KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
additional information | - |
additional information | heavy atom isotope effect measurements, competitive method | Sphingobium sp. TCM1 | |
0.05 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.085 | - |
O,O,S-tributyl phosphorothioate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.088 | - |
(1E)-but-1-en-1-yl dibutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.11 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.14 | - |
dibutyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.15 | - |
dibutyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.17 | - |
dibutyl 3,3-difluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.24 | - |
diethyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.25 | - |
diethyl 3-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.27 | - |
diethyl 3-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.32 | - |
diethyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.39 | - |
diethyl 2,4-difluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.41 | - |
diethyl 4-chlorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.43 | - |
dibutyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.44 | - |
diethyl 4-methoxyphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.46 | - |
diethyl pentafluoro-phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.55 | - |
4-carbamoylphenyl diethyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.63 | - |
diethyl 2-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.67 | - |
diethyl 4-cyanophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.95 | - |
diethyl 2,4,6-trifluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1 | - |
methyl 4-[(diethoxyphosphoryl)oxy]benzoate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1.1 | - |
diethyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1.1 | - |
diethyl 2,6-difluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1.2 | - |
diethyl 4-formylphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1.3 | - |
diethyl 2-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
1.6 | - |
diethyl 4-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 |
Metals/Ions | Comment | Organism | Structure |
---|---|---|---|
additional information | structure of the binuclear metal center in Sb-PTE with coordinating nitrogens from the four histidine ligands, overview | Sphingobium sp. TCM1 |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Sphingobium sp. TCM1 | A0A077JBW9 | - |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
an aryl dialkyl phosphate + H2O = dialkyl phosphate + an aryl alcohol | reaction mechanism analysis, overview. The phosphoryl oxygen and one of the ester oxygens bind in a bidentate manner to the beta-metal allowing polarization of the phosphorus center. The bridging hydroxide attacks the phosphorus center forming a phosphorane-like transition state with delocalization of charge supported by coordination to the metal as well as the electronegative ester groups. Once the phosphorane species is formed, the pKa of the attacking OH group will be drastically reduced and the proton can be passed to Glu407. In the substrate-docked structure of Sb-PTE, the free oxygen of Glu407 is 4.0 A from the leaving group oxygen, which would enable transfer of the proton to the leaving group, facilitating the collapse of the phosphorane intermediate into products | Sphingobium sp. TCM1 |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(1E)-but-1-en-1-yl dibutyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
4-carbamoylphenyl diethyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate + H2O | low activity | Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
dibutyl 3,3-difluorobutyl phosphate + H2O | very low activity | Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
dibutyl 3,3-difluorobutyl phosphate + H2O | low activity | Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
dibutyl 4-acetophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + 4-hydroxyacetophenone | - |
? | |
dibutyl 4-nitrophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + 4-nitrophenol | - |
? | |
dibutyl phenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + phenol | - |
? | |
diethyl 2,4,6-trifluorophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 2,4,6-trifluorophenol | - |
? | |
diethyl 2,4-difluorophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 2,4-difluorophenol | - |
? | |
diethyl 2,6-difluoro-4-nitrophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 2,6-difluoro-4-nitrophenol | - |
? | |
diethyl 2-fluoro-4-nitrophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 2-fluoro-4-nitrophenol | - |
? | |
diethyl 2-fluorophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 2-fluorophenol | - |
? | |
diethyl 3-fluoro-4-nitrophenyl phosphate + H2O | best substrate | Sphingobium sp. TCM1 | diethyl phosphate + 3-fluoro-4-nitrophenol | - |
? | |
diethyl 3-fluorophenyl phosphate + H2O | high activity | Sphingobium sp. TCM1 | diethyl phosphate + 4-fluorophenol | - |
? | |
diethyl 4-acetophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-hydroxyacetophenone | - |
? | |
diethyl 4-chlorophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-chlorophenol | - |
? | |
diethyl 4-cyanophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-hydroxybenzonitril | - |
? | |
diethyl 4-fluorophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-fluorophenol | - |
? | |
diethyl 4-formylphenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-formylphenol | - |
? | |
diethyl 4-methoxyphenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-methoxyphenol | - |
? | |
diethyl 4-nitrophenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-nitrophenol | - |
? | |
diethyl pentafluoro-phenyl phosphate + H2O | high activity | Sphingobium sp. TCM1 | diethyl phosphate + 2,3,4,5,6-pentafluorophenol | - |
