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2.5.1.19: 3-phosphoshikimate 1-carboxyvinyltransferase

This is an abbreviated version!
For detailed information about 3-phosphoshikimate 1-carboxyvinyltransferase, go to the full flat file.

Word Map on EC 2.5.1.19

Reaction

phosphoenolpyruvate
+
3-phosphoshikimate
=
phosphate
 +
5-O-(1-carboxyvinyl)-3-phosphoshikimate

Synonyms

3-enolpyruvylshikimate 5-phosphate synthase, 3-enolpyruvylshikimic acid-5-phosphate synthetase, 3-phosphoshikimate 1-carboxyvinyl-transferase, 3-phosphoshikimate 1-carboxyvinyltransferase, 3-phosphoshikimate-1-carboxyvinyl-transferase, 5'-enolpyruvylshikimate-3-phosphate synthase, 5-enol pyruvylshikimate 3-phosphate synthase, 5-enol-pyruvyl-shikimate-3-phosphate synthase, 5-enol-pyruvylshikimate 3-phosphate synthase, 5-enol-pyruvylshikimate-3-phosphate synthase, 5-enolpyruvyl-3-phosphoshikimate synthase, 5-enolpyruvylshikimate 3-phosphate synthase, 5-enolpyruvylshikimate-3-phosphate synthase, 5-enolpyruvylshikimate-3-phosphate synthetase, 5-enolpyruvylshikimate-3-phosphoric acid synthase, 5-enolpyruvylshikimate-3phosphate synthase, 5-enolpyruvylshikimic acid-3-phosphate synthase, 5-enopyruvylshikimate-3-phosphate synthase, 5-enoylpyruvylshikimate 3-phosphate synthase, 5-enoylpyruvylshikimate-3-phosphate synthase, A1501 EPSPS, AM79, AroA, AroA(1398), AroA(A1501), AroA1398, CaEPSPS, cp4 epsps, DsaroA, Dunaliella salina 5-enolpyruvylshikimate-3-phosphate synthase, Dunaliella salina EPSP synthase, E. coli EPSPS, EcaroA, enolpyruvylshikimate 3-phosphate synthase, enolpyruvylshikimate phosphate synthase, enolpyruvylshikimate-3-phosphate synthase, EPSP synhthase, EPSP synthase, EPSPS, G2 5-enolpyruvyl shikimate 3-phosphate synthase, G2 EPSPS, GR79Ms, maize EPSP synthase, maize EPSPS, mEPSPS, More, Mt EPSPS, Mycobacterium tuberculosis 5-enolpyruvylshikimate-3-phosphate synthase, Potri.002G146400, StaroA, synthase, 5-enolpyruvoylshikimate 3-phosphate

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.19 3-phosphoshikimate 1-carboxyvinyltransferase

Inhibitors

Inhibitors on EC 2.5.1.19 - 3-phosphoshikimate 1-carboxyvinyltransferase

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INHIBITOR
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
ammonium heptamolybdate
-
1.1 mM, 50% inhibition, no inhibition below 0.1 mM
Br-
-
inhibition above 200 mM, stimulation below
Ca2+
90.1% residual activity at 1 mM
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
-