2.3.1.226: carboxymethylproline synthase
This is an abbreviated version!
For detailed information about carboxymethylproline synthase, go to the full flat file.
Word Map on EC 2.3.1.226
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2.3.1.226
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crotonase
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functionalised
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methylmalonyl-coa
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carbapenams
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beta-lactams
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synthesis
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carboxylase
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biocatalysis
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cyclization
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synthases
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bicyclic
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malonyl-coenzyme
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acetyl-coa
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crotonyl-coa
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simplest
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stereoselective
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medicine
- 2.3.1.226
- crotonase
-
functionalised
- methylmalonyl-coa
-
carbapenams
- beta-lactams
- synthesis
- carboxylase
-
biocatalysis
-
cyclization
- synthases
-
bicyclic
-
malonyl-coenzyme
- acetyl-coa
- crotonyl-coa
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simplest
-
stereoselective
- medicine
Reaction
Synonyms
CarB
ECTree
2.3.1.226 carboxymethylproline synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.3.1.226 - carboxymethylproline synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
ethylmalonyl-CoA + (2S,5S)-carboxymethylproline + CO2
CoA + (2S,5S,6R)-6-ethyl-5-carboxymethylproline
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the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate. Some of the CarB variants catalyse the production of the two C6 epimers of (2S,5S)-6-ethyl-5-carboxymethylproline
wild-type enzyme produces a 65:35 mixture of (6R)- and (6S)-epimer
-
?
ethylmalonyl-CoA + (2S,5S)-carboxymethylproline + CO2
CoA + (2S,5S,6S)-6-ethyl-5-carboxymethylproline
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the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate. Some of the CarB variants catalyse the production of the two C6 epimers of (2S,5S)-6-ethyl-5-carboxymethylproline
wild-type enzyme produces a 65:35 mixture of (6R)- and (6S)-epimer
-
?
ethylmalonyl-CoA + L-2-aminoadipate semialdehyde
CoA + (2S,6S,7R)-7-ethyl-carboxymethylpipecolic acid
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activity with mutant enzymes W79F, W79F/M108A and W79F/M108V. mutant W79A: epimeric ethylmalonylCoA produces solely (2S,6S,7S)-(2S,6S)-carboxymethylpipecolic acid via reaction of (2R)-ethylmalonyl-CoA, whereas incubation of (2S)-ethylmalonylCoA and L-2-aminoadipate semialdehyde results in no detectable production of 7-ethyl-(2S,6S)-carboxymethylpipecolic acid
-
-
?
ethylmalonyl-CoA + L-2-aminoadipate semialdehyde
CoA + (2S,6S,7S)-7-ethyl-carboxymethylpipecolic acid
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activity with mutant enzymes W79F, W79F/M108A and W79F/M108V. mutant W79A: epimeric ethylmalonylCoA produces solely (2S,6S,7S)-(2S,6S)-carboxymethylpipecolic acid via reaction of (2R)-ethylmalonyl-CoA, whereas incubation of (2S)-ethylmalonylCoA and L-2-aminoadipate semialdehyde results in no detectable production of 7-ethyl-(2S,6S)-carboxymethylpipecolic acid
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-carboxymethylproline + CO2
malonyl-CoA + L-2-aminopimelate semialdehyde
CoA + (2S,7S)-7-(carboxymethyl)-azepane-2-carboxylic acid + CO2
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the CarB His229Ala variant is able to form the target compound in a yield of about 3 times higher than that obtained with wild-type CarB
-
-
?
methylmalonyl-CoA + (2S,5S)-5-carboxymethylproline + CO2
CoA + (2S,5S,6R)-6-methyl-5-carboxymethylproline
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the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate
wild-type enzyme produces a 55:45 mixture of (6R)- and (6S)-epimer
-
?
methylmalonyl-CoA + (2S,5S)-5-carboxymethylproline + CO2
CoA + (2S,5S,6S)-6-methyl-5-carboxymethylproline
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the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate
wild-type enzyme produces a 55:45 mixture of (6R)- and (6S)-epimer
-
?
methylmalonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-6-methyl-5-carboxymethylproline + CO2
-
-
-
-
?
methylmalonyl-CoA + L-2-aminoadipate semialdehyde
CoA + (2S,6S,7R)-7-methyl-carboxymethylpipecolic acid
-
-
wild-type enzyme produces a 66:34 mixture of (7R)- and (7S)-epimer
-
?
methylmalonyl-CoA + L-2-aminoadipate semialdehyde
CoA + (2S,6S,7S)-7-methyl-carboxymethylpipecolic acid
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-
wild-type enzyme produces a 66:34 mixture of (7R)- and (7S)-epimer
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
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the enzyme catalyzes committed step in the biosynthesis of (5R)-carbapenem-3-carboxylic acid, the simplest of the medicinally important carbapenem antibiotics
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-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
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acetyl-CoA is not a substrate
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-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
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CarB is a member of the crotonase superfamily of enzymes. In addition to decarboxylation and thioester hydrolysis steps, it catalyzes C-C bond formation leading to a substituted heterocycle. Mechanistic studies show that C-C bond formation by CarB most probably occurs by reaction of P5C with an oxy-anion stabilized enolate, and thioester hydrolysis most probably proceeds by direct attack of an activated water molecule
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-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-carboxymethylproline + CO2
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the enzyme is involved in the biosynthesis of 1-carbapen-2-em-3-carboxylic acid, a simple beta-lactam antibiotic
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-
?
malonyl-CoA + L-glutamate-gamma-semialdehyde
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + L-glutamate-gamma-semialdehyde
CoA + (2S,5S)-5-carboxymethylproline + CO2
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L-glutamate-gamma-semialdehyde but not D-glutamate-gamma-semialdehyde is a substrate of the enzyme
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-
?
additional information
?
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CarB catalyzes the independent decarboxylation of malonyl-CoA and methylmalonyl-CoA and the hydrolysis of CoA esters such as acetyl-CoA and propionyl-CoA
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-
?
additional information
?
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no activity with L-2-aminosuberate semialdehyde (wild-type enzyme and mutant enzyme H229A)
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-
?