? | |
diethyl phenyl phosphate + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + phenol | - |
? | |
methyl 4-[(diethoxyphosphoryl)oxy]benzoate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
additional information | enzyme substrate specificity analysis, optimization of the assay method, overview. Sb-PTE is capable of hydrolyzing a wide range of organophosphate triester substrates. Broensted analysis, P-O bond cleavage is rate limiting for kcat and kcat/Km for the dibutyl series of substrates tested. The enzyme must be able to effectively protonate the leaving group for efficient catalysis, but the lack of loss of activity at high pH is inconsistent with a separate general acid serving this role, unless it occurs after the rate-limiting step. The absence of a solvent viscosity effect and the magnitude of the 18O-isotope effects are consistent with nucleophilic attack of hydroxide as the rate-limiting step during the hydrolysis of substrates by this enzyme | Sphingobium sp. TCM1 | ? | - |
? | |
O,O,S-tributyl phosphorothioate + H2O | - |
Sphingobium sp. TCM1 | dibutyl phosphate + ? | - |
? | |
paraoxon + H2O | - |
Sphingobium sp. TCM1 | diethyl phosphate + 4-nitrophenol | - |
? |
Synonyms | Comment | Organism |
---|---|---|
HAD | - |
Sphingobium sp. TCM1 |
haloalkylphosphorus hydrolase | - |
Sphingobium sp. TCM1 |
Sb-PTE | - |
Sphingobium sp. TCM1 |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
25 | 30 | assay at | Sphingobium sp. TCM1 |
Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.043 | - |
dibutyl 3,3-difluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.045 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.36 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.42 | - |
O,O,S-tributyl phosphorothioate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.6 | - |
diethyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.8 | - |
4-carbamoylphenyl diethyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
0.83 | - |
(1E)-but-1-en-1-yl dibutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
2.5 | - |
diethyl 4-methoxyphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
2.5 | - |
dibutyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
3.2 | - |
methyl 4-[(diethoxyphosphoryl)oxy]benzoate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
4.4 | - |
dibutyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
7.5 | - |
dibutyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
13 | - |
diethyl 2,4-difluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
21 | - |
diethyl 2-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
31 | - |
diethyl 4-formylphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
32 | - |
diethyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
40 | - |
diethyl 4-chlorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
40 | - |
diethyl 2-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
71 | - |
diethyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
71 | - |
diethyl 2,4,6-trifluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
78 | - |
diethyl 4-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
81 | - |
diethyl 3-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
93 | - |
diethyl 2,6-difluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
93 | - |
diethyl 4-cyanophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
107 | - |
diethyl 3-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
167 | - |
diethyl pentafluoro-phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
9 | 10 | assay at | Sphingobium sp. TCM1 |
kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.25 | - |
dibutyl 3,3-difluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
0.9 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
1.45 | - |
4-carbamoylphenyl diethyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
2.5 | - |
diethyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
3.2 | - |
methyl 4-[(diethoxyphosphoryl)oxy]benzoate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
3.27 | - |
dibutyl 2,2,3,3-tetrafluorobutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
4.94 | - |
O,O,S-tributyl phosphorothioate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
5.68 | - |
diethyl 4-methoxyphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
5.81 | - |
dibutyl 4-acetophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
9.43 | - |
(1E)-but-1-en-1-yl dibutyl phosphate | pH 9.0, 25°C | Sphingobium sp. TCM1 | |
16.15 | - |
diethyl 2-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
25.8 | - |
diethyl 4-formylphenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
31.4 | - |
dibutyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
33.3 | - |
diethyl 2,4-difluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
48.75 | - |
diethyl 4-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
50 | - |
dibutyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
63.5 | - |
diethyl 2-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
64.54 | - |
diethyl phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
74.7 | - |
diethyl 2,4,6-trifluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
84.54 | - |
diethyl 2,6-difluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
97.6 | - |
diethyl 4-chlorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
100 | - |
diethyl 4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
138.8 | - |
diethyl 4-cyanophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
300 | - |
diethyl 3-fluorophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
363.04 | - |
diethyl pentafluoro-phenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 | |
428 | - |
diethyl 3-fluoro-4-nitrophenyl phosphate | pH and temperature not specified in the publication | Sphingobium sp. TCM1 |