Literature summary for 2.5.1.19 extracted from

Priestman, M.A.; Healy, M.L.; Becker, A.; Alberg, D.G.; Bartlett, P.A.; Lushington, G.H.; Schonbrunn, E.
Interaction of phosphonate analogues of the tetrahedral reaction intermediate with 5-enolpyruvylshikimate-3-phosphate synthase in atomic detail (2005), Biochemistry, 44, 3241-3248.

Application

Application	Comment	Organism
synthesis	enzyme is a target for development and synthesis of antimicrobial drugs	Escherichia coli

Cloned(Commentary)

Cloned (Comment)	Organism
overexpression in Escherichia coli	Escherichia coli

Crystallization (Commentary)

Crystallization (Comment)	Organism
enzyme complexed with inhibitor (3R,4S,5R)-5-((S)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid or with inhibitor (3R,4S,5R)-5-((R)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid, 100 mg/ml recombinant enzyme in 2.5 M sodium formate with 10 mM inhibitor, hanging drop vapour diffusion method, 19°C, X-ray diffraction at -180°C using the rotation method on single flash-frozen crystals, structure determination and analysis at 1.5 and 1.9 A resolution, respectively	Escherichia coli

Crystallization (Comment)

Organism

enzyme complexed with inhibitor (3R,4S,5R)-5-((S)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid or with inhibitor (3R,4S,5R)-5-((R)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid, 100 mg/ml recombinant enzyme in 2.5 M sodium formate with 10 mM inhibitor, hanging drop vapour diffusion method, 19°C, X-ray diffraction at -180°C using the rotation method on single flash-frozen crystals, structure determination and analysis at 1.5 and 1.9 A resolution, respectively

Escherichia coli

Inhibitors

Inhibitors	Comment	Organism
(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	Escherichia coli
(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	Escherichia coli
glyphosate	-	Escherichia coli

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
additional information	-	additional information	stopped-flow kinetics	Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
phosphoenolpyruvate + 3-phosphoshikimate	Escherichia coli	penultimate step in the shikimate pathway	phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate	-	?

Organism

Organism	UniProt	Comment	Textmining
Escherichia coli	P0A6D3	-	-

Reaction

Reaction	Comment	Organism	Reaction ID
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate	catalytic mechanism, tetrahedral reaction intermediate, catalytic cycle of the enzyme, overview	Escherichia coli	a

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
phosphoenolpyruvate + 3-phosphoshikimate	-	Escherichia coli	phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate	-	?
phosphoenolpyruvate + 3-phosphoshikimate	penultimate step in the shikimate pathway	Escherichia coli	phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate	-	?

Synonyms

Synonyms	Comment	Organism
5-enolpyruvylshikimate-3-phosphate synthase	-	Escherichia coli
EPSPS	-	Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
20	-	assay at	Escherichia coli

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7	-	assay at	Escherichia coli

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism
additional information	-	additional information	-	Escherichia coli
0.000016	-	(3R,4S,5R)-5-((R)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid	versus 3-phosphoshikimate	Escherichia coli
0.00075	-	(3R,4S,5R)-5-((S)-1-carboxy-1-phosphono-ethoxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid	versus 3-phosphoshikimate	Escherichia coli