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2.3.1.157: glucosamine-1-phosphate N-acetyltransferase

This is an abbreviated version!
For detailed information about glucosamine-1-phosphate N-acetyltransferase, go to the full flat file.

Word Map on EC 2.3.1.157

Reaction

acetyl-CoA
+
alpha-D-glucosamine 1-phosphate
=
CoA
 +
N-acetyl-alpha-D-glucosamine 1-phosphate

Synonyms

amino-sugar-1-P AcTase, amino-sugar-1-phosphate acetyltransferase, bifunctional GlmU protein, bifunctional N-acetyltransferase/uridylyltransferase, bifunctional protein GlmU, bifunctional UDP-N-acetylglucosamine pyrophosphorylase/glucosamine-1-phosphate N-acetyltransferase, galactosamine-1-phosphate acetyltransferase, GalN-1-P AcTase, GlcN-1-P acetyltransferase, GlcN-1-P AcTase, GlcNAc-1-P uridyltransferase, GlmU, GlmU acetyltransferase, GlmU enzyme, GlmU uridyltransferase, glucosamine 1-phosphate N-acetyltransferase/N-acetylglucosamine-1-phosphate uridyltransferase, glucosamine-1-phosphate acetyltransferase, glucosamine-1-phosphate acetyltransferase/N-acetylglucosamine-1-phosphate uridyltransferase, More, MtbGlmU, MtGlmU, N-acetylglucosamine-1-phosphate pyrophosphorylase, N-acetylglucosamine-1-phosphate uridyltransferase, N-acetylglucosamine-1-phosphate-uridyltransferase/glucosamine-1-phosphate-acetyltransferase, N-acetylglucosamine-1-phosphate-uridylyltransferase/glucosamine-1-phosphate-acetyltransferase, Rv1018c, Rxn-1, ST0452, ST0452 protein, STK_04520, UDP-GlcNAc pyrophosphorylase, UDP-N-acetylglucosamine pyrophosphorylase/glucosamine-1-phosphate N-acetyltransferase

ECTree

     2 Transferases
         2.3 Acyltransferases
             2.3.1 Transferring groups other than aminoacyl groups
                2.3.1.157 glucosamine-1-phosphate N-acetyltransferase

