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Information on EC 1.3.1.98 - UDP-N-acetylmuramate dehydrogenase and Organism(s) Mycobacterium tuberculosis and UniProt Accession P9WJL9

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IUBMB Comments
A flavoprotein (FAD). NADH can to a lesser extent replace NADPH.
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Select one or more organisms in this record: ?
This record set is specific for:
Mycobacterium tuberculosis
UNIPROT: P9WJL9
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The taxonomic range for the selected organisms is: Mycobacterium tuberculosis
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
udp-n-acetylenolpyruvylglucosamine reductase, udp-n-acetylenolpyruvoylglucosamine reductase, murbab, udp-n-acetylenolpyruvyl glucosamine reductase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
EC 1.1.1.158
formerly
UDP-N-acetylenolpyruvoylglucosamine reductase
-
EC 1.1.1.158
-
formerly
reductase, uridine diphosphoacetylpyruvoylglucosamine
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-
-
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UDP-GlcNAc-enoylpyruvate reductase
-
-
-
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UDP-N-acetylenolpyruvoylglucosamine reductase
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-
-
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UDP-N-acetylenolpyruvylglucosamine reductase
-
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UDP-N-acetylglucosamine-enoylpyruvate reductase
-
-
-
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UDP-N-acetylmuramate dehydrogenase
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-
-
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uridine diphospho-N-acetylglucosamine-enolpyruvate reductase
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-
-
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uridine-5'-diphospho-N-acetyl-2-amino-2-deoxy-3-O-lactylglucose:NADP-oxidoreductase
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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-
-
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oxidation
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-
-
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reduction
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-
-
-
SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-alpha-D-muramate:NADP+ oxidoreductase
A flavoprotein (FAD). NADH can to a lesser extent replace NADPH.
CAS REGISTRY NUMBER
COMMENTARY hide
39307-28-3
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
show the reaction diagram
-
-
-
?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
show the reaction diagram
-
-
-
?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
show the reaction diagram
complex of MurB and substrate forms strong hydrogen bond with Arg176, Ser257 and Glu361. The secondary structure of MurB consists of 13 helices, 6 beta sheets, 6 beta hairpins, 5 beta bluges, 19 stands, 52 beta turns and 4 inverse gamma turns
-
-
?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
show the reaction diagram
-
-
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K+
-
required for activation
additional information
-
not influenced by Mg2+
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4S)-1,2-bis(4-chlorophenyl)-5-[2-(2,4-difluorophenyl)-2-oxoethoxy]-4-methylpyrazolidin-3-one
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1,2-bis(4-chlorophenyl)-4,4-bis(6-phenylhexyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4,4-bis[2-(2,4-difluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(2,4-dichlorobenzyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(2-ethylbutyl)pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-(2-phenylethyl)pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-(3-methoxybenzyl)pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-(3-oxo-3-phenylpropyl)pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-(3-phenylpropyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(4-oxo-4-phenylbutyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(4-phenylbutyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(5-phenylpentyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(6-phenylhexyl)pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-heptylpyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-[2-(2,4-difluorophenyl)-2-oxoethyl]-4-methylpyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-[2-(4-fluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-[2-(diethylamino)ethyl]pyrazolidine-3,5-dione
-
1,2-bis(4-chlorophenyl)-4-[3-(trifluoromethyl)benzyl]pyrazolidine-3,5-dione
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4'-[[1,2-bis(4-chlorophenyl)-3,5-dioxopyrazolidin-4-yl]methyl]biphenyl-2-carbonitrile
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4,4-bis[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-(2-chlorobenzyl)-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-benzyl-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)-4-methylpyrazolidine-3,5-dione
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4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[2-(benzylsulfanyl)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[2-[benzyl(ethyl)amino]ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[3,5-bis(trifluoromethyl)benzyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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Ca2+
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complete inhibition at 10 mM
guanidine hydrochloride
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an exponential decrease in enzymatic activity from 100% to 20% is observed between 0 and 0.05 M, no activity is observed above 0.5 M
Urea
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no activity at 2.5 M
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0425
NADPH
-
pH and temperature not specified in the publication
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000389
ZINC11839554
pH and temperature not specified in the publication
-
0.00002277
ZINC12242812
