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Literature summary extracted from

  • Sikora, A.L.; Frankel, B.A.; Blanchard, J.S.
    Kinetic and chemical mechanism of arylamine N-acetyltransferase from Mycobacterium tuberculosis (2008), Biochemistry, 47, 10781-10789.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
2.3.1.5 medicine TBNAT remains a potential drug target for the treatment of tuberculosis Mycobacterium tuberculosis

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.5 expressed in Escherichia coli as a His-tagged fusion protein Mycobacterium tuberculosis
2.3.1.5 into the pET28a+ vector for expression in Escherichia coli BL21DE3 cells Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.5 iodoacetamide incubation of TBNAT with iodoacetamide results in a time-dependentloss of enzymatic activity Mycobacterium tuberculosis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.5 0.32
-
 3-Amino-4-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.3.1.5 0.61
-
 hydralazine
-
 Mycobacterium tuberculosis
2.3.1.5 0.9
-
 4-amino-3-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.3.1.5 1.9
-
 2-amino-4-chlorophenol
-
 Mycobacterium tuberculosis
2.3.1.5 2 3 aniline
-
 Mycobacterium tuberculosis
2.3.1.5 3.06
-
 2-amino-4-methylphenol
-
 Mycobacterium tuberculosis
2.3.1.5 5
-
 p-Aminobenzoic acid
-
 Mycobacterium tuberculosis
2.3.1.5 5.79
-
 2-Aminophenol
-
 Mycobacterium tuberculosis
2.3.1.5 6
-
 4-chloroaniline
-
 Mycobacterium tuberculosis
2.3.1.5 11
-
 4-methylaniline
-
 Mycobacterium tuberculosis
2.3.1.5 14
-
 anisidine
-
 Mycobacterium tuberculosis
2.3.1.5 14
-
 nicotinic acid hydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 14
-
 benzoic acid hydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 20
-
 4-hydroxybenzhydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 51
-
 4-fluoroaniline
-
 Mycobacterium tuberculosis
2.3.1.5 102
-
 isoniazid
-
 Mycobacterium tuberculosis

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
2.3.1.5 cytosol
-
 Mycobacterium tuberculosis 5829
-

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.5 30000
-
 SDS-PAGE Mycobacterium tuberculosis
2.3.1.5 30000
-
 determined by SDS-PAGE Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.5 Mycobacterium tuberculosis
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.5 using a Ni-NTA and a Superdex S-75 column Mycobacterium tuberculosis
2.3.1.5 using Ni-NTA chromatography. Approximately 2.7 mg of purified enzyme is obtained per liter of culture Mycobacterium tuberculosis

Reaction

EC Number Reaction Comment Organism Reaction ID
2.3.1.5 acetyl-CoA + an arylamine = CoA + an N-acetylarylamine steady-state kinetic analysis of TBNAT reveals that the enzyme catalyzes the reaction via a bi-bi ping-pong kinetic mechanism: enzyme initially reacts with AcCoA to generate the first product, CoA, and the acetyl-enzyme intermediate (E-Ac). The amine binds and reacts with E-Ac to generate the second product, acetylated amine, and regenerate the free enzyme. The pH dependence of the kinetic parameters reveals that one enzyme group must be deprotonated for optimal catalytic activity and that two amino acid residues at the active site of the free enzyme are involved in binding and/or catalysis. Solvent kinetic isotope effects suggest that proton transfer steps are not rate-limiting in the overall reaction for substituted aniline substrates but become rate-limiting when poor hydrazide substrates are used Mycobacterium tuberculosis
a

