BRENDA - Enzyme Database

The 2-oxoglutarate binding site of prolyl 4-hydroxylase. Identification of distinct subsites and evidence for 2-oxoglutarate decarboxylation in a ligand reaction at the enzyme-bound ferrous ion

Majamaa, K.; Hanauske-Abel, H.M.; Gunzler, V.; Kivirikko, K.I.; Eur. J. Biochem. 138, 239-245 (1984)

Data extracted from this reference:

Activating Compound
EC Number
Activating Compound
Commentary
Organism
Structure
1.14.11.2
bovine serum albumin
activation
Gallus gallus
1.14.11.2
catalase
activation
Gallus gallus
1.14.11.2
dithiothreitol
activation
Gallus gallus
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
1.14.11.2
2-oxoadipinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
2-oxobutyrate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
2-oxosuccinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+; i.e. oxaloacetate
Gallus gallus
1.14.11.2
2-oxovalerate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
3-oxoglutarate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
adipinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
benzene 1,2-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzene 1,3-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzene 1,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzoate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Glutarate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
levulinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
malonate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 2,3-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 2,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 2,5-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 2,6-dicarboxylate
competitive with respect to Fe2+ and noncompetitive with respect to 2-oxoglutarate
Gallus gallus
1.14.11.2
pyridine 2-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 3,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 3,5-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 3-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 4-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyruvate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
succinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
KM Value [mM]
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.14.11.2
0.14
-
2-oxoadipinate
as cosubstrate
Gallus gallus
Metals/Ions
EC Number
Metals/Ions
Commentary
Organism
Structure
1.14.11.2
Fe2+
-
Gallus gallus
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
1.14.11.2
Gallus gallus
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
1.14.11.2
embryo
-
Gallus gallus
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.14.11.2
(Pro-Pro-Gly)n + 2-oxoglutarate + O2
n: 1,5,10
439193
Gallus gallus
(Pro-4-hydroxy-Pro-Gly)n + succinate + CO2
n: 1,5,10
439193
Gallus gallus
?
1.14.11.2
additional information
thermal denaturing of the triple-helical conformation of the substrate before hydroxylation
439193
Gallus gallus
?
-
-
-
-
1.14.11.2
additional information
characterization of the 2-oxoglutarate binding site of the enzyme, 2-oxosuccinate, 2-oxovalerate, 2-oxobutyrate, 3-oxoglutarate or pyridine 2,5-dicarboxylate do not replace 2-oxoglutarate as cosubstrates
439193
Gallus gallus
?
-
-
-
-
1.14.11.2
protocollagen + 2-oxoglutarate + O2
2-oxoadipate can replace 2-oxoglutarate as cosubstrate
439193
Gallus gallus
4-hydroxyproline containing protocollagen + succinate + CO2
-
439193
Gallus gallus
?
Temperature Optimum [°C]
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.14.11.2
37
-
assay at
Gallus gallus
pH Optimum
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.14.11.2
7.8
-
assay at
Gallus gallus
Cofactor
EC Number
Cofactor
Commentary
Organism
Structure
1.14.11.2
ascorbate
-
Gallus gallus
Ki Value [mM]
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
1.14.11.2
0.0008
-
Pyridine-2,5-dicarboxylate
-
Gallus gallus
1.14.11.2
0.002
-
Pyridine-2,4-dicarboxylate
-
Gallus gallus
1.14.11.2
0.025
-
pyridine 2-carboxylate
-
Gallus gallus
1.14.11.2
0.1
-
2-oxosuccinate
-
Gallus gallus
1.14.11.2
0.21
-
pyridine 2,3-dicarboxylate
-
Gallus gallus
1.14.11.2
0.4
-
succinate
-
Gallus gallus
1.14.11.2
0.5
-
pyridine 3-carboxylate
-
Gallus gallus
1.14.11.2
0.8
-
3-oxoglutarate
-
Gallus gallus
1.14.11.2
0.9
-
2-oxoadipinate
-
Gallus gallus
1.14.11.2
0.9
-
Pyridine 3,5-dicarboxylate
-
Gallus gallus
1.14.11.2
0.9
-
Pyridine 4-carboxylate
-
Gallus gallus
1.14.11.2
2.2
-
Pyridine 3,4-dicarboxylate
-
Gallus gallus
1.14.11.2
3.3
-
Benzene 1,4-dicarboxylate
-
Gallus gallus
1.14.11.2
4.2
-
Glutarate
-
Gallus gallus
1.14.11.2
5.8
-
Benzene 1,3-dicarboxylate
-
Gallus gallus
1.14.11.2
5.9
-
malonate
-
Gallus gallus
1.14.11.2
7.6
-
2-oxobutyrate
-
Gallus gallus
1.14.11.2
9.4
-
2-oxovalerate
-
Gallus gallus
1.14.11.2
9.9
-
Benzoate
-
Gallus gallus
1.14.11.2
10
-
benzene 1,2-dicarboxylate
value above
Gallus gallus
1.14.11.2
15
-
