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
-
2.3.1.226
-
crotonase
-
functionalised
-
methylmalonyl-coa
-
carbapenams
-
beta-lactams
-
synthesis
-
carboxylase
-
biocatalysis
-
cyclization
-
synthases
-
bicyclic
-
malonyl-coenzyme
-
acetyl-coa
-
crotonyl-coa
-
simplest
-
stereoselective
-
medicine
- 2.3.1.226
- crotonase
-
functionalised
- methylmalonyl-coa
-
carbapenams
- beta-lactams
- synthesis
- carboxylase
-
biocatalysis
-
cyclization
- synthases
-
bicyclic
-
malonyl-coenzyme
- acetyl-coa
- crotonyl-coa
-
simplest
-
stereoselective
- medicine
Reaction
Synonyms
CarB
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 2.3.1.226 - carboxymethylproline synthase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
REACTION DIAGRAM
ethylmalonyl-CoA + (2S,5S)-carboxymethylproline + CO2
CoA + (2S,5S,6R)-6-ethyl-5-carboxymethylproline
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
-
wild-type enzyme produces a 66:34 mixture of (7R)- and (7S)-epimer
-
?
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
-
the enzyme catalyzes committed step in the biosynthesis of (5R)-carbapenem-3-carboxylic acid, the simplest of the medicinally important carbapenem antibiotics
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
acetyl-CoA is not a substrate
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
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
-
-
?
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
-
-
-
-
?
CoA + (2S,5S)-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
CoA + (2S,5S)-carboxymethylproline + CO2
-
the enzyme is involved in the biosynthesis of 1-carbapen-2-em-3-carboxylic acid, a simple beta-lactam antibiotic
-
-
?
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
-
-
-
?
malonyl-CoA + L-glutamate-gamma-semialdehyde
CoA + (2S,5S)-5-carboxymethylproline + CO2
-
L-glutamate-gamma-semialdehyde but not D-glutamate-gamma-semialdehyde is a substrate of the enzyme
-
-
?
?
-
-
CarB catalyzes the independent decarboxylation of malonyl-CoA and methylmalonyl-CoA and the hydrolysis of CoA esters such as acetyl-CoA and propionyl-CoA
-
-
?
additional information
?
-
-
no activity with L-2-aminosuberate semialdehyde (wild-type enzyme and mutant enzyme H229A)
-
-
?