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Literature summary extracted from
- Ring-substituted beta-arylalanines for probing substituent effects on the isomerization reaction catalyzed by an aminomutase (2014), ACS Catal., 4, 3077-3090 .
No PubMed abstract available
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 5.4.3.11 | synthesis | utility of the methylidene imidazolone-dependent Pantoea agglomerans phenylalanine aminomutase (PaPAM) for making non-natural beta-amino acids, substrate specificity of PaPAM with several commercially available (S)-arylalanine substrates, overview | Pantoea agglomerans |
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 5.4.3.11 | gene papam, recombinant expression of C-terminally His6-tagged PaPAM in Escherichia coli strain BL21(DE3) | Pantoea agglomerans |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.11 | additional information | - |
additional information | Michaelis-Menten kinetics | Pantoea agglomerans | |
| 5.4.3.11 | 0.027 | - |
3-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans |  |
| 5.4.3.11 | 0.029 | - |
4-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.073 | - |
2-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.088 | - |
2-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.132 | - |
3-thiophen-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.163 | - |
4-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.164 | - |
2-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.168 | - |
L-phenylalanine | pH 8.0, 31°C | Pantoea agglomerans | |
| 5.4.3.11 | 0.204 | - |
3-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.337 | - |
3-thiophen-3-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.339 | - |
3-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.415 | - |
3-furan-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.43 | - |
3-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.432 | - |
3-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.491 | - |
4-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.525 | - |
4-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.752 | - |
4-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.99 | - |
3-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 1.187 | - |
4-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.3.11 | L-phenylalanine | Pantoea agglomerans | - |
D-beta-phenylalanine | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 5.4.3.11 | Pantoea agglomerans | Q84FL5 | i.e. Enterobacter agglomerans or Erwinia herbicola | - |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 5.4.3.11 | recombinant C-terminally His6-tagged PaPAM from Escherichia coli strain BL21(DE3) by nickel affinity chromatography, and ultrafiltration, to over 95% purity | Pantoea agglomerans |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 5.4.3.11 | L-phenylalanine = D-beta-phenylalanine | reaction mechanism, detailed overview. Proposed elimination mechanisms for the displacement of the NH2-MIO adduct. The final reaction sequence of the MIO-dependent aminomutases involves an alpha,beta-addition reaction, where the NH2-MIO and a proton add across the double bond of the acrylate intermediate. Alternatively, PaPAM can use a stepwise addition sequence where the nucleophile (NH2-MIO) couples to form a 1,4-Michael adduct. This conjugate addition route benefits from an electropositive (delta+) Cbeta by delocalizing the Pi-electrons toward the carboxylate of the substrate | Pantoea agglomerans |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.3.11 | 2-fluoro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(2-fluorophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 2-methoxy-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(2-methoxyphenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 2-methyl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(o-tolyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-bromo-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-bromophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-chloro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-chlorophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-fluoro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-fluorophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-furan-2-yl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(furan-2-yl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-methoxy-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-methoxyphenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-methyl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-methylphenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-nitro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(3-nitrophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-thiophen-2-yl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(thiophen-2-yl)propanoic acid | - |
? | |
| 5.4.3.11 | 3-thiophen-3-yl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(thiophen-3-yl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-bromo-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-bromophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-chloro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-chlorophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-fluoro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-fluorophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-methoxy-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-methoxyphenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-methyl-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-methylphenyl)propanoic acid | - |
? | |
