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Literature summary extracted from
- Mechanistic, mutational, and structural evaluation of a taxus phenylalanine aminomutase (2011), Biochemistry, 50, 2919-2930.
Activating Compound
| EC Number | Activating Compound | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.4.3.10 | 4-methylidene-1H-imidazol-5(4H)-one | - |
Taxus canadensis |  |
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 5.4.3.10 | expression in Escherichia coli | Taxus canadensis |
Crystallization (Commentary)
| EC Number | Crystallization (Comment) | Organism |
|---|---|---|
| 5.4.3.10 | to 2.38 A resolution, space group C2. A (E)-cinnamate molecule is bound in the active site, lying above the 4-methylidene-1H-imidazol-5(4H)-one cofactor and under a loop region that includes residues 80-97, which define the top of the active site. The (E)-cinnamate molecule lies about 3.4 A above the methylidene carbon of the 4-methylidene-1H-imidazol-5(4H)-one moiety. The carboxylate of the cinnamate makes a salt bridge interaction with a strongly conserved residue R325, which serves to position the product in the active site. The plane of the aromatic ring of the cinnamate is displaced about 20° from the perpendicular relative to the pi-bond plane of the propenoate carboncarbon double bond. The aromatic ring is bound relatively loosely in the active site, making only one direct hydrophobic interaction with residue L104 | Taxus canadensis |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 5.4.3.10 | L104A | 1.5-fold increase in kcat and a decrease in KM values for 3'-methyl-alpha-phenylalanine and styryl-alpha-alanine substrates | Taxus canadensis |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.10 | 0.057 | - |
L-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.073 | - |
4'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.083 | - |
3'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.091 | - |
4'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.12 | - |
styryl-alpha-alanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.136 | - |
L-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.25 | - |
styryl-alpha-alanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.397 | - |
3'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 5.4.3.10 | Taxus canadensis | Q6GZ04 | - |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.3.10 | 3'-methyl-alpha-phenylalanine | - |
Taxus canadensis | 3'-methyl-beta-phenylalanine | plus 3'-methylcinnamate, product of ammonia lyase reaction. Distribution of 3'-methyl-beta-phenylalanine and 3'-methylcinnamate is at about 1:1 | ? | |
| 5.4.3.10 | 4'-methyl-alpha-phenylalanine | - |
Taxus canadensis | 4'-methyl-beta-phenylalanine | plus 4'-methylcinnamate, product of ammonia lyase reaction | ? | |
| 5.4.3.10 | L-phenylalanine | - |
Taxus canadensis | L-beta-phenylalanine | - |
? | |
| 5.4.3.10 | additional information | (E)-cinnamate is both a substrate and an intermediate of the reaction. To account for the distinct (3alpha)-beta-amino acid stereochemistry catalyzed by the enzyme, the cinnamate skeleton must rotate the C1-Calpha and Cipso-Cbeta bonds 180° in the active site prior to exchange and rebinding of theNH2/H pair to the cinnamate | Taxus canadensis | ? | - |
? | |
| 5.4.3.10 | styryl-alpha-alanine | - |
Taxus canadensis | 5-phenyl-(2E,4E)-pentadienoate | - |
? | |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.10 | 0.0002 | - |
styryl-alpha-alanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.003 | - |
L-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.003 | - |
styryl-alpha-alanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.02 | - |
4'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.022 | - |
3'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.028 | - |
3'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.03 | - |
4'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.053 | - |
L-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.10 | 0.022 | - |
L-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.025 | - |
styryl-alpha-alanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.055 | - |
3'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.27 | - |
4'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.33 | - |
4'-methyl-alpha-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.34 | - |
3'-methyl-alpha-phenylalanine | mutant L104A, pH 8.5, 31°C | Taxus canadensis | |
| 5.4.3.10 | 0.93 | - |
L-phenylalanine | wild-type, pH 8.5, 31°C | Taxus canadensis | |
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