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Literature summary for 2.3.1.47 extracted from
- Inhibition of 7,8-diaminopelargonic acid aminotransferase from Mycobacterium tuberculosis by chiral and achiral anologs of its substrate: biological implications (2009), Biochimie, 91, 826-834.
Application
| Application | Comment | Organism |
|---|---|---|
| medicine | enzyme is a potential target for antimycobacterial drugs | Escherichia coli |
| medicine | enzyme is a potential target for antimycobacterial drugs | Mycobacterium tuberculosis |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| histidine-tagged enzyme is expressed in Escherichia coli C268 | Escherichia coli |
| histidine-tagged enzyme is expressed in Escherichia coli C268 | Mycobacterium tuberculosis |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (R)-8-amino-7-oxononanoic acid | no inhibition up to 15 microM with 94.6% ee (S)-enantiomer as substrate, beyond that strong inhibitor of both enzyme forms, binding to active site | Escherichia coli |  |
| (R)-8-amino-7-oxononanoic acid | no inhibition up to 15 microM with 94.6% ee (S)-enantiomer as substrate, beyond that strong inhibitor of both enzyme forms, binding to active site | Mycobacterium tuberculosis | |
| 8-amino-7-oxooctanoic acid | achiral analog of substrate, strong inhibitor of both enzyme forms, binding to active site | Mycobacterium tuberculosis | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0013 | - |
(S)-8-amino-7-oxononanoic acid | calculated from the competitive and uncompetitive constants and the substrate concentration determined in inhibitor experiments, 37°C, pH 8.6 | Mycobacterium tuberculosis | |
| 0.0014 | - |
S-adenosyl-L-methionine | calculated from the competitive and uncompetitive constants and the substrate concentration determined in inhibitor experiments, 37°C, pH 8.6 | Mycobacterium tuberculosis | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | Mycobacterium tuberculosis | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic acid | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | Escherichia coli | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | Escherichia coli C268 | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Escherichia coli | - |
C268 | - |
| Escherichia coli C268 | - |
C268 | - |
| Mycobacterium tuberculosis | - |
- |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 8.6% product is formed matching the portion of S-enantiomer substrate (9.3%),37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, 1 mM S-adenosyl-L-methionine, 10 microM (R)-8-amino-7-oxononanoic acid | Mycobacterium tuberculosis | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + (R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 46.3% product is formed from the racemic substrate, 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, 1 mM S-adenosyl-L-methionine, 2 microM racemic 8-amino-7-oxononanoic acid | Mycobacterium tuberculosis | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic acid | Mycobacterium tuberculosis | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration | Escherichia coli | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 93.2% product is formed matching the portion of S-enantiomer substrate (94.6%), 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic acid | Mycobacterium tuberculosis | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
| (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine | 37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration | Escherichia coli C268 | (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| dimer | 2 * ? | Escherichia coli |
| dimer | 2 * ?, modeling with Escherichia coli enzyme as template | Mycobacterium tuberculosis |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| 7,8-diaminopelargonic acid aminotransferase | - |
Escherichia coli |
| 7,8-diaminopelargonic acid aminotransferase | - |
Mycobacterium tuberculosis |
| bioF protein | - |
Escherichia coli |
| bioF protein | - |
Mycobacterium tuberculosis |
| DAPA AT | - |
Escherichia coli |
| DAPA AT | - |
Mycobacterium tuberculosis |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| pyridoxal 5'-phosphate | - |
Escherichia coli | |
| pyridoxal 5'-phosphate | - |
Mycobacterium tuberculosis | |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | dimethyl-8-amino-7-oxooctanoic acid, an achiral substrate analogue, does not inhibit the enzyme | Mycobacterium tuberculosis | |
| 0.0009 | - |
8-amino-7-oxooctanoic acid | achiral substrate analogue, competitive constant, pyridoxamine 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, 2.5 mM S-adenosyl-L-methionine and varicous concentrations of (S)-8-amino-7-oxononanoic acid, 0-100 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0017 | - |
(R)-8-amino-7-oxononanoic acid | competitive constant, pyridoxamine 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, 2.5 mM S-adenosyl-L-methionine and various concentrations of (S)-8-amino-7-oxononanoic acid, 0.2-19.2 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0033 | - |
(R)-8-amino-7-oxononanoic acid | uncompetitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-20 microM inhibitor | Escherichia coli | |
| 0.0042 | - |
8-amino-7-oxooctanoic acid | achiral substrate analogue, competitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0-60 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0059 | - |
(R)-8-amino-7-oxononanoic acid | competitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-57.3 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0125 | - |
8-amino-7-oxooctanoic acid | achiral substrate analogue, uncompetitive constant, pyridoxamine 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, 2.5 mM S-adenosyl-L-methionine and varicous concentrations of (S)-8-amino-7-oxononanoic acid, 0-100 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0134 | - |
(R)-8-amino-7-oxononanoic acid | uncompetitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-57.3 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0152 | - |
8-amino-7-oxooctanoic acid | achiral substrate analogue, uncompetitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0-60 microM inhibitor | Mycobacterium tuberculosis | |
| 0.0153 | - |
(R)-8-amino-7-oxononanoic acid | competitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-20 microM inhibitor | Escherichia coli | |
| 0.0162 | - |
(R)-8-amino-7-oxononanoic acid | uncompetitive constant, pyridoxamine 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, 2.5 mM S-adenosyl-L-methionine and various concentrations of (S)-8-amino-7-oxononanoic acid, 0.2-19.2 microM inhibitor | Mycobacterium tuberculosis | |
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