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Information on EC 2.5.1.19 - 3-phosphoshikimate 1-carboxyvinyltransferase
for references in articles please use BRENDA:EC2.5.1.19
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EC Tree 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
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 2.5.1.19
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excitatory
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postsynaptic
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depolarization
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ipsps
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afferent
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monosynaptic
- hippocampal
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pyramidal
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presynaptic
- synapses
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latency
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fire
- nmda
- motoneuron
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interneurons
- glyphosate
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firing
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hyperpolarization
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electrophysiological
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antidromic
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summation
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subthreshold
- bicuculline
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gabaa
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disynaptic
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non-nmda
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tetanic
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6-cyano-7-nitroquinoxaline-2,3-dione
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volley
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schaffer
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quantal
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unitary
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paired-pulse
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orthodromic
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glyphosate-resistant
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short-latency
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thalamocortical
- biotechnology
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electrotonic
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reticulospinal
- radiatum
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homonymous
- drug development
- agriculture
- synthesis
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interstimulus
-
funiculus
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suprathreshold
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preganglionic
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low-threshold
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impale
-
decerebrate
- biocytin
-
afterhyperpolarization
Reaction Schemes
showSynonyms
epsps, 5-enolpyruvylshikimate-3-phosphate synthase, epsp synthase, cp4 epsps, mepsps, 5-enolpyruvylshikimate 3-phosphate synthase, 5-enol-pyruvylshikimate-3-phosphate synthase, 5-enol-pyruvyl-shikimate-3-phosphate synthase, caepsps, 3-phosphoshikimate 1-carboxyvinyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-enolpyruvylshikimate 5-phosphate synthase
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3-enolpyruvylshikimic acid-5-phosphate synthetase
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3-phosphoshikimate 1-carboxyvinyl-transferase
3-phosphoshikimate-1-carboxyvinyl-transferase
5'-enolpyruvylshikimate-3-phosphate synthase
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5-enol-pyruvyl-shikimate-3-phosphate synthase
5-enol-pyruvylshikimate 3-phosphate synthase
5-enol-pyruvylshikimate-3-phosphate synthase
5-enolpyruvyl-3-phosphoshikimate synthase
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5-enolpyruvylshikimate 3-phosphate synthase
5-enolpyruvylshikimate-3-phosphate synthase
5-enolpyruvylshikimate-3-phosphate synthetase
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5-enolpyruvylshikimate-3-phosphoric acid synthase
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5-enolpyruvylshikimate-3phosphate synthase
5-enolpyruvylshikimic acid-3-phosphate synthase
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5-enopyruvylshikimate-3-phosphate synthase
5-enoylpyruvylshikimate 3-phosphate synthase
A1501 EPSPS
AroA
AroA(1398)
AroA(A1501)
AroA1398
DsaroA
Dunaliella salina 5-enolpyruvylshikimate-3-phosphate synthase
Dunaliella salina EPSP synthase
enolpyruvylshikimate phosphate synthase
enolpyruvylshikimate-3-phosphate synthase
EPSP synhthase
EPSP synthase
EPSPS
G2 5-enolpyruvyl shikimate 3-phosphate synthase
G2 EPSPS
Mt EPSPS
Mycobacterium tuberculosis 5-enolpyruvylshikimate-3-phosphate synthase
synthase, 5-enolpyruvoylshikimate 3-phosphate
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additional information
5-enol-pyruvyl-shikimate-3-phosphate synthase
Limnospira fusiformis Hegewald 1976/83
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5-enolpyruvylshikimate 3-phosphate synthase
class II, glyphosate-tolerant
5-enolpyruvylshikimate 3-phosphate synthase
class II, glyphosate-tolerant
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5-enolpyruvylshikimate 3-phosphate synthase
class I, glyphosate-sensitive
5-enolpyruvylshikimate 3-phosphate synthase
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class II, glyphosate-tolerant
5-enolpyruvylshikimate-3-phosphate synthase
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5-enolpyruvylshikimate-3-phosphate synthase
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5-enolpyruvylshikimate-3-phosphate synthase
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5-enolpyruvylshikimate-3phosphate synthase
Bacteria ATX1398
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AroA(1398)
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glyphosate-tolerant gene product from strain ATX1398 that lacks protein sequence hallmarks of class II EPSP synthases
AroA(1398)
Bacteria ATX1398
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glyphosate-tolerant gene product from strain ATX1398 that lacks protein sequence hallmarks of class II EPSP synthases
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AroA1398
Bacteria ATX1398
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enolpyruvylshikimate phosphate synthase
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enolpyruvylshikimate phosphate synthase
Bacteria ATX1398
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EPSP synthase
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EPSP synthase
Bacteria ATX1398
