Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • Mann, S.; Colliandre, L.; Labesse, G.; Ploux, O.
    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.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.3.1.47 medicine enzyme is a potential target for antimycobacterial drugs Escherichia coli
2.3.1.47 medicine enzyme is a potential target for antimycobacterial drugs Mycobacterium tuberculosis
2.6.1.62 analysis analytical method to measure the enantiomeric excess of substrate 8-amino-7-oxononanoic acid, based on the derivatization of its amine function, by orthophtalaldehyde and N-acetyl-L-cysteine, followed by high pressure liquid chromatography separation. Using this methodology and enantiopure samples of 8-amino-7-oxononanoic acid, it appears that racemization of 8-amino-7-oxononanoic acid occurs rapidly with half-lives from 1 to 8 h, not only in 4 M HCl but also in the usual pH range, from 7 to 9 Mycobacterium tuberculosis

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.47 histidine-tagged enzyme is expressed in Escherichia coli C268 Escherichia coli
2.3.1.47 histidine-tagged enzyme is expressed in Escherichia coli C268 Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.47 (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
2.3.1.47 (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
2.3.1.47 8-amino-7-oxooctanoic acid achiral analog of substrate, strong inhibitor of both enzyme forms, binding to active site Mycobacterium tuberculosis
2.6.1.62 (R)-8-amino-7-oxononanoate binds both to the pyridoxal 5'-phosphate form and to the pyridoxamine 5'-phosphate form by forming specific hydrogen bonds with residue T309 and the phosphate group of the cofactor Mycobacterium tuberculosis
2.6.1.62 (R)-8-amino-7-oxononanoic acid potent inhibitor Mycobacterium tuberculosis
2.6.1.62 8-amino-7-oxooctanoate potent inhibitor Mycobacterium tuberculosis
2.6.1.62 8-amino-7-oxooctanoic acid achiral analog of 8-amino-7-oxononanoate Mycobacterium tuberculosis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.47 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
2.3.1.47 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)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.3.1.47 (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

EC Number Organism UniProt Comment Textmining
2.3.1.47 Escherichia coli
-
 C268
-
2.3.1.47 Escherichia coli C268
-
 C268
-
2.3.1.47 Mycobacterium tuberculosis
-
-
-
2.6.1.62 Mycobacterium tuberculosis
-
-
-
2.6.1.62 Mycobacterium tuberculosis P9WQ81
-
-
2.6.1.62 Mycobacterium tuberculosis ATCC 25618 P9WQ81
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.3.1.47 (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)
-
 ?
2.6.1.62 S-adenosyl-L-methionine + (S)-8-amino-7-oxononanoate enzyme only uses (S)-8-amino-7-oxononanoate as substrate Mycobacterium tuberculosis S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate
-
 ?
2.6.1.62 S-adenosyl-L-methionine + (S)-8-amino-7-oxononanoate enzyme only uses (S)-8-amino-7-oxononanoate as substrate Mycobacterium tuberculosis ATCC 25618 S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate
-
 ?
2.6.1.62 S-adenosyl-L-methionine + (S)-8-amino-7-oxononanoic acid
-
 Mycobacterium tuberculosis S-adenosyl-4-methylthio-2-oxobutanoate + (7S,8R)-diaminononanoate
-
 ?

Subunits

EC Number Subunits Comment Organism
2.3.1.47 dimer 2 * ? Escherichia coli
2.3.1.47 dimer 2 * ?, modeling with Escherichia coli enzyme as template Mycobacterium tuberculosis

Synonyms

EC Number Synonyms Comment Organism
2.3.1.47 7,8-diaminopelargonic acid aminotransferase
-
 Escherichia coli
2.3.1.47 7,8-diaminopelargonic acid aminotransferase
-
 Mycobacterium tuberculosis
2.3.1.47 bioF protein
-
 Escherichia coli
2.3.1.47 bioF protein
-
 Mycobacterium tuberculosis
2.3.1.47 DAPA AT
-
 Escherichia coli
2.3.1.47 DAPA AT
-
 Mycobacterium tuberculosis
2.6.1.62 7,8-diaminopelargonic acid aminotransferase
-
 Mycobacterium tuberculosis
2.6.1.62 DAPA AT
-
 Mycobacterium tuberculosis
2.6.1.62 S-adenosyl-L-methionine:8-amino-7-oxononanoate aminotransferase
-
 Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
2.3.1.47 pyridoxal 5'-phosphate
-
 Escherichia coli
2.3.1.47 pyridoxal 5'-phosphate
-
 Mycobacterium tuberculosis
2.6.1.62 pyridoxal 5'-phosphate
-
 Mycobacterium tuberculosis
2.6.1.62 pyridoxamine 5'-phosphate
-
 Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.3.1.47 additional information
-
 additional information dimethyl-8-amino-7-oxooctanoic acid, an achiral substrate analogue, does not inhibit the enzyme Mycobacterium tuberculosis
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.3.1.47 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
2.6.1.62 0.0009
-
 8-amino-7-oxooctanoate bound to the pyridoxamine 5'-phosphate form, 100 mM EPPS buffer, pH 8.6 Mycobacterium tuberculosis
2.6.1.62 0.0009
-
 8-amino-7-oxooctanoic acid binding to the the pyridoxamine 5'-phosphate form of enzyme, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
2.6.1.62 0.0017
-
 (R)-8-amino-7-oxononanoic acid bound to the pyridoxamine 5'-phosphate form, 100 mM EPPS buffer, pH 8.6 Mycobacterium tuberculosis
2.6.1.62 0.0017
-
 (R)-8-amino-7-oxononanoate binding to the the pyridoxamine 5'-phosphate form of enzyme, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
2.6.1.62 0.0042
-
 8-amino-7-oxooctanoate bound to the pyridoxal 5'-phosphate form, 100 mM EPPS buffer, pH 8.6 Mycobacterium tuberculosis
2.6.1.62 0.0042
-
 8-amino-7-oxooctanoic acid binding to the the pyridoxal 5'-phosphate form of enzyme, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
2.6.1.62 0.0059
-
 (R)-8-amino-7-oxononanoic acid bound to the pyridoxal 5'-phosphate enzyme form, 100 mM EPPS buffer, pH 8.6 Mycobacterium tuberculosis
2.6.1.62 0.0059
-
 (R)-8-amino-7-oxononanoate binding to the the pyridoxal 5'-phosphate form of enzyme, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis