Protein Variants | Comment | Organism |
---|---|---|
E55D | about 30% decrease in catalytic efficiency | Escherichia coli |
I148L | strong decrease in catalytic efficiency | Escherichia coli |
K292Q | 150% increase in catalytic efficiency | Escherichia coli |
R107K | no decrease in catalytic efficiency | Escherichia coli |
R293K | slight increase in catalytic efficiency | Escherichia coli |
R395K | 4fold increase in Km value, 50% decrease in kcat value | Mycobacterium tuberculosis |
R395K | 90% decrease in catalytic efficiency | Escherichia coli |
R413K | strong decrease in catalytic efficiency | Escherichia coli |
S32A | slight decrease in catalytic efficiency | Escherichia coli |
S391A | minor effect on activity | Mycobacterium tuberculosis |
S391A | slight decrease in catalytic efficiency | Escherichia coli |
S391Y | trace activity | Mycobacterium tuberculosis |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
4-[ethoxy(hydroxy)phosphoryl]-4-oxobutanoic acid | inhibitor shows no significant inhibition of Mycobacterium tuberculosis growth in vitro under aerobic and hypoxic conditions | Mycobacterium tuberculosis | |
4-[hydroxy(methoxy)phosphoryl]-4-oxobutanoic acid | competitive with respect to 2-oxoglutarate, uncompetitive with respect to (+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid. Compound is proposed to bind to the active site and react with thiamine diphosphate but not proceed forward to products by cleavage of the C-P bond | Escherichia coli | |
4-[hydroxy(methoxy)phosphoryl]-4-oxobutanoic acid | inhibitor shows no significant inhibition of Mycobacterium tuberculosis growth in vitro under aerobic and hypoxic conditions | Mycobacterium tuberculosis | |
methyl succinylphosphonate | dead-end inhibitor | Escherichia coli |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.0026 | - |
2-oxoglutarate | mutant K292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0042 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0053 | - |
2-oxoglutarate | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0053 | - |
isochorismate | mutant R395K, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.0091 | - |
2-oxoglutarate | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0099 | - |
2-oxoglutarate | wild-type, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.0099 | - |
2-oxoglutarate | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0099 | - |
2-oxoglutarate | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.01 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R413K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.012 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.012 | - |
2-oxoglutarate | mutant E55D, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.013 | - |
2-oxoglutarate | mutant S391A, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.013 | - |
2-oxoglutarate | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.027 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.036 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.042 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.045 | - |
2-oxoglutarate | mutant R395K, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.045 | - |
2-oxoglutarate | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.05 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.091 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.109 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.2 | - |
2-oxoglutarate | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.22 | - |
2-oxoglutarate | mutant R413K, pH 7.4, temperature not specified in the publication | Escherichia coli |
Metals/Ions | Comment | Organism | Structure |
---|---|---|---|
Mg2+ | Km value 0.044 mM | Escherichia coli | |
Mg2+ | Km value of wild-type 0.044 mM, mutant S391A 0.013 mM | Mycobacterium tuberculosis |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Escherichia coli | - |
- |
- |
Mycobacterium tuberculosis | - |
- |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
isochorismate + 2-oxoglutarate = 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO2 | reaction follows a ping-pong bi-bi mechanism | Escherichia coli |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid + 2-oxoglutarate | analogue of isochorismate, weaker binding to enzyme. Only the (+)-enantiomer is a substrate | Escherichia coli | ? + CO2 | - |
? | |
isochorismate + 2-oxoglutarate | - |
Mycobacterium tuberculosis | (1R,2S,5S,6S)-5-[(1-carboxyethenyl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid + CO2 | - |
? |
Synonyms | Comment | Organism |
---|---|---|
MenD | - |
Escherichia coli |
SEPHCHC synthase | - |
Escherichia coli |
Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.1 | - |
2-oxoglutarate | mutant R413K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.12 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.13 | - |
2-oxoglutarate | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.145 | - |
2-oxoglutarate | mutant R395K, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.17 | - |
2-oxoglutarate | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.18 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.2 | - |
2-oxoglutarate | mutant K292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.22 | - |
2-oxoglutarate | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.22 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.23 | - |
2-oxoglutarate | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.25 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.28 | - |
2-oxoglutarate | wild-type, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.28 | - |
2-oxoglutarate | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.28 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant K292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.3 | - |
2-oxoglutarate | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.3 | - |
2-oxoglutarate | mutant S391A, pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.3 | - |
2-oxoglutarate | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.38 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.4 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.4 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
thiamine diphosphate | Km value 0.008 mM | Escherichia coli | |
thiamine diphosphate | Km value of wild-type 0.008 mM, mutant S391A 0.017 mM, mutant R395K 0.0022 mM, respectively | Mycobacterium tuberculosis |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
0.00013 | - |
4-[hydroxy(methoxy)phosphoryl]-4-oxobutanoic acid | pH 7.4, temperature not specified in the publication | Escherichia coli | |
0.0007 | - |
4-[hydroxy(methoxy)phosphoryl]-4-oxobutanoic acid | pH 7.4, 25°C | Mycobacterium tuberculosis | |
0.016 | - |
4-[ethoxy(hydroxy)phosphoryl]-4-oxobutanoic acid | pH 7.4, 25°C | Mycobacterium tuberculosis |
General Information | Comment | Organism |
---|---|---|
physiological function | enzyme is essential for menaquinone biosynthesis | Escherichia coli |
kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.28 | - |
2-oxoglutarate | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
1 | - |
2-oxoglutarate | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli | |
1 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
2 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
3 | - |
2-oxoglutarate | mutant R395K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
6 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant K292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
6 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
6 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
18 | - |
2-oxoglutarate | mutant E55D, pH 7.4, temperature not specified in the publication | Escherichia coli | |
23 | - |
2-oxoglutarate | mutant S32A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
23 | - |
2-oxoglutarate | mutant S391A, pH 7.4, temperature not specified in the publication | Escherichia coli | |
28 | - |
2-oxoglutarate | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
32 | - |
2-oxoglutarate | mutant R107K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
33 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | wild-type, pH 7.4, temperature not specified in the publication | Escherichia coli | |
33 | - |
2-oxoglutarate | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
77 | - |
2-oxoglutarate | mutant K292Q, pH 7.4, temperature not specified in the publication | Escherichia coli | |
95 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant R293K, pH 7.4, temperature not specified in the publication | Escherichia coli | |
1417 | - |
(+)-5-(carboxymethoxy)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid | mutant I418L, pH 7.4, temperature not specified in the publication | Escherichia coli |