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Literature summary for 3.1.8.1 extracted from

  • Bigley, A.N.; Xiang, D.F.; Narindoshvili, T.; Burgert, C.W.; Hengge, A.C.; Raushel, F.M.
    Transition State Analysis of the Reaction Catalyzed by the Phosphotriesterase from Sphingobium sp. TCM1 (2019), Biochemistry, 58, 1246-1259 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.1.8.1

KM Value [mM]

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

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

Organism UniProt Comment Textmining
Sphingobium sp. TCM1 A0A077JBW9
-
-

Reaction

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
a

Substrates and Products (Substrate)

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

Synonyms Comment Organism
HAD
-
 Sphingobium sp. TCM1
haloalkylphosphorus hydrolase
-
 Sphingobium sp. TCM1
Sb-PTE
-
 Sphingobium sp. TCM1

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25 30 assay at Sphingobium sp. TCM1

Turnover Number [1/s]

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

pH Optimum Minimum pH Optimum Maximum Comment Organism
9 10 assay at Sphingobium sp. TCM1

kcat/KM [mM/s]

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