2.2.1.9: 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic-acid synthase
This is an abbreviated version!
For detailed information about 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic-acid synthase, go to the full flat file.
Word Map on EC 2.2.1.9
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2.2.1.9
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menaquinone
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thiamin
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thdp-dependent
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diphosphate-dependent
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alpha-ketoglutarate
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2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic
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dioxide
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benzoylformate
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decarboxylases
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stereoselective
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hydrolases
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alpha/beta
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o-succinylbenzoic
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metal-ion-dependent
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three-domain
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two-stage
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medium-resolution
- 2.2.1.9
- menaquinone
- thiamin
-
thdp-dependent
-
diphosphate-dependent
- alpha-ketoglutarate
-
2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic
- dioxide
- benzoylformate
- decarboxylases
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stereoselective
- hydrolases
- alpha/beta
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o-succinylbenzoic
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metal-ion-dependent
-
three-domain
-
two-stage
-
medium-resolution
Reaction
Synonyms
(1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase, (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate synthase, 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexadiene-1-carboxylate synthase, 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase, 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid synthase, EC 2.5.1.64, EcMenD, MenD, Rv0555, SEPHCHC synthase, SHCHC synthase
ECTree
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Substrates Products
Substrates Products on EC 2.2.1.9 - 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic-acid synthase
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REACTION DIAGRAM
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid + 2-oxoglutarate
? + CO2
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analogue of isochorismate, weaker binding to enzyme. Only the (+)-enantiomer is a substrate
-
-
?
(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate + 2-oxoglutarate
(1R,2S,5S,6S)-2-succinyl-5,6-dihydroxycyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylate + 2-oxoglutarate
2-succinyl-6-amino-5-hydroxycyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
2,3-dihydroxybenzaldehyde + 2-oxoglutarate
(5R)-5-(2,3-dihydroxyphenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
2-bromobenzaldehyde + 2-oxoglutarate
(5R)-5-(2-bromophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
2-chlorobenzaldehyde + 2-oxoglutarate
(5R)-5-(2-chlorophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
2-fluorobenzaldehyde + 2-oxoglutarate
(5R)-5-(2-fluorophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
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-
?
2-fluorobenzaldehyde + oxaloacetate
(1R)-1-(2-fluorophenyl)-1-hydroxypropan-2-one + 2 CO2
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assay at pH 8
-
-
?
2-fluorobenzaldehyde + pyruvate
(1R)-1-(2-fluorophenyl)-1-hydroxypropan-2-one + CO2
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assay at pH 8
-
-
?
2-iodobenzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-5-(2-iodophenyl)-4-oxopentanoic acid + CO2
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assay at pH 8
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-
?
2-methylbenzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-5-(2-methylphenyl)-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
3,4-dihydroxybenzaldehyde + 2-oxoglutarate
(5R)-5-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
3-fluorobenzaldehyde + 2-oxoglutarate
(5R)-5-(3-fluorophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
-
assay at pH 8
-
-
?
3-iodobenzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-5-(3-iodophenyl)-4-oxopentanoic acid + CO2
-
assay at pH 8
-
-
?
3-methoxybenzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-5-(3-methoxyphenyl)-4-oxopentanoic acid + CO2
-
assay at pH 8
-
-
?
4-chlorbenzaldehyde + 2-oxoglutarate
(5R)-5-(4-chlorophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
4-fluorobenzaldehyde + 2-oxoglutarate
(5R)-5-(4-fluorophenyl)-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
4-hydroxybenzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-5-(4-hydroxyphenyl)-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
acetaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-4-oxohexanoic acid + CO2
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assay at pH 8
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-
?
benzaldehyde + 2-oxoglutarate
(5R)-5-hydroxy-4-oxo-5-phenylpentanoic acid + CO2
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assay at pH 8
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-
?
benzaldehyde + oxaloacetate
(1R)-1-hydroxy-1-phenylpropan-2-one + 2 CO2
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assay at pH 8
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-
?
benzaldehyde + pyruvate
(1R)-1-hydroxy-1-phenylpropan-2-one + 2 CO2
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assay at pH 8
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-
?
cyclohex-1-ene-1-carbaldehyde + 2-oxoglutarate
(5R)-5-cyclohex-1-en-1-yl-5-hydroxy-4-oxopentanoic acid + CO2
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assay at pH 8
-
-
?
glyoxylate + 2-oxoglutarate
5-hydroxy-4-oxopentanoic acid + 2 CO2
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assay at pH 8
-
-
?
hexanal + 2-oxoglutarate
(5R)-5-hydroxy-4-oxodecanoic acid + CO2
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assay at pH 8
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-
?
isochorismate + 2-oxoglutarate
(1R,2S,5S,6S)-5-[(1-carboxyethenyl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid + CO2
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate + CO2
pyruvate + 2-oxoglutarate
4-hydroxy-5-oxohexanoic acid + 2 CO2
-
assay at pH 8
-
-
?
undec-10-enal + 2-oxoglutarate
(5R)-5-hydroxy-4-oxopentadec-14-enoic acid + CO2
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assay at pH 8
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-
?
additional information
?
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MenD participates in the menaquinone (vitamin K2) biosynthetic pathway
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-
?
(1R,2S,5S,6S)-5-[(1-carboxyethenyl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid + CO2
-
assay at pH 8
-
-
?
isochorismate + 2-oxoglutarate
(1R,2S,5S,6S)-5-[(1-carboxyethenyl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid + CO2
-
-
-
-
?
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
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the enzyme is involved in biosynthesis of vitamin K2 (menoquinone). Under basic conditions, the product can spontaneously lose pyruvate to form (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
under basic conditions, the product can spontaneously lose pyruvate to form (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
5-enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate + CO2
-
-
-
?
isochorismate + 2-oxoglutarate
5-enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate + CO2
via a tetrahedral enamine/acyl anion intermediate, overview
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-
?