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
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Biosynthesis of secondary metabolites
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chorismate biosynthesis from 3-dehydroquinate
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Metabolic pathways
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Phenylalanine, tyrosine and tryptophan biosynthesis
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chorismate metabolism
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SYSTEMATIC NAME
IUBMB Comments
phosphoenolpyruvate:3-phosphoshikimate 5-O-(1-carboxyvinyl)-transferase
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CAS REGISTRY NUMBER
COMMENTARY hide
9068-73-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain CP4
UniProt
Manually annotated by BRENDA team
strain CP4
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
cyanobacterium
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-
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
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Manually annotated by BRENDA team
transgenic Brassica napus x Brassica juncea outcrossing are examined
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Manually annotated by BRENDA team
; strain 435
SwissProt
Manually annotated by BRENDA team
strain 435
SwissProt
Manually annotated by BRENDA team
strain N5259
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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
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
lettuce
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Manually annotated by BRENDA team
Lyngbya sp.
-
-
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain 74-OR23-1A
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-
Manually annotated by BRENDA team
cv. Speg et Comes, aneuploid cell line ANS-1
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Manually annotated by BRENDA team
no activity in mammals
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
plant
maize
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain A1501
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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A0A0139XBW5
UniProt
Manually annotated by BRENDA team
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A0A0139XBW5
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
spinach
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Tolypothrix sp.
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UniProt
Manually annotated by BRENDA team
wheat, cv. Maris Dove
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Manually annotated by BRENDA team
mung bean
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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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
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enzymatic hydrolysis, pH 7.0, 25C, in presence of phosphate scavenging system and excess of enzyme
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-
?
phosphate + 5-enolpyruvylshikimate 3-phosphate
shikimate 3-phosphate + phosphoenolpyruvate
show the reaction diagram
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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
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r
phosphoenolpyruvate + 3-phosphoshikimate
?
show the reaction diagram
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-
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-
?
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
?
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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
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
slightly activating
CaCl2
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stimulation at 20 mM, inhibition above 100 mM
Cs+
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slightly activating
Li+
123.1% activity at 100 mM
MgCl2
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stimulation at 20 mM, inhibition above 100 mM
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
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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
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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
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competitive vs. phosphoenolpyruvate at saturated shikimate 3-phosphate concentration and vice versa
3-Bromopyruvate
5-Deoxy-shikimate 3-phosphate
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competitive vs. shikimate 3-phosphate
5-enolpyruvylshikimate 3-phosphate
ammonium heptamolybdate
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1.1 mM, 50% inhibition, no inhibition below 0.1 mM
Br-
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inhibition above 200 mM, stimulation below
Ca2+
90.1% residual activity at 1 mM
CaCl2
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above 100 mM
Carboxyallenyl phosphate
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strong
Cl-
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inhibition above 400 mM, stimulation below
Co3+
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10 mM, 25% inhibition
diethyldicarbonate
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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-
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inhibition above 100 mM, stimulation below
La3+
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10 mM, complete inhibition
MgCl2
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above 100 mM
molybdate
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10 mM, complete inhibition
N-ethylmaleimide
N-phosphonomethylglycine
NH4Cl
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inhibition above 300 mM, stimulation below
NO3-
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inhibition above 150 mM, stimulation below
Phenylglyoxal
phosphoenolpyruvate
pyruvate
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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
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shikimate 3-phosphate
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product inhibition
shikimate 3-phosphate-5-carboxymethyl-(2R)-phosphonate
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competitive vs. 5-enolpyruvylshikimate-3-phosphate and phosphate
shikimate 3-phosphate-5-carboxymethyl-(2S)-phosphonate
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competitive vs. 5-enolpyruvylshikimate-3-phosphate and phosphate
SO42-
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inhibition above 50 mM, slight stimulation below
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Br-
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stimulation at low concentrations, inhibition above 200 mM
I-
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stimulation at low concentrations, inhibition above 100 mM
NH4Cl
SO42-
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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
0.0018 - 43.6
phosphoenolpyruvate
0.02 - 0.43
shikimate 3-phosphate
additional information
additional information
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