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EPSP synthase
Limnospira fusiformis Hegewald 1976/83
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G2 5-enolpyruvyl shikimate 3-phosphate synthase
glyphosate resistant
G2 5-enolpyruvyl shikimate 3-phosphate synthase
glyphosate resistant
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Mycobacterium tuberculosis 5-enolpyruvylshikimate-3-phosphate synthase
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Mycobacterium tuberculosis 5-enolpyruvylshikimate-3-phosphate synthase
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additional information
enzyme belongs to the family of enolpyruvyl transferases
additional information
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class II 5-enolpyruvylshikimate-3-phosphate synthases are less sensitive to glyphosate in contrary to class I 5-enolpyruvylshikimate-3-phosphate synthases which are highly sensitive to inhibition with glyphosate
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
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phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
proposed mechanism
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phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
binding of shikimate 3-phosphate leads to a saturable and stable conformational change in the isolated N-terminal domain
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
catalytic mechanism, tetrahedral reaction intermediate, active site structure, wild-type and mutant D313A
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
catalytic mechanism, tetrahedral reaction intermediate, catalytic cycle of the enzyme, overview
phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
enolpyruvylshikimate 3-phosphate ketal is catalytically formed as side product upon enolpyruvyl activation through protonation by an intramolecular nucleophilic addition of O4 to C2 of the enolpyruvyl moiety
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phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
ordered substrate binding with 3-phosphoshikimate being bound first
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phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
via formation of a tetrahedral intermediate (TI) after which residue His385 is in a neutral form while residues Lys22, Lys340 and Lys411 are protonated, Asp313 mediates attack of the TI C4-OH group (as oxyanion, shikimate-3-phosphate moiety) at the TI C3-methyl group (phosphoenolpyruvate moiety), Lys22 serves as general acid catalyst for TI breakdown
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
enolpyruvate group transfer
enolpyruvate group transfer
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enolpyruvate group transfer
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induced-fit mechanism, formation of a 2-(S) configured tetrahedral reaction intermediate by covalent linkage of the two substrates
enolpyruvate group transfer
induced-fit mechanism, formation of a 2-(S) configured tetrahedral reaction intermediate by covalent linkage of the two substrates
enolpyruvate group transfer
induced-fit mechanism, formation of a 2-(S) configured tetrahedral reaction intermediate by covalent linkage of the two substrates
enolpyruvate group transfer
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induced-fit mechanism, formation of a 2-(S) configured tetrahedral reaction intermediate by covalent linkage of the two substrates
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
chorismate biosynthesis from 3-dehydroquinate
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SYSTEMATIC NAME
IUBMB Comments
phosphoenolpyruvate:3-phosphoshikimate 5-O-(1-carboxyvinyl)-transferase
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CAS REGISTRY NUMBER
COMMENTARY
9068-73-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5-enolpyruvylshikimate 3-phosphate + H2O
5-enolpyruvylshikimate 3-phosphate ketal
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Substrates: enzymatic hydrolysis, pH 7.0, 25°C, in presence of phosphate scavenging system and excess of enzyme
Products: -
Products: -
?
phosphate + 5-enolpyruvylshikimate 3-phosphate
shikimate 3-phosphate + phosphoenolpyruvate
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Substrates: reverse reaction
Products: phosphoenolpyruvate generation coupled to pyruvate kinase and lactate dehydrogenase and monitored spectrophotometrically at 340 nm, pH7.0, in presence of ADP, NADH, MgCl2
Products: 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
?
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
shikimate 3-phosphate + phosphoenolpyruvate
phosphate + 5-enolpyruvylshikimate 3-phosphate
shikimate 3-phosphate + phosphoenolpyruvate
phosphate + 5-enpolpyruvylshikimate 3-phosphate
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: -
Products: -
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
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Substrates: involved in aromatic acid biosynthesis
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: part of shikimate pathway
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: involved in aromatic acid biosynthesis
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: critical enzyme in the shikimate pathway
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: sixth enzyme in the shikimate pathway. The enzyme is widely involved in glyphosate tolerant transgenic plants because it is the primary target of the nonselective herbicide lyphosate
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: sixth enzyme in the shikimate pathway. The enzyme is widely involved in glyphosate tolerant transgenic plants because it is the primary target of the nonselective herbicide lyphosate
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: -
Products: -
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: -
Products: -
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: transfers enolpyruvate group from phosphoenolpyruvate to 5-hydroxyl group of 3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: sixth reaction of chorismate pathway
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: part of shikimate pathway
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: involved in chorismate biosynthesis
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: involved in aromatic acid biosynthesis
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: part of shikimate pathway
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Products: i.e. 5-O-(1-carboxyvinyl)-3-phosphoshikimate
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
Substrates: -
Products: -
Products: -
?
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: -
Products: -
r
phosphoenolpyruvate + 3-phosphoshikimate
phosphate + 5-enolpyruvylshikimate 3-phosphate
-
Substrates: -
Products: i.e. 5-O-(1-carboxy
Products: i.e. 5-O-(1-carboxy