA team
no activity in mammals
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
plant
maize
-
-
Manually annotated by BRENDA team
G2
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain A1501
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
spinach
-
-
Manually annotated by BRENDA team
wheat, cv. Maris Dove
-
-
Manually annotated by BRENDA team
mung bean
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
transgene inheritance and quantification upon wild Brassica juncea x transgenic Brassica napus outcrossing from three backcross generations and their progenies are examined using real-time PCR. Under in vitro conditions, a stable inheritance and similar cp4 epsps copy number between different generations and their progenies are shown. A marginally higher copy number is observed when Brassica juncea is used as the paternal as compared to when it is used as maternal parent
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-enolpyruvylshikimate 3-phosphate + H2O
5-enolpyruvylshikimate 3-phosphate ketal
show the reaction diagram
-
enzymatic hydrolysis, pH 7.0, 25C, in presence of phosphate scavenging system and excess of enzyme
-
-
?
phosphate + 5-enolpyruvylshikimate 3-phosphate
shikimate 3-phosphate + phosphoenolpyruvate
show the reaction diagram
-
reverse reaction
phosphoenolpyruvate generation coupled to pyruvate kinase and lactate dehydrogenase and monitored spectrophotometrically at 340 nm, pH7.0, in presence of ADP, NADH, MgCl2
-
r
phosphoenolpyruvate + 3-phosphoshikimate
?
show the reaction diagram
-
-
-
-
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
show the reaction diagram
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
show the reaction diagram
shikimate 3-phosphate + phosphoenolpyruvate
phosphate + 5-enolpyruvylshikimate 3-phosphate
show the reaction diagram
shikimate 3-phosphate + phosphoenolpyruvate
phosphate + 5-enpolpyruvylshikimate 3-phosphate
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
show the reaction diagram
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
slightly activating
CaCl2
-
stimulation at 20 mM, inhibition above 100 mM
Cs+
-
slightly activating
MgCl2
-
stimulation at 20 mM, inhibition above 100 mM
Na+
-
activates
NH4+
-
highly activating
Rb+
strong activation of forward reaction, effectiveness of activation in descending order: NH4Cl, Rb+, K+
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3R,4S,5R)-4-hydroxy-5-[(2R)-1-hydroxy-1-oxo-2-phosphono-propan-2-yl]oxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
(3R,4S,5R)-4-hydroxy-5-[(2S)-1-hydroxy-1-oxo-2-phosphono-propan-2-yl]oxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
(3R,4S,5R)-5-((R)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid
-
analogue of the tetrahedral reaction intermediate, competitive to both substrates, binding structure analysis, binding induces conformational changes to residues Arg124 and Glu341 within the active site, which results in structural alterations in the amino-terminal globular domain of the enzyme
(3R,4S,5R)-5-((S)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid
-
analogue of the tetrahedral reaction intermediate, competitive to both substrates, binding structure analysis, binding induces no conformational changes
(3R,4S,5R)-5-[(2R)-1,1-difluoro-3-hydroxy-3-oxo-2-phosphonooxy-propan-2-yl]oxy-4-hydroxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
(Z)-3-fluorophosphoenolpyruvate
-
competitive vs. phosphoenolpyruvate at saturated shikimate 3-phosphate concentration and vice versa
3-Bromopyruvate
5-Deoxy-shikimate 3-phosphate
-
competitive vs. shikimate 3-phosphate
5-enolpyruvylshikimate 3-phosphate
Al3+
-
10 mM, 37% inhibition
ammonium heptamolybdate
-
1.1 mM, 50% inhibition, no inhibition below 0.1 mM
Br-
-
inhibition above 200 mM, stimulation below
CaCl2
-
above 100 mM
Carboxyallenyl phosphate
-
strong
Cl-
-
inhibition above 400 mM, stimulation below
Co3+
-
10 mM, 25% inhibition
diethyldicarbonate
-
inactivation with a second-order rate constant of 220/M/min, subtstrates protect from inactivation, enzyme activity is recovered by treatment with hydroxylamine
glyphosate
I-
-
inhibition above 100 mM, stimulation below
La3+
-
10 mM, complete inhibition
MgCl2
-
above 100 mM
molybdate
-
10 mM, complete inhibition
N-ethylmaleimide
N-phosphonomethylglycine
NH4Cl
-
