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6.3.2.8: UDP-N-acetylmuramate-L-alanine ligase

This is an abbreviated version!
For detailed information about UDP-N-acetylmuramate-L-alanine ligase, go to the full flat file.

Word Map on EC 6.3.2.8

Reaction

ATP
+
UDP-N-acetyl-alpha-D-muramate
 +
L-alanine
=
ADP
 +
phosphate
 +
UDP-N-acetyl-alpha-D-muramoyl-L-alanine

Synonyms

Alanine-adding enzyme, alr5065, L-Ala ligase, L-Alanine adding enzyme, Mur ligase, MurB/CVs, MurC, MurC ligase, MurC synthetase, Synthetase, uridine diphospho-N-acetylmuramoylalanine, UDP-acetylmuramoyl-L-alanine synthetase, UDP-MurNAc:L-Ala ligase, UDP-MurNAc:L-alanine ligase, UDP-N-acetylenolpyruvoylglucosamine reductase/UDP-N-acetylmuramate: L-alanine ligase, UDP-N-acetylmuramate-alanine ligase, UDP-N-acetylmuramate:L-alanine ligase, UDP-N-acetylmuramic acid L-alanine ligase, UDP-N-acetylmuramoyl-L-alanine synthetase, UDP-N-acetylmuramoyl:L-alanine ligase, UDP-N-acetylmuramoylalanine synthetase, UDP-N-acetylmuramyl:L-alanine ligase, UNAM:Ala ligase, Uridine 5´-diphosphate-N-acetylmuramyl-L-alanine synthetase, Uridine diphosphate N-acetylmuramate:L-alanine ligase, Uridine diphospho-N-acetylmuramoylalanine synthetase, Uridine-diphosphate-N-acetylmuramate:L-alanine ligase

ECTree

     6 Ligases
         6.3 Forming carbon-nitrogen bonds
             6.3.2 Acid—amino-acid ligases (peptide synthases)
                6.3.2.8 UDP-N-acetylmuramate-L-alanine ligase

