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Literature summary extracted from

  • Hamed, R.B.; Gomez-Castellanos, J.R.; Thalhammer, A.; Harding, D.; Ducho, C.; Claridge, T.D.; Schofield. C.J.
    Stereoselective C-C bond formation catalysed by engineered carboxymethylproline synthases (2011), Nat. Chem., 3, 365-371.
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
2.3.1.226 H229A forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 75:25 compared to wild-type ratio of 55:45 Pectobacterium carotovorum
2.3.1.226 M108A forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 45:55 compared to wild-type ratio of 55:45 Pectobacterium carotovorum
2.3.1.226 M108I forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 92:8 compared to wild-type ratio of 55:45 Pectobacterium carotovorum
2.3.1.226 M108L forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 47:53 compared to wild-type ratio of 55:45. Forms the C6 epimers (6R):(6S) of (2S,5S)-6-ethyl-5-carboxymethylproline in the ratio of 72:18 compared to wild-type ratio of 65:35. Forms the C7 epimers (7R):(7S) of 7-methyl-(2S,6S)-carboxymethylpipecolic acid in the ratio of 60:40 compared to the wild-type ration of 66:34 Pectobacterium carotovorum
2.3.1.226 M108V forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 95:5 compared to wild-type ratio of 55:45 Pectobacterium carotovorum
2.3.1.226 Q111N forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 70:30 compared to wild-type ratio of 55:45 Pectobacterium carotovorum
2.3.1.226 W79A forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 16:84 compared to wild-type ratio of 55:45. Forms the C6 epimers (6R):(6S) of (2S,5S)-6-ethyl-5-carboxymethylproline in the ratio of 12:88 compared to wild-type ratio of 65:35. Forms the C7 epimers (7R):(7S) of 7-methyl-(2S,6S)-carboxymethylpipecolic acid in the ratio of 1:99 compared to the wild-type ration of 66:34 Pectobacterium carotovorum
2.3.1.226 W79F forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 17:83 compared to wild-type ratio of 55:45. Forms the C6 epimers (6R):(6S) of (2S,5S)-6-ethyl-5-carboxymethylproline in the ratio of 32:68 compared to wild-type ratio of 65:35. Forms the C7 epimers (7R):(7S) of 7-methyl-(2S,6S)-carboxymethylpipecolic acid in the ratio of : compared to the wild-type ration of 17:83 Pectobacterium carotovorum
2.3.1.226 W79F/M108A forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 11:89 compared to wild-type ratio of 55:45. Forms the C6 epimers (6R):(6S) of (2S,5S)-6-ethyl-5-carboxymethylproline in the ratio of 17:83 compared to wild-type ratio of 65:35. Forms the C7 epimers (7R):(7S) of 7-methyl-(2S,6S)-carboxymethylpipecolic acid in the ratio of 5:95 compared to the wild-type ration of 66:34 Pectobacterium carotovorum
2.3.1.226 W79F/M108V forms the C6 epimers (6R):(6S) of (2S,5S)-6-methyl-5-carboxymethylproline in the ratio of 56:44 compared to wild-type ratio of 55:45. Forms the C6 epimers (6R):(6S) of (2S,5S)-6-ethyl-5-carboxymethylproline in the ratio of 34:66 compared to wild-type ratio of 65:35. Forms the C7 epimers (7R):(7S) of 7-methyl-(2S,6S)-carboxymethylpipecolic acid in the ratio of 24:76 compared to the wild-type ration of 66:34 Pectobacterium carotovorum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.226 malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O Pectobacterium carotovorum
-
 CoA + (2S,5S)-5-carboxymethylproline + CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.226 Pectobacterium carotovorum
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.226 ethylmalonyl-CoA + (2S,5S)-carboxymethylproline + CO2 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 Pectobacterium carotovorum CoA + (2S,5S,6R)-6-ethyl-5-carboxymethylproline wild-type enzyme produces a 65:35 mixture of (6R)- and (6S)-epimer ?
2.3.1.226 ethylmalonyl-CoA + (2S,5S)-carboxymethylproline + CO2 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 Pectobacterium carotovorum CoA + (2S,5S,6S)-6-ethyl-5-carboxymethylproline wild-type enzyme produces a 65:35 mixture of (6R)- and (6S)-epimer ?
2.3.1.226 ethylmalonyl-CoA + L-2-aminoadipate semialdehyde activity with mutant enzymes W79F, W79F/M108A and W79F/M108V. mutant W79A: epimeric ethylmalonyl–CoA produces solely (2S,6S,7S)-(2S,6S)-carboxymethylpipecolic acid via reaction of (2R)-ethylmalonyl-CoA, whereas incubation of (2S)-ethylmalonyl–CoA and L-2-aminoadipate semialdehyde results in no detectable production of 7-ethyl-(2S,6S)-carboxymethylpipecolic acid Pectobacterium carotovorum CoA + (2S,6S,7R)-7-ethyl-carboxymethylpipecolic acid
-
 ?
2.3.1.226 ethylmalonyl-CoA + L-2-aminoadipate semialdehyde activity with mutant enzymes W79F, W79F/M108A and W79F/M108V. mutant W79A: epimeric ethylmalonyl–CoA produces solely (2S,6S,7S)-(2S,6S)-carboxymethylpipecolic acid via reaction of (2R)-ethylmalonyl-CoA, whereas incubation of (2S)-ethylmalonyl–CoA and L-2-aminoadipate semialdehyde results in no detectable production of 7-ethyl-(2S,6S)-carboxymethylpipecolic acid Pectobacterium carotovorum CoA + (2S,6S,7S)-7-ethyl-carboxymethylpipecolic acid
-
 ?
2.3.1.226 malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O
-
 Pectobacterium carotovorum CoA + (2S,5S)-5-carboxymethylproline + CO2
-
 ?
2.3.1.226 malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O the substrate is an equilibrium mixture of L-glutamate semialdehyde, 5-hydroxy-L-proline and L-pyrroline-5-carboxylate Pectobacterium carotovorum CoA + (2S,5S)-5-carboxymethylproline + CO2
-
 ?
2.3.1.226 methylmalonyl-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 Pectobacterium carotovorum CoA + (2S,5S,6R)-6-methyl-5-carboxymethylproline wild-type enzyme produces a 55:45 mixture of (6R)- and (6S)-epimer ?
2.3.1.226 methylmalonyl-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 Pectobacterium carotovorum CoA + (2S,5S,6S)-6-methyl-5-carboxymethylproline wild-type enzyme produces a 55:45 mixture of (6R)- and (6S)-epimer ?
2.3.1.226 methylmalonyl-CoA + L-2-aminoadipate semialdehyde
-
 Pectobacterium carotovorum CoA + (2S,6S,7R)-7-methyl-carboxymethylpipecolic acid wild-type enzyme produces a 66:34 mixture of (7R)- and (7S)-epimer ?
2.3.1.226 methylmalonyl-CoA + L-2-aminoadipate semialdehyde
-
 Pectobacterium carotovorum CoA + (2S,6S,7S)-7-methyl-carboxymethylpipecolic acid wild-type enzyme produces a 66:34 mixture of (7R)- and (7S)-epimer ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.226 CarB
-
 Pectobacterium carotovorum