Inhibitors

Inhibitors on EC 2.3.1.157 - glucosamine-1-phosphate N-acetyltransferase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2R)-2-[[2,4-dimethoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]carbamoyl]-3-methylcyclopropanecarboxylic acid
(1R,2R)-2-[[4-hydroxy-2-methoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]carbamoyl]-3-methylcyclopropanecarboxylic acid
(1R,2R)-2-[[5-(acridin-10(9H)-ylsulfonyl)-2,4-dimethoxyphenyl]carbamoyl]-3-methylcyclopropanecarboxylic acid
(1R,2R)-2-[[5-(acridin-10(9H)-ylsulfonyl)-4-hydroxy-2-methoxyphenyl]carbamoyl]-3-methylcyclopropanecarboxylic acid
(2E)-4-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-4-oxobut-2-enoic acid
(2E)-4-[[2,4-dimethoxy-5-(10H-phenoxazin-10-ylsulfonyl)phenyl]amino]-4-oxobut-2-enoic acid
-
(4Z)-4-(4-benzyloxybenzylidene)-2-(naphthalen-2-yl)-1,3-oxazol-5(4H)-one
a oxazolidine derivative that specifically inhibits GlmU. Administration to infected mice results in significant decrease in the bacillary load
(5-[(E)-[(2,5-dimethylphenyl)imino]methyl]furan-2-yl)(hydroxy)oxoammonium
(5E)-1-(3,5-dimethylphenyl)-5-(furan-2-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
uncompetitive versus acetyl-CoA and alpha-D-glucosamine 1-phosphate, inhibits GlmU enzyme acetyltransferase activity
(5Z)-2-imino-5-[(2E)-3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]-1,3-thiazolidin-4-one
competitive versus acetyl-CoA, uncompetitive versus alpha-D-glucosamine 1-phosphate, specificly inhibits GlmU acetyltransferase activity and also exhibits whole cell activity against drug susceptible as well as drug resistant Mycobacterium tuberculosis. The compound also exhibits increased anti-tuberculois activity when tested in combination with rifampicin, isoniazid and ethambutol, but is cytotoxxic for the eukaryotic cell line; specific inhibition of acetyltransferase activity, competitive with respect to acetyl-CoA. Compound also exhibits whole cell activity against drug susceptible as well as drug resistant Mycobacterium tuberculosis and increased anti-TB activity when tested in combination with rifampicin, isoniazid and ethambutol. Compound is cytotoxic to eukaryotic cell line
(5Z)-5-(furan-3-ylmethylidene)-1-(4-methoxyphenyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
uncompetitive versus acetyl-CoA and alpha-D-glucosamine 1-phosphate, inhibits GlmU enzyme acetyltransferase activity
(E)-N-(2,5-dimethylphenyl)-1-(5-nitrofuran-2-yl)methanimine
(E)-N-(2-fluoro-5-nitrophenyl)-1-(5-nitrofuran-2-yl)methanimine
1-(2-[[([5-[(3-carboxypropanoyl)amino]-2,4-dimethoxyphenyl]sulfonyl)amino]methyl]phenyl)piperidine-4-carboxylic acid
1-butyl-2-[(E)-2-(5-nitrofuran-2-yl)ethenyl]-1H-benzimidazole
unspecific inhibitor, 84.26% inhibition at 0.1 mM
1-[2,4-dimethoxy-5-(10H-phenoxazin-10-ylsulfonyl)phenylamino]-2-(-4-pyridyl)-1-ethanone
1-[2,4-dimethoxy-5-(10H-phenoxazin-10-ylsulfonyl)phenylamino]-2-(4-pyridyl)-1-ethanone
2'-[[([5-[(3-carboxypropanoyl)amino]-2,4-dimethoxyphenyl]sulfonyl)amino]methyl]biphenyl-4-carboxylic acid
2-(2-cyanopyridin-4-yl)-N-[2,4-dimethoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]acetamide
2-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-2-oxoethyl acetate
2-amino-2,3-dideoxy-3-fluoro-alpha-D-glucopyranosyl phosphate
-
-
2-nitro-5-thiocyanatobenzoic acid
-
0.5 mM, 5% residual activity
2-Nitro-5-thiocyanobenzoic acid
-
-
3-fluoro-N-[1-(2-methylpropanoyl)-1,2,3,4-tetrahydroquinolin-6-yl]benzene-1-sulfonamide
3-fluoro-N-[1-(2-methylpropanoyl)-1,2,3,4-tetrahydroquinolin-6-yl]benzenesulfonamide
3-hydrazinylquinoline-2-thiol