adipinate
value above
Gallus gallus
1.14.11.2
15
-
levulinate
value above
Gallus gallus
1.14.11.2
15
-
pyruvate
-
Gallus gallus
Activating Compound (protein specific)
EC Number
Activating Compound
Commentary
Organism
Structure
1.14.11.2
bovine serum albumin
activation
Gallus gallus
1.14.11.2
catalase
activation
Gallus gallus
1.14.11.2
dithiothreitol
activation
Gallus gallus
Cofactor (protein specific)
EC Number
Cofactor
Commentary
Organism
Structure
1.14.11.2
ascorbate
-
Gallus gallus
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
1.14.11.2
2-oxoadipinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
2-oxobutyrate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
2-oxosuccinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+; i.e. oxaloacetate
Gallus gallus
1.14.11.2
2-oxovalerate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
3-oxoglutarate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
adipinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
benzene 1,2-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzene 1,3-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzene 1,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Benzoate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Glutarate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
levulinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
malonate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 2,3-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 2,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 2,5-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 2,6-dicarboxylate
competitive with respect to Fe2+ and noncompetitive with respect to 2-oxoglutarate
Gallus gallus
1.14.11.2
pyridine 2-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 3,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 3,5-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyridine 3-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
Pyridine 4-carboxylate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
pyruvate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
1.14.11.2
succinate
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
Gallus gallus
Ki Value [mM] (protein specific)
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
1.14.11.2
0.0008
-
Pyridine-2,5-dicarboxylate
-
Gallus gallus
1.14.11.2
0.002
-
Pyridine-2,4-dicarboxylate
-
Gallus gallus
1.14.11.2
0.025
-
pyridine 2-carboxylate
-
Gallus gallus
1.14.11.2
0.1
-
2-oxosuccinate
-
Gallus gallus
1.14.11.2
0.21
-
pyridine 2,3-dicarboxylate
-
Gallus gallus
1.14.11.2
0.4
-
succinate
-
Gallus gallus
1.14.11.2
0.5
-
pyridine 3-carboxylate
-
Gallus gallus
1.14.11.2
0.8
-
3-oxoglutarate
-
Gallus gallus
1.14.11.2
0.9
-
2-oxoadipinate
-
Gallus gallus
1.14.11.2
0.9
-
Pyridine 3,5-dicarboxylate
-
Gallus gallus
1.14.11.2
0.9
-
Pyridine 4-carboxylate
-
Gallus gallus
1.14.11.2
2.2
-
Pyridine 3,4-dicarboxylate
-
Gallus gallus
1.14.11.2
3.3
-
Benzene 1,4-dicarboxylate
-
Gallus gallus
1.14.11.2
4.2
-
Glutarate
-
Gallus gallus
1.14.11.2
5.8
-
Benzene 1,3-dicarboxylate
-
Gallus gallus
1.14.11.2
5.9
-
malonate
-
Gallus gallus
1.14.11.2
7.6
-
2-oxobutyrate
-
Gallus gallus
1.14.11.2
9.4
-
2-oxovalerate
-
Gallus gallus
1.14.11.2
9.9
-
Benzoate
-
Gallus gallus
1.14.11.2
10
-
benzene 1,2-dicarboxylate
value above
Gallus gallus
1.14.11.2
15
-
adipinate
value above
Gallus gallus
1.14.11.2
15
-
levulinate
value above
Gallus gallus
1.14.11.2
15
-
pyruvate
-
Gallus gallus
KM Value [mM] (protein specific)
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.14.11.2
0.14
-
2-oxoadipinate
as cosubstrate
Gallus gallus
Metals/Ions (protein specific)
EC Number
Metals/Ions
Commentary
Organism
Structure
1.14.11.2
Fe2+
-
Gallus gallus
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
1.14.11.2
embryo
-
Gallus gallus
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.14.11.2
(Pro-Pro-Gly)n + 2-oxoglutarate + O2
n: 1,5,10
439193
Gallus gallus
(Pro-4-hydroxy-Pro-Gly)n + succinate + CO2
n: 1,5,10
439193
Gallus gallus
?
1.14.11.2
additional information
thermal denaturing of the triple-helical conformation of the substrate before hydroxylation
439193
Gallus gallus
?
-
-
-
-
1.14.11.2
additional information
characterization of the 2-oxoglutarate binding site of the enzyme, 2-oxosuccinate, 2-oxovalerate, 2-oxobutyrate, 3-oxoglutarate or pyridine 2,5-dicarboxylate do not replace 2-oxoglutarate as cosubstrates
439193
Gallus gallus
?
-
-
-
-
1.14.11.2
protocollagen + 2-oxoglutarate + O2
2-oxoadipate can replace 2-oxoglutarate as cosubstrate
439193
Gallus gallus
4-hydroxyproline containing protocollagen + succinate + CO2
-
439193
Gallus gallus
?
Temperature Optimum [°C] (protein specific)
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.14.11.2
37
-
assay at
Gallus gallus
pH Optimum (protein specific)
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.14.11.2
7.8
-
assay at
Gallus gallus