| 5.4.3.11 | 4-nitro-L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-(4-nitrophenyl)propanoic acid | - |
? | |
| 5.4.3.11 | L-phenylalanine | - |
Pantoea agglomerans | D-beta-phenylalanine | - |
? | |
| 5.4.3.11 | L-phenylalanine | - |
Pantoea agglomerans | (S)-3-amino-3-phenylpropanoic acid | - |
? | |
| 5.4.3.11 | additional information | enzyme substrate specificity, detailed overview. Interactions the most significant are between the substrates and residues Phe428, Val108, Leu421, Leu104, Gln456, and Tyr. Electronic effects of ortho-, para-, and meta-substituents. The enzyme produces a different amount of cinnamate as side-product dependent on the substrate, e.g. the product pool catalyzed by PaPAM from 13 contains more cinnamate analogue (21.7%) compared to that made from other m-substituted substrates 3-bromo-L-phenylalanine, 3-chloro-L-phenylalanine, 3-nitro-L-phenylalanine, and 3-methoxy-L-phenylalanine that contain between 1.0% and 7.4%. Relationship between PaPAM-substrate interaction energies, flexibility, and Km. Compounds 2-bromo-L-phenylalanine, 2-chloro-L-phenylalanine, and 2-nitro-L-phenylalanine are no substrates | Pantoea agglomerans | ? | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 5.4.3.11 | ? | x * 59000, about, recombinant His-tagged enzyme, SDS-PAGE | Pantoea agglomerans |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 5.4.3.11 | admH | - |
Pantoea agglomerans |
| 5.4.3.11 | methylidene imidazolone-dependent phenylalanine aminomutase | - |
Pantoea agglomerans |
| 5.4.3.11 | MIO-dependent phenylalanine ammonia lyase | - |
Pantoea agglomerans |
| 5.4.3.11 | PaPAM | - |
Pantoea agglomerans |
| 5.4.3.11 | phenylalanine aminomutase | - |
Pantoea agglomerans |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 5.4.3.11 | 31 | - |
assay at | Pantoea agglomerans |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.11 | 0.003 | - |
2-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.013 | - |
4-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.022 | - |
4-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.022 | - |
2-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.023 | - |
4-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.026 | - |
3-thiophen-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.031 | - |
3-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.038 | - |
4-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.045 | - |
4-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.053 | - |
4-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.058 | - |
3-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.064 | - |
2-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.143 | - |
3-thiophen-3-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.146 | - |
3-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.209 | - |
3-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.236 | - |
3-furan-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.301 | - |
L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.42 | - |
3-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.484 | - |
3-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 5.4.3.11 | 8 | - |
assay at | Pantoea agglomerans |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.4.3.11 | 4-methylidene-1H-imidazol-5(4H)-one | MIO, prosthetic group, dependent on, proposed elimination mechanisms for the displacement of the NH2-MIO adduct. Formation of an NH2-MIO adduct, where the amino group of the substrate is covalently attached to the enzyme during alpha/beta-isomerization | Pantoea agglomerans | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 5.4.3.11 | evolution | the enzyme belongs to a class I lyase-like superfamily of catalysts, along with other MIO-dependent aminomutases | Pantoea agglomerans |
| 5.4.3.11 | additional information | enzyme structure-activity analysis and modeling of substrate-PaPAM structural interactions, overview | Pantoea agglomerans |
| 5.4.3.11 | physiological function | PaPAM makes the (3S)-beta-phenylalanine antipode on the biosynthetic pathway to the antibiotic andrimid starting from (S)-beta-phenylalanine via (S)-alpha-phenylalanine | Pantoea agglomerans |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.3.11 | 0.019 | - |
4-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.02 | - |
2-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.05 | - |
4-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.051 | - |
L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.082 | - |
4-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.09 | - |
4-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.11 | - |
4-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.19 | - |
3-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.19 | - |
3-thiophen-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.21 | - |
3-methoxy-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.31 | - |
2-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.34 | - |
3-nitro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.428 | - |
3-thiophen-3-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.588 | - |
3-furan-2-yl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.73 | - |
2-methyl-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 0.79 | - |
4-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 1.12 | - |
3-chloro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 1.2 | - |
3-fluoro-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
| 5.4.3.11 | 1.24 | - |
3-bromo-L-phenylalanine | pH 8.0, 31°C, recombinant enzyme | Pantoea agglomerans | |
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