inhibition above 300 mM, stimulation below
NO3-
-
inhibition above 150 mM, stimulation below
Phenylglyoxal
phosphoenolpyruvate
pyruvate
-
20 mM, 85% inactivation after 1 h in the presence of cyanoborhydride, no inactivation in the absence of cyanoborhydride, preincubation with 5-enolpyruvylshikimate or a combination of shikimate 3-phosphate and glyphosate prevents from inactivation
Reaction intermediate analogue
-
-
-
shikimate 3-phosphate
-
product inhibition
shikimate 3-phosphate-5-carboxymethyl-(2R)-phosphonate
-
competitive vs. 5-enolpyruvylshikimate-3-phosphate and phosphate
shikimate 3-phosphate-5-carboxymethyl-(2S)-phosphonate
-
competitive vs. 5-enolpyruvylshikimate-3-phosphate and phosphate
SO42-
-
inhibition above 50 mM, slight stimulation below
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Br-
-
stimulation at low concentrations, inhibition above 200 mM
I-
-
stimulation at low concentrations, inhibition above 100 mM
SO42-
-
slight stimulation, inhibition above 50 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00036 - 2
3-phosphoshikimate
0.00025 - 2.5
5-enolpyruvylshikimate 3-phosphate
0.0018 - 24.8
phosphate
0.0024 - 43.6
phosphoenolpyruvate
0.02 - 0.43
shikimate 3-phosphate
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.026 - 100
3-phosphoshikimate
0.000012 - 7.4
5-enolpyruvylshikimate 3-phosphate
0.22 - 5.4
phosphate
0.0000045 - 100
phosphoenolpyruvate
additional information
5-enolpyruvylshikimate 3-phosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0016 - 910000000
3-phosphoshikimate
0.0007 - 930000000
phosphoenolpyruvate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000039 - 0.0018
(3R,4S,5R)-4-hydroxy-5-[(2R)-1-hydroxy-1-oxo-2-phosphono-propan-2-yl]oxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
0.00076 - 0.076
(3R,4S,5R)-4-hydroxy-5-[(2S)-1-hydroxy-1-oxo-2-phosphono-propan-2-yl]oxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
0.000016
(3R,4S,5R)-5-((R)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid
-
versus 3-phosphoshikimate
0.00075
(3R,4S,5R)-5-((S)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid
-
versus 3-phosphoshikimate
0.0000078 - 0.000063
(3R,4S,5R)-5-[(2R)-1,1-difluoro-3-hydroxy-3-oxo-2-phosphonooxy-propan-2-yl]oxy-4-hydroxy-3-phosphonooxy-cyclohexene-1-carboxylic acid
0.0029 - 0.0064
(Z)-3-fluorophosphoenolpyruvate
0.0126
5-Deoxy-shikimate 3-phosphate
-
-
0.0013
5-enolpyruvylshikimate 3-phosphate
-
-
0.0002 - 0.45
glyphosate
0.00008 - 0.96
N-phosphonomethylglycine
0.044
phosphoenolpyruvate
-
-
0.023
shikimate 3-phosphate
-
-
0.000015 - 0.00009
shikimate 3-phosphate-5-carboxymethyl-(2R)-phosphonate
0.0011 - 0.0021
shikimate 3-phosphate-5-carboxymethyl-(2S)-phosphonate
additional information
glyphosate
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00898 - 20
glyphosate
additional information
glyphosate
Escherichia coli
-
more than 10 mM for mutant G96A; more than 10 mM for mutant G96A/A183T
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0058
0.0064
-
recombinant enzyme, activity in crude extracts
0.0076
-
wild-type enzyme, cell exract
0.0357
-
mutant T42M, cell extract
0.19
-
bacterial extract
0.22
-
mutant N130S in bacterial extract
0.4
-
mutant G99A, after DEAE-Sepharose chromatography
0.57
-
mutant G99A, in crude bacterial extracts
0.62
-
mutant L104P, in crude bacterial extracts
0.63
-
mutant L104P, after DEAE-Sepharose chromatography
0.86
-
mutant G99A, after Superdex 200 gel filtration
1.26
-
reverse reaction, i.e. phosphate + 5-enolpyruvylshikimate 3-phosphate
1.34
-
mutant G99A, after ResourceQ chromatography
1.4
-
in crude bacterial extracts
1.7
-
after DEAE-sepharose chromatography
1.83
-
mutant L104P, after Superdex 200 gel filtration
1.91
-
mutant L104P, after ResourceQ chromatography
2
-
after Superdex 200 gel filtration
4.07
-
forward reaction, i.e. phosphoenolpyruvate + 3-phosphoshikimate
4.48
+/-0.79 micromol/min/mg, reconstituted G2-EPSPS (by intein-mediated protein complementation), mean specific activity, crude lysate from transformed Escherichia coli ER2799, malachite green dye assay
4.761
+/-0.92 micromol/min/mg, reconstituted G2-EPSPS (by intein-mediated protein complementation), maximum velocity, crude lysate from transformed Escherichia coli ER2799, malachite green dye assay
5.67
-
phosphate + 5-enolpyruvylshikimate 3-phosphate
5.68
-