Inhibitors

Inhibitors on EC 6.3.2.8 - UDP-N-acetylmuramate-L-alanine ligase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]piperidin-2-yl)methanol
(1R,2S)-1-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2,3-dihydro-1H-inden-2-ol
(2R)-2-((4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3-cyclohexylpropan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(2-methoxypyridin-4-yl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(3-chloropyridin-4-yl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(3-fluorophenyl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(3-methyl-1,2-oxazol-5-yl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(4-methoxyphenyl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(pyridin-2-yl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(pyridin-3-yl)ethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-cyclohexylethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethan-1-ol
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl (2-aminoethyl)carbamate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl (2-hydroxyethyl)carbamate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl (2R)-2-(aminomethyl)morpholine-4-carboxylate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl hydroxycarbamate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl [(1,5-dihydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl [2-(3-oxopyrazolidin-1-yl)ethyl]carbamate
(2R)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethyl [[(4S)-3-methyl-2-oxoimidazolidin-4-yl]methyl]carbamate
(2R)-2-([4-[(5-tert-butyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-cyclohexylethan-1-ol
(2R)-2-cyclohexyl-2-[(4-[[5-(propan-2-yl)-1H-pyrazol-3-yl]amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]ethan-1-ol
(2S)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-cyclohexylethan-1-ol
(2S)-2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-phenylethan-1-ol
(2S)-2-cyclohexyl-2-([4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)ethan-1-ol
(2S)-2-cyclohexyl-2-[(4-[[5-(propan-2-yl)-1H-pyrazol-3-yl]amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]ethan-1-ol
(5Z)-5-([2-[(4-chlorobenzyl)sulfanyl]-5-nitrophenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
-
-
(5Z)-5-([4-[(E)-2-phenylethenyl]phenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
-
-
1H-indazole-3-carbohydrazide
-
-
2-((4-[(2S)-butan-2-ylamino]-6-(ethylamino)-1,3,5-triazin-2-yl)sulfanyl)-N-(2-chlorophenyl)acetamide
0.5 mM, 26% inhibition
2-(4-{[(E)-2-(1H-indazol-3-ylcarbonyl)hydrazono]methyl} phenoxy) acetic acid
-
complete inhibition at 0.5 mM
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 2-nitrobenzenesulfonate
-
55% inhibition at 0.05 mM
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 3-nitrobenzenesulfonate
-
65% inhibition at 0.05 mM
2-([2-(2-naphthylsulfonyl)hydrazono)methyl]phenyl 4-nitrobenzenesulfonate
-
75% inhibition at 0.10 mM
2-([2-(naphthalen-2-ylsulfonyl)hydrazono]methyl)phenyl 2-(benzo[d][1,3]dioxol-5-yl)acetate
-
57% inhibition at 0.10 mM
2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-2-(oxan-4-yl)ethan-1-ol
2-([4-[(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)amino]-1H-pyrazolo[3,4-d]pyrimidin-6-yl]amino)-3-methylbutan-1-ol
2-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
41% inhibition at 0.10 mM
2-phenyl-1,3-thiazole-5-carbohydrazide
-
-
2-phenyl-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazole-5-carbohydrazide
-
18% inhibition at 0.25 mM
2-[4-({(E)-2-[(4-methyl-1,3-thiazol-5-yl)carbonyl]hydrazono} methyl)phenoxy]acetic acid
-
complete inhibition at 0.5 mM
3,3,3-Trifluoro-DL-Ala
-
-
3,3-Difluoro-L-Ala
-
-
3-bromo-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
-
3-chloro-L-Ala
-
-
3-Cyano-L-Ala
-
-
3-Fluoro-L-Ala
-
-
4-([(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl)-6-(naphthalen-2-ylmethyl)-1,3,5-triazin-2-amine
0.5 mM, 30% inhibition
4-({(E)-2-[(4-methyl-1,3-thiazol-5-yl)carbonyl]hydrazono} methyl)benzoic acid
-
94% inhibition at 0.5 mM
4-cyano-N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
91% inhibition at 0.05 mM
4-methyl-1,3-thiazole-5-carbohydrazide
-
-
4-methyl-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazole-5-carbohydrazide
-
26% inhibition at 0.5 mM
4-methyl-N'-[(E)-(2-phenyl-1,3-thiazol-4-yl)methylidene]-1,3-thiazole-5-carbohydrazide
-
complete inhibition at 0.5 mM
4-{[(E)-2-(1H-indazol-3-ylcarbonyl)hydrazono]methyl}benzoic acid
-
complete inhibition at 0.5 mM
5-methyl-N-([4-(5-phenyl-1-benzofuran-2-yl)phenyl]sulfonyl)thiophene-2-carboxamide
-
IC50 2.3 microM
6-([(1,1-dioxidotetrahydrothiophen-3-yl)sulfanyl]methyl)-N-(2-phenylethyl)-1,3,5-triazine-2,4-diamine
0.25 mM, 32% inhibition
6-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-N,N'-diphenyl-1,3,5-triazine-2,4-diamine
0.5 mM, 36% inhibition
Ba2+
-
inhibits activation by Mn2+
benzohydrazide
-
-