3-[(2,4-dimethoxyphenyl)amino]-4-phenylcyclobut-3-ene-1,2-dione
40.0% inhibition at 0.1 mM
4-(4-(benzyloxy)benzylidene)-2-(naphthalen-1-yl)oxazol-5(4H)-one
i.e. Oxa33, syntesis of a specific GlmU inhibitor, molecular docking study, the inhibitor binds to an allosteric site of the uridyltransferase domain., overview. Oxa33 fails to inhibit cell growth even at concentrations as high as 0.150 mM
4-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-4-oxobutanoic acid
4-([2,4-dimethoxy-5-[naphthalen-2-yl(phenyl)sulfamoyl]phenyl]amino)-4-oxobutanoic acid
4-([4-hydroxy-2-methoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-4-oxobutanoic acid
4-([5-[(4-aminophenyl)(phenyl)sulfamoyl]-2,4-dimethoxyphenyl]amino)-4-oxobutanoic acid
4-([5-[bis(4-methylphenyl)sulfamoyl]-2,4-dimethoxyphenyl]amino)-4-oxobutanoic acid
4-[(2,4-dimethoxy-5-[[2-(piperidin-1-yl)benzyl]sulfamoyl]phenyl)amino]-4-oxobutanoic acid
4-[(5-[[2-(4-[[(carboxyacetyl)oxy]methyl]piperidin-1-yl)benzyl]sulfamoyl]-2,4-dimethoxyphenyl)amino]-4-oxobutanoic acid
4-[2-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-2-oxoethoxy]benzoic acid
4-[[(2,6-dimethoxybenzoyl)oxy]imino]cyclohexa-2,5-dien-1-one
competitive versus acetyl-CoA, noncompetitive versus alpha-D-glucosamine 1-phosphate, specificly inhibits GlmU acetyltransferase activity and also exhibits whole cell activity against drug susceptible as well as drug resistant Mycobacterium tuberculosis. The compound also exhibits increased anti-tuberculois activity when tested in combination with rifampicin, isoniazid and ethambutol; specific inhibition of acetyltransferase activity, competitive with respect to acetyl-CoA. Compound also exhibits whole cell activity against drug susceptible as well as drug resistant Mycobacterium tuberculosis and increased anti-TB activity when tested in combination with rifampicin, isoniazid and ethambutol
4-[[2,4-dimethoxy-5-(10H-phenothiazin-10-ylsulfonyl)phenyl]amino]-4-oxobutanoic acid
4-[[2,4-dimethoxy-5-(10H-phenoxazin-10-ylsulfonyl)phenyl]amino]-4-oxobutanoic acid
4-[[4-hydroxy-2-methoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]amino]-4-oxobutanoic acid
4-[[5-(dibenzo[b,f][1,4]oxazepin-10(11H)-ylsulfonyl)-2,4-dimethoxyphenyl]amino]-4-oxobutanoic acid
4-[[5-(diphenylsulfamoyl)-2,4-dimethoxyphenyl]amino]-4-oxobutanoic acid
4-[[5-([2-[4-(carboxymethyl)piperidin-1-yl]benzyl]sulfamoyl)-2,4-dimethoxyphenyl]amino]-4-oxobutanoic acid
4-[[5-([2-[4-(hydroxymethyl)piperidin-1-yl]benzyl]sulfamoyl)-2,4-dimethoxyphenyl]amino]-4-oxobutanoic acid
5,5'-dithiobis-(2-nitrobenzoic acid)
-
0.1 mM, 33% residual activity
5,7-dichloro-2-hydrazinylquinolin-8-ol
5-(1,2-oxazol-5-yl)-N-(pyridin-3-ylmethyl)furan-2-sulfonamide
44.7% inhibition at 0.1 mM
6-chloro-N-[3-(methylsulfanyl)phenyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide
alpha-D-glucosamine 1-phosphate
-
substrate inhibition, competitive versus N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]acetamide
Ca2+
2 mM, inhibits D-glucosamine-1-phosphate N-acetyltransferase activity
Co2+
2 mM, inhibits D-glucosamine-1-phosphate N-acetyltransferase activity
D-galactosamine 1-phosphate
-
D-glucosamine 6-phosphate
-
D-glucose 1-phosphate
-
dicumarol
uncompetitively inhibits acetyl CoA and shows mixed-type inhibition for glucosamine-1-phosphate. Dicumarol also exhibits inhibitory effects on several clinically sensitive Mycobacterium tuberculosis strains and drug-resistant strains, with a range of MIC value of 6.25 to more than 100 mg/ml. Dicumarol increases the sensitivity of anti-tuberculosis drugs (isoniazid and rifampicin) when dicumarol is present at a low concentration