activity of recombinant enzyme in crude extract
6.12
-
phosphate + 5-enolpyruvylshikimate 3-phosphate
7.12
+/-0.13 micromol/min/mg, full-length G2 EPSPS, mean specific activity, crude lysate from overexpressing Escherichia coli ER2799, malachite green dye assay
7.24
+/-0.16 micromol/min/mg, full-length G2 EPSPS, maximum velocity, crude lysate from overexpressing Escherichia coli ER2799, malachite green dye assay
8
-
+/-0.2 micromol/min/mg, mutant P101L
10.03
wild-type enzyme
10.23
mutant enzyme P106L
10.86
-
glyphosate insensitve strain
11.52
-
forward reaction, i.e. phosphoenolpyruvate + 3-phosphoshikimate
12
-
phosphoenolpyruvate + 3-phosphoshikimate
18.13
-
recombinant enzyme
18.9
-
mutant A183T, with respect to phosphoenolpyruvate
20
-
recombinant His-tagged wild-type enzyme
22
-
+/-0.4 micromol/min/mg, mutant P101S
24
-
recombinant wild-type enzyme
26.5
-
mutant G96A/A183T, with respect to phosphoenolpyruvate
28
-
+/-1 micromol/min/mg, mutant P101G
31
-
+/-0.5 micromol/min/mg, mutant P101A
34
-
with respect to phosphoenolpyruvate
35.9
-
Vmax
37.4
-
mutant G96A, with respect to phosphoenolpyruvate
47.5
plant
-
Vmax
50
-
+/-1 micromol/min/mg
61
-
isoenzyme I
94.7
-
isoenzyme II
additional information
-
activity of isoenzyme II increases in elicited cells
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.4
-
wild-type enzyme, 2 maxima at pH 5.4 and pH 7.0
5.6
-
phosphate + 5-enolpyruvylshikimate 3-phosphate, 2 maxima at pH 5.6 and pH 7.6
6
-
glyphosate-resistant enzyme, 2 maxima at pH 6 and pH 7.3
7 - 7.2
-
50% of maximal activity between pH 6.2 and pH 8.5
7.3
-
glyphosate-resistant enzyme, 2 maxima at pH 6 and pH 7.3
7.4
-
Tris-HCl buffer preferred
7.4 - 7.5
-
isoenzymes I and II
7.5
-
assay at
7.6
-
phosphate + 5-enolpyruvylshikimate 3-phosphate, 2 maxima, at pH 5.6 and pH 7.6
7.8
-
wild-type enzyme
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 8.5
-
approx. half-maximal activity at pH 5.0 and 8.5
5.5 - 8.7
-
approx. half-maximal activity at pH 5.5 and 8.7, phosphate + 5-enolpyruvylshikimate 3-phosphate
5.6 - 8.4
-
H385N mutantt enzyme
6 - 8.4
-
wild-type enzyme
6.2 - 8.5
-
approx. half-maximal activity at pH 6.2 and 8.5
6.5 - 8.5
-
approx. half-maximal activity at pH 6.5 and 8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
-
assay at
55
-
isoenzymes I and II
60
-
wild-type enzyme
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45 - 62
-
approx. half-maximal activity at 45C and 62C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.22
calculated from sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
constitutively expressed, low expression
Manually annotated by BRENDA team
constitutively expressed
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
multifunctional enzyme form i.e. single domain of arom protein
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Acinetobacter baumannii (strain ATCC 17978 / CIP 53.77 / LMG 1025 / NCDC KC755 / 5377)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Agrobacterium sp. (strain CP4)
Bacillus halodurans (strain ATCC BAA-125 / DSM 18197 / FERM 7344 / JCM 9153 / C-125)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Coxiella burnetii (strain RSA 493 / Nine Mile phase I)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20400
C-terminal fragment (from Thr296) expressed in pKEB12, Western blot
32400
-
gel filtration
42000
-
gel filtration
46000
-
wild-type and mutant N130S, SDS-PAGE on bacterial extracts
46110
-
calculated from polypeptide sequence of aroA gene product
46430
by ESI-MS; deduced from primary structure
47000
full-length protein, Western blot analyses
48000
-
mixture of monomers and dimers in the absence of NH4Cl, only monomers in the presence of NH4Cl, gel filtration
50000
-
wild-type and mutants, SDS-PAGE after induced overexpression in Escherichia coli
54040
-
deduced from primary sequence
54600
deduced from primary structure, 514 amino acids
55000
-
gel filtration
57000
-
gel filtration
58100
-
isoenzyme II, gel filtration
58700
-
isoenzyme I, gel filtration
59000
-
monofunctional enzyme
73000
overexpressed mature protein (47000 Da) with GST tag (26000 Da)
91000
-
gel filtration
159000
-
multifunctional enzyme called arom
290000
-
aromatic multifunctional enzyme protein, sedimentation equilibrium analysis
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 49000, SDS-PAGE
monomer