benzylidene rhodanines
-
possess MurC inhibitory activity in the low micromolar range
-
beta-gamma-methyleneadenosine 5'-triphosphate
-
-
Cd2+
-
inhibits activation by Mn2+
Co2+
-
inhibits activation by Mn2+
Fe2+
-
inhibits activation by Mn2+
feglymycin
Hg2+
-
inhibits activation by Mn2+
KCl
-
inhibition above 100 mM
L-2-aminobutyrate
-
-
L-Ala-L-1-aminoethylphosphinic acid
-
i.e. alaphosphin
L-Allylglycine
-
weak
L-Cys
-
weak
L-lactate
-
-
L-propargylglycine
-
-
L-Ser
L-Vinylglycine
-
-
methyl4-({(E)-2-[(4-methyl-1,3-thiazol-5-yl)carbonyl]hydrazono}methyl)benzoate
-
95% inhibition at 0.5 mM
methyl4-{[(E)-2-(1H-indazol-3-ylcarbonyl)hydrazono]methyl} benzoate
-
complete inhibition at 0.5 mM
Mg2+
-
inhibits activation by Mn2+
N'-((2-[(2-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
30% inhibition at 0.10 mM
N'-((2-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
36% inhibition at 0.05 mM
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(2-fluorophenyl)methanesulfonohydrazide
-
59% inhibition at 0.10 mM
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)(phenyl)methanesulfonohydrazide
-
complete inhibition at 0.10 mM
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
36% inhibition at 0.10 mM
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-2-nitrobenzenesulfonohydrazide
-
95% inhibition at 0.01 mM
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)-3-nitrobenzenesulfonohydrazide
-
-
N'-((2-[(4-cyanobenzyl)oxy]phenyl)methylidene)[4-(trifluoromethyl)phenyl]methanesulfonohydrazide
-
-
N'-((3-[(3-nitrobenzyl)oxy]phenyl)methylidene)-2-naphthalenesulfonohydrazide
-
58% inhibition at 0.05 mM
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
42% inhibition at 0.25 mM
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
64% inhibition at 0.10 mM
N'-[(E)-(2,4-dihydroxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
74% inhibition at 0.25 mM
N'-[(E)-(2-hydroxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
complete inhibition at 0.25 mM
N'-[(E)-(2-phenyl-1,3-thiazol-4-yl)methylidene]-1H-indazole-3-carbohydrazide
-
78% inhibition at 0.10 mM
N'-[(E)-(2-phenyl-1,3-thiazol-4-yl)methylidene]benzohydrazide
-
70% inhibition at 0.25 mM
N'-[(E)-(3,4-dihydroxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
36% inhibition at 0.5 mM
N'-[(E)-(3,4-dihydroxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide
-
95% inhibition at 0.5 mM
N'-[(E)-(3,4-dihydroxyphenyl)methylidene]benzohydrazide
-
complete inhibition at 0.5 mM
N'-[(E)-(3,4-dimethoxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
complete inhibition at 0.5 mM
N'-[(E)-(3,4-dimethoxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide
-
complete inhibition at 0.5 mM
N'-[(E)-(3,4-dimethoxyphenyl)methylidene]benzohydrazide
-
97% inhibition at 0.5 mM
N'-[(E)-(3,5-dichloro-2-hydroxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide
-
43% inhibition at 0.25 mM
N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene] benzohydrazide
-
92% inhibition at 0.5 mM
N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-1H-indazole-3-carbohydrazide
-
67% inhibition at 0.25 mM
N'-[(E)-(4-cyanophenyl)methylidene]-1H-indazole-3-carbohydrazide
-
complete inhibition at 0.25 mM
N'-[(E)-(4-cyanophenyl)methylidene]benzohydrazide
-
complete inhibition at 0.25 mM
N'-[(E)-(4-nitrophenyl)methylidene]-1H-indazole-3-carbohydrazide
-
91% inhibition at 0.5 mM
N'-[(E)-1H-indol-3-ylmethylidene]-1H-indazole-3-carbohydrazide
-
complete inhibition at 010 mM
N'-[(E)-1H-indol-3-ylmethylidene]benzohydrazide
-
93% inhibition at 0.5 mM
N'-{(E)-[4-(dimethylamino)phenyl]methylidene}-1H-indazole-3-carbohydrazide
-
95% inhibition at 0.25 mM
N'-{(E)-[4-(dimethylamino)phenyl]methylidene}-4-methyl-1,3-thiazole-5-carbohydrazide
-
97% inhibition at 0.25 mM
N'-{(E)-[4-(dimethylamino)phenyl]methylidene}benzohydrazide
-
complete inhibition at 0.25 mM
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
-
51% inhibition at 0.10 mM
N-(2-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
-
-
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-naphthamide
-
-
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-2-nitrobenzamide
-
-
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-3,5-dinitrobenzamide
-
72% inhibition at 0.10 mM
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)-4-nitrobenzamide
-
71% inhibition at 0.05 mM
N-(4-([2-(2-naphthylsulfonyl)hydrazono]methyl)phenyl)benzamide
-
97% inhibition at 0.10 mM
N-Methyl-L-Ala
-
weak
N-[(E)-(2,4-dihydroxyphenyl)methylidene]benzohydrazide
-
complete inhibition at 0.5 mM
NaCl
-
inhibition above 100 mM
p-hydroxymercuribenzoate
-
partial protection by ATP
potassium phosphate
-
no effect up to 20 mM, significant decrease of activity at higher concentrations
UDP-2-(acetylamino)-4-O-[[(2-carboxypropyl)(hydroxy)phosphoryl]methyl]-2-deoxy-alpha-D-glucopyranose
-
-
UDP-N-acetylmuramoyl-L-Ala
-
-
additional information
-