ethyl (2-[(Z)-[2-(ethylsulfanyl)-5-oxo-1,3-thiazol-4(5H)-ylidene]methyl]phenoxy)acetate
45.3% inhibition at 0.1 mM
iodoacetamide
-
-
methyl 2-[([[5-(acetylamino)-2,4-dimethoxyphenyl]sulfonyl]amino)methyl]benzoate
Mg2+
2 mM, inhibits D-glucosamine-1-phosphate N-acetyltransferase activity
Mn2+
2 mM, inhibits D-glucosamine-1-phosphate N-acetyltransferase activity
N-(2,4-dimethoxy-5-[[2-(piperidin-1-yl)benzyl]sulfamoyl]phenyl)acetamide
N-(2,5-dimethoxyphenyl)-N-(phenylsulfonyl)glycine
42.01% inhibition at 0.1 mM
-
N-(3-chlorophenyl)-2-methoxy-5-(2-methyl-1,3-oxazol-5-yl)benzenesulfonamide
406% inhibition at 0.1 mM
N-(5-chloro-2-methoxyphenyl)-N-(phenylsulfonyl)glycine
45.15% inhibition at 0.1 mM
N-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]carbamothioyl)glycine
N-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]carbamoyl)glycine
N-acetylglucosamine-1-phosphate
-
acetyltransferase activity inhibited by its reaction product
N-ethylmaleimide
-
-
N-[2,4-dimethoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]-2-(2-fluoropyridin-4-yl)acetamide
N-[2,4-dimethoxy-5-(1,2,3,4-tetrahydroquinolin-2-ylsulfonyl)phenyl]-3-(2H-tetrazol-5-yl)propanamide
N-[2,4-dimethoxy-5-(10H-phenoxazin-10-ylsulfonyl)phenyl]-2-(pyridin-4-yl)acetamide
-
N-[2,4-dimethoxy-5-(10H-phenoxazine-10-sulfonyl)phenyl]-2-(pyridin-4-yl)acetamide
N-[2,4-dimethoxy-5-(phenylsulfamoyl)phenyl]acetamide
N-[2,4-dimethoxy-5-(piperidin-1-ylsulfonyl)phenyl]acetamide
N-[2,4-dimethoxy-5-[(2-methoxybenzyl)sulfamoyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[(2-methyl-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]-2-(pyridin-4-ylsulfanyl)acetamide
N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]benzamide
N-[2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]methanesulfonamide
N-[2,4-dimethoxy-5-[(2-methylpyrrolidin-1-yl)sulfonyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[(3-methylphenyl)sulfamoyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[(4-methylphenyl)sulfamoyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[methyl(phenyl)sulfamoyl]phenyl]acetamide
N-[2,4-dimethoxy-5-[phenyl(propan-2-yl)sulfamoyl]phenyl]acetamide
N-[5-(acridin-10(9H)-ylsulfonyl)-2,4-dimethoxyphenyl]-2-(2-fluoropyridin-4-yl)acetamide
N-[5-(acridin-10(9H)-ylsulfonyl)-2,4-dimethoxyphenyl]-2-(pyridin-4-yl)acetamide
N-[5-(dimethylsulfamoyl)-2,4-dimethoxyphenyl]acetamide
N-[5-([2-[4-(hydroxymethyl)piperidin-1-yl]benzyl]sulfamoyl)-2,4-dimethoxyphenyl]acetamide
N-[5-[(1,3-benzodioxol-5-ylmethyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[(2-bromobenzyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[(2-fluorophenyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[(3-fluorophenyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[(4-fluorophenyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[butyl(propan-2-yl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
N-[5-[ethyl(2-methylphenyl)sulfamoyl]-2,4-dimethoxyphenyl]acetamide
p-hydroxymercuribenzoate
-
-
terreic acid
UDP-MurNAc
-
1 mM, relative enzyme activity 2%
Zn2+
2 mM, inhibits D-glucosamine-1-phosphate N-acetyltransferase activity
[2-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-2-oxoethoxy]acetic acid
[4-fluoro-3-[(E)-([5-[hydroxy(oxo)azaniumyl]furan-2-yl]methylidene)amino]phenyl](hydroxy)oxoammonium
[5-[(E)-2-(1-butyl-1H-benzimidazol-2-yl)ethenyl]furan-2-yl](hydroxy)oxoammonium
[[2-([2,4-dimethoxy-5-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)sulfonyl]phenyl]amino)-2-oxoethyl]sulfanyl]acetic acid
additional information
-