Activating Compound | Comment | Organism | Structure |
---|---|---|---|
ascorbate | required | Pseudomonas sp. |
Cloned (Comment) | Organism |
---|---|
recombinant expression of His-tagged enzyme | Pseudomonas sp. |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
(3-carboxy-2-oxopropyl)(trimethyl)arsanium | - |
Pseudomonas sp. | |
(3-carboxy-2-oxopropyl)(trimethyl)phosphanium | - |
Pseudomonas sp. | |
(3-carboxypropyl)(trimethyl)arsanium | - |
Pseudomonas sp. | |
(3-carboxypropyl)(trimethyl)phosphanium | - |
Pseudomonas sp. | |
N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine | - |
Pseudomonas sp. | |
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium | - |
Pseudomonas sp. | |
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium | - |
Pseudomonas sp. | |
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium | - |
Pseudomonas sp. | |
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium | - |
Pseudomonas sp. |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
additional information | - |
additional information | kinetic analysis, overview | Pseudomonas sp. | |
1 | - |
4-Trimethylammoniobutanoate | pH 7.5, 23°C | Pseudomonas sp. | |
1.2 | - |
(3-carboxypropyl)(trimethyl)phosphanium | pH 7.5, 23°C | Pseudomonas sp. | |
1.37 | - |
(3-carboxypropyl)(trimethyl)arsanium | pH 7.5, 23°C | Pseudomonas sp. |
Metals/Ions | Comment | Organism | Structure |
---|---|---|---|
Fe2+ | nonheme Fe2+-dependent oxygenase, dependent on, required for catalysis, bound to the active site | Pseudomonas sp. |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
4-trimethylammoniobutanoate + 2-oxoglutarate + O2 | Pseudomonas sp. | - |
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 | - |
? | |
4-trimethylammoniobutanoate + 2-oxoglutarate + O2 | Pseudomonas sp. AK-1 | - |
3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Pseudomonas sp. | P80193 | - |
- |
Pseudomonas sp. AK-1 | P80193 | - |
- |
Purification (Comment) | Organism |
---|---|
recombinant His-tagged enzyme by nickel affinity chromatography, gel filtration, ultrafiltration, and buffer exchange via desalting gel filtration | Pseudomonas sp. |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(3-carboxypropyl)(trimethyl)arsanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | [(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + succinate + CO2 | - |
? | |
(3-carboxypropyl)(trimethyl)arsanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. AK-1 | [(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + succinate + CO2 | - |
? | |
(3-carboxypropyl)(trimethyl)phosphanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | [(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + succinate + CO2 | - |
? | |
(3-carboxypropyl)(trimethyl)phosphanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. AK-1 | [(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + succinate + CO2 | - |
? | |
4-trimethylammoniobutanoate + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | 3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 | - |
? | |
4-trimethylammoniobutanoate + 2-oxoglutarate + O2 | - |
Pseudomonas sp. AK-1 | 3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 | - |
? | |
additional information | cation-Pi interactions contribute to substrate recognition in gamma-butyrobetaine hydroxylase catalysis. BBOX contains an aromatic cage for the recognition of the positively charged trimethylammonium group of the gamma-butyrobetaine substrate. Substrate analogues (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium with P and As substituting for N in the trimethylammonium group are good BBOX substrates, which follow the efficiency trend N+ >P+ >As+. An uncharged carbon analogue N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine of gamma-butyrobetaine is not a BBOX substrate. Importance of the energetically favorable cation-Pi interactions in productive substrate recognition. Homology modeling of binding modes and structures of (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium to psBBOX using an X-ray crystal structure of human BBOX in complex with ZnII, N-oxalylglycine, and gamma-butyrobetaine, PDB ID 3O2G, quantum mechanical calculations and docking simulations. Substrate specificity, overview | Pseudomonas sp. | ? | - |
? | |
additional information | cation-Pi interactions contribute to substrate recognition in gamma-butyrobetaine hydroxylase catalysis. BBOX contains an aromatic cage for the recognition of the positively charged trimethylammonium group of the gamma-butyrobetaine substrate. Substrate analogues (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium with P and As substituting for N in the trimethylammonium group are good BBOX substrates, which follow the efficiency trend N+ >P+ >As+. An uncharged carbon analogue N-(3-hydroxypyridine-2-carbonyl)-S-[(pyridin-2-yl)methyl]-L-cysteine of gamma-butyrobetaine is not a BBOX substrate. Importance of the energetically favorable cation-Pi interactions in productive substrate recognition. Homology modeling of binding modes and structures of (3-carboxypropyl)(trimethyl)phosphanium and (3-carboxypropyl)(trimethyl)arsanium to psBBOX using an X-ray crystal structure of human BBOX in complex with ZnII, N-oxalylglycine, and gamma-butyrobetaine, PDB ID 3O2G, quantum mechanical calculations and docking simulations. Substrate specificity, overview | Pseudomonas sp. AK-1 | ? | - |
? | |
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | (3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2 | - |
? | |
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. AK-1 | (3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2 | - |
? | |
[(2R)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | (3-carboxy-2-oxopropyl)(trimethyl)phosphanium + succinate + CO2 | - |
? | |
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)arsanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | (3-carboxy-2-oxopropyl)(trimethyl)arsanium + succinate + CO2 | - |
? | |
[(2S)-3-carboxy-2-hydroxypropyl](trimethyl)phosphanium + 2-oxoglutarate + O2 | - |
Pseudomonas sp. | (3-carboxy-2-oxopropyl)(trimethyl)phosphanium + succinate + CO2 | - |
? |
Synonyms | Comment | Organism |
---|---|---|
BBOX | - |
Pseudomonas sp. |
gamma-butyrobetaine hydroxylase | - |
Pseudomonas sp. |
psBBOX | - |
Pseudomonas sp. |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
23 | - |
assay at | Pseudomonas sp. |
Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
2.61 | - |
(3-carboxypropyl)(trimethyl)arsanium | pH 7.5, 23°C | Pseudomonas sp. | |
4.13 | - |
(3-carboxypropyl)(trimethyl)phosphanium | pH 7.5, 23°C | Pseudomonas sp. | |
7.02 | - |
4-Trimethylammoniobutanoate | pH 7.5, 23°C | Pseudomonas sp. |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.5 | - |
assay at | Pseudomonas sp. |
General Information | Comment | Organism |
---|---|---|
evolution | the enzyme belongs to the 2-oxoglutarate/Fe(II) dependent oxygenase family | Pseudomonas sp. |
physiological function | gamma-butyrobetaine hydroxylase (BBOX) is a nonheme Fe(II)- and 2-oxoglutarate-dependent oxygenase that catalyzes the stereoselective hydroxylation of an unactivated C-H bond of gamma-butyrobetaine in the final step of carnitine biosynthesis | Pseudomonas sp. |