pH and temperature not specified in the publication
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0.00001281
ZINC14976552
pH and temperature not specified in the publication
-
0.00001453
ZINC14982226
pH and temperature not specified in the publication
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0.00001336
ZINC14995379
pH and temperature not specified in the publication
-
0.0000132
ZINC18122756
pH and temperature not specified in the publication
0.00000226
ZINC19837204
pH and temperature not specified in the publication
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
(4S)-1,2-bis(4-chlorophenyl)-5-[2-(2,4-difluorophenyl)-2-oxoethoxy]-4-methylpyrazolidin-3-one
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0072
1,2-bis(4-chlorophenyl)-4,4-bis(6-phenylhexyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0058
1,2-bis(4-chlorophenyl)-4,4-bis[2-(2,4-difluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.011
1,2-bis(4-chlorophenyl)-4-(2,4-dichlorobenzyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.05
1,2-bis(4-chlorophenyl)-4-(2-ethylbutyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.035 - 0.05
1,2-bis(4-chlorophenyl)-4-(2-phenylethyl)pyrazolidine-3,5-dione
0.05
1,2-bis(4-chlorophenyl)-4-(3-methoxybenzyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.013
1,2-bis(4-chlorophenyl)-4-(3-oxo-3-phenylpropyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.01
1,2-bis(4-chlorophenyl)-4-(3-phenylpropyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.01
1,2-bis(4-chlorophenyl)-4-(4-oxo-4-phenylbutyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0056
1,2-bis(4-chlorophenyl)-4-(4-phenylbutyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.01
1,2-bis(4-chlorophenyl)-4-(5-phenylpentyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0089
1,2-bis(4-chlorophenyl)-4-(6-phenylhexyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.042
1,2-bis(4-chlorophenyl)-4-heptylpyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.049
1,2-bis(4-chlorophenyl)-4-[2-(2,4-difluorophenyl)-2-oxoethyl]-4-methylpyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0054
1,2-bis(4-chlorophenyl)-4-[2-(4-fluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.05
1,2-bis(4-chlorophenyl)-4-[2-(diethylamino)ethyl]pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.018
1,2-bis(4-chlorophenyl)-4-[3-(trifluoromethyl)benzyl]pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.011
4'-[[1,2-bis(4-chlorophenyl)-3,5-dioxopyrazolidin-4-yl]methyl]biphenyl-2-carbonitrile
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0072
4,4-bis[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.05
4-(2-chlorobenzyl)-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.05
4-benzyl-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.02
4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)-4-methylpyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.011
4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.0052
4-[2-(benzylsulfanyl)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.05
4-[2-[benzyl(ethyl)amino]ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.012
4-[3,5-bis(trifluoromethyl)benzyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
Mycobacterium tuberculosis
pH and temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 40
-
at 20 and 40°C more than 85% of the activity is retained
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme catalyzes the final steps of the UDP-N-acetylmuramic acid formation in the peptidoglycan biosynthesis pathway
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
-
ESI mass spectrometry
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 40000, SDS-PAGE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme bound to FAD and K+, hanging drop vapor diffusion method
sequence alignment with Escherichia coli structures, PDB entries 2Q85 and 2MBR, and modeling of structure as well as docking with N-acetylpyruvyl glucosamine
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 10
-
any increase or decrease in pH from 8.0 results in significant drop in functional activity of the enzyme. Complete loss of activity occurs at pH 10.0
722410
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40 - 60
-
between 40°C and 60°C a fast decrease in enzyme activity is observed and above 60°C activity is completely lost
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA agarose column chromatography
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
computional design of 3-D structures of MurB enzymes and docking studies will provide highly useful information towards rational design of new tuberculosis drugs through experimental research design for further formulations as per pharmaceutical norms
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Babajan, B.; Anuradha, C.; Chaitanya, M.; Gowsia, D.; Kumar, C.
In silico structural characterization of Mycobacterium tuberculosis H37Rv UDP-N-acetylmuramate dehydrogenase
Int. J. Integr. Biol.
6
12-16
2009
Mycobacterium tuberculosis, Mycobacterium tuberculosis (B5AFK3), Mycobacterium tuberculosis H37Rv (B5AFK3)
-
Manually annotated by BRENDA team
Gautam, A.; Shukla, H.; Khan, S.; Rishi, P.; Bhakuni, V.; Tewari, R.
Structural and functional features of UDP-N-acetylenolpyruvylglucosamine reductase of Mycobacterium tuberculosis H37Rv
Int. J. Integr. Biol.
10
66-75
2010
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
-
Manually annotated by BRENDA team
Kumar, V.; Saravanan, P.; Arvind, A.; Mohan, C.G.
Identification of hotspot regions of MurB oxidoreductase enzyme using homology modeling, molecular dynamics and molecular docking techniques
J. Mol. Model.
17
939-953
2011
Mycobacterium tuberculosis (P9WJL9), Mycobacterium tuberculosis H37Rv (P9WJL9)
Manually annotated by BRENDA team
Isa, M.; Mohammed, M.
Molecular docking and dynamic simulation of UDP-N-acetylenolpyruvoylglucosamine reductase (MurB) obtained from Mycobacterium tuberculosis using in silico approach
Netw. Model. Anal. Health Inform. Bioinform.
10
40
2021
Mycobacterium tuberculosis (P9WJL9), Mycobacterium tuberculosis H37Rv (P9WJL9)
-
Manually annotated by BRENDA team