Storage Stability

EC Number Storage Stability Organism
2.3.1.5 -20°C, 50% glycerol Mycobacterium tuberculosis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.5 acetyl-CoA + 2-amino-4-chlorophenol
-
 Mycobacterium tuberculosis CoA + N-(5-chloro-2-hydroxyphenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + 2-amino-4-chlorophenol
-
 Mycobacterium tuberculosis CoA + N-acetyl-2-amino-4-chlorophenol
-
 ?
2.3.1.5 acetyl-CoA + 2-amino-4-methylphenol
-
 Mycobacterium tuberculosis CoA + N-(2-hydroxy-5-methylphenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + 2-amino-4-methylphenol
-
 Mycobacterium tuberculosis CoA + N-acetyl-2-amino-4-methylphenol
-
 ?
2.3.1.5 acetyl-CoA + 2-aminophenol
-
 Mycobacterium tuberculosis CoA + N-(2-hydroxyphenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + 2-aminophenol
-
 Mycobacterium tuberculosis CoA + N-acetyl-2-aminophenol
-
 ?
2.3.1.5 acetyl-CoA + 3-amino-4-hydroxybenzoic acid
-
 Mycobacterium tuberculosis CoA + 3-(acetylamino)-4-hydroxybenzoic acid
-
 ?
2.3.1.5 acetyl-CoA + 3-amino-4-hydroxybenzoic acid
-
 Mycobacterium tuberculosis CoA + N-acetyl-3-amino-4-hydroxybenzoic acid
-
 ?
2.3.1.5 acetyl-CoA + 4-amino-3-hydroxybenzoic acid
-
 Mycobacterium tuberculosis CoA + 4-(acetylamino)-3-hydroxybenzoic acid
-
 ?
2.3.1.5 acetyl-CoA + 4-amino-3-hydroxybenzoic acid
-
 Mycobacterium tuberculosis CoA + N-acetyl-4-amino-3-hydroxybenzoic acid
-
 ?
2.3.1.5 acetyl-CoA + 4-chloroaniline
-
 Mycobacterium tuberculosis CoA + N-acetyl-4-chloroaniline
-
 ?
2.3.1.5 acetyl-CoA + 4-chloroaniline
-
 Mycobacterium tuberculosis CoA + N-(4-chlorophenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + 4-fluoroaniline
-
 Mycobacterium tuberculosis CoA + N-(4-fluorophenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + 4-fluoroaniline
-
 Mycobacterium tuberculosis CoA + N-acetyl-4-fluoroaniline
-
 ?
2.3.1.5 acetyl-CoA + 4-hydroxybenzhydrazide
-
 Mycobacterium tuberculosis CoA + N'-acetyl-4-hydroxybenzohydrazide
-
 ?
2.3.1.5 acetyl-CoA + 4-hydroxybenzhydrazide
-
 Mycobacterium tuberculosis CoA + N-acetyl-4-hydroxybenzhydrazide
-
 ?
2.3.1.5 acetyl-CoA + 4-methylaniline
-
 Mycobacterium tuberculosis CoA + N-acetyl-4-methylaniline
-
 ?
2.3.1.5 acetyl-CoA + 4-methylaniline
-
 Mycobacterium tuberculosis CoA + N-(4-methylphenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + aniline
-
 Mycobacterium tuberculosis CoA + N-acetyl-aniline
-
 ?
2.3.1.5 acetyl-CoA + aniline
-
 Mycobacterium tuberculosis CoA + N-phenylacetamide
-
 ?
2.3.1.5 acetyl-CoA + anisidine
-
 Mycobacterium tuberculosis CoA + N-acetyl-anisidine
-
 ?
2.3.1.5 acetyl-CoA + anisidine
-
 Mycobacterium tuberculosis CoA + N-(4-methoxyphenyl)acetamide
-
 ?
2.3.1.5 acetyl-CoA + benzoic acid hydrazide
-
 Mycobacterium tuberculosis CoA + N'-acetylbenzohydrazide
-
 ?
2.3.1.5 acetyl-CoA + benzoic acid hydrazide
-
 Mycobacterium tuberculosis CoA + N-acetyl-benzoic acid hydrazide
-
 ?
2.3.1.5 acetyl-CoA + hydralazine
-
 Mycobacterium tuberculosis CoA + N'-phthalazin-1-ylacetohydrazide
-
 ?
2.3.1.5 acetyl-CoA + hydralazine
-
 Mycobacterium tuberculosis CoA + N-acetyl-hydralazine
-
 ?
2.3.1.5 acetyl-CoA + isoniazid
-
 Mycobacterium tuberculosis CoA + N-acetyl-isoniazid
-
 ?
2.3.1.5 acetyl-CoA + isoniazid
-
 Mycobacterium tuberculosis CoA + N'-acetylpyridine-4-carbohydrazide
-
 ?
2.3.1.5 acetyl-CoA + nicotinic acid hydrazide
-
 Mycobacterium tuberculosis CoA + N'-acetylpyridine-3-carbohydrazide
-
 ?
2.3.1.5 acetyl-CoA + nicotinic acid hydrazide
-
 Mycobacterium tuberculosis CoA + N-acetyl-nicotinic acid hydrazide
-
 ?
2.3.1.5 acetyl-CoA + p-aminobenzoic acid
-
 Mycobacterium tuberculosis CoA + N-acetyl-p-aminobenzoic acid
-
 ?
2.3.1.5 acetyl-CoA + p-aminobenzoic acid
-
 Mycobacterium tuberculosis CoA + 4-(acetylamino)benzoic acid
-
 ?
2.3.1.5 acetyl-CoA + sulfamethoxazole
-
 Mycobacterium tuberculosis CoA + N-[4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl]acetamide
-
 ?
2.3.1.5 additional information results confirm that substituted anilines are excellent substrates and that TBNAT is ineffective in hydrazide N-acetylation Mycobacterium tuberculosis ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.5 arylamine N-acetyltransferase
-
 Mycobacterium tuberculosis
2.3.1.5 NAT
-
 Mycobacterium tuberculosis
2.3.1.5 TBNAT
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.5 25
-
 assay at Mycobacterium tuberculosis
2.3.1.5 25
-
 activity assay Mycobacterium tuberculosis

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.5 0.2
-
 4-chloroaniline
-
 Mycobacterium tuberculosis
2.3.1.5 0.28
-
 aniline
-
 Mycobacterium tuberculosis
2.3.1.5 0.6
-
 nicotinic acid hydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 0.7
-
 p-Aminobenzoic acid
-
 Mycobacterium tuberculosis
2.3.1.5 0.8
-
 4-methylaniline
-
 Mycobacterium tuberculosis
2.3.1.5 0.9
-
 4-fluoroaniline
-
 Mycobacterium tuberculosis
2.3.1.5 1.9
-
 benzoic acid hydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 2.9
-
 anisidine
-
 Mycobacterium tuberculosis
2.3.1.5 4.9
-
 isoniazid
-
 Mycobacterium tuberculosis
2.3.1.5 10.9
-
 4-hydroxybenzhydrazide
-
 Mycobacterium tuberculosis
2.3.1.5 21
-
 2-amino-4-chlorophenol
-
 Mycobacterium tuberculosis
2.3.1.5 44
-
 hydralazine
-
 Mycobacterium tuberculosis
2.3.1.5 51
-
 2-Aminophenol
-
 Mycobacterium tuberculosis
2.3.1.5 66
-
 4-amino-3-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.3.1.5 70
-
 2-amino-4-methylphenol
-
 Mycobacterium tuberculosis
2.3.1.5 94
-
 3-Amino-4-hydroxybenzoic acid
-
 Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.5 7.7
-
 assay at Mycobacterium tuberculosis
2.3.1.5 7.7
-
 activity assay Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
2.3.1.5 acetyl-CoA
-
 Mycobacterium tuberculosis