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Information on EC 5.1.1.3 - glutamate racemase and Organism(s) Enterococcus faecalis and UniProt Accession Q836J0

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EC Tree
     5 Isomerases
         5.1 Racemases and epimerases
             5.1.1 Acting on amino acids and derivatives
                5.1.1.3 glutamate racemase
IUBMB Comments
A pyridoxal-phosphate protein.
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Select one or more organisms in this record: ?
This record set is specific for:
Enterococcus faecalis
UNIPROT: Q836J0
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The taxonomic range for the selected organisms is: Enterococcus faecalis
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
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L-glutamate
=
D-glutamate
=
Synonyms
glutamate racemase, race2, race1, d-glutamate racemase, glutamic acid racemases, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glutamate racemase
-
-
Racemase, glutamate
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
racemization
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
glutamate racemase
A pyridoxal-phosphate protein.
CAS REGISTRY NUMBER
COMMENTARY hide
9024-08-2
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-glutamate
D-glutamate
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
L-glutamate
D-glutamate
show the reaction diagram
-
-
-
-
r
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-(butylsulfanyl)-9-(2-methoxy-5-nitrobenzyl)-9H-purin-6-amine
comparison with effect on Enterococcus faecium and Staphylococcus aureus
2-(butylsulfanyl)-9-(3-chloro-2,6-difluorobenzyl)-9H-purin-6-amine
comparison with effect on Enterococcus faecium and Staphylococcus aureus
2-butoxy-9-(3-chloro-2,6-difluorobenzyl)-N-(pyridin-3-ylmethyl)-9H-purin-6-amine
comparison with effect on Enterococcus faecium and Staphylococcus aureus
9-(2,6-difluoro-3-methylbenzyl)-2-[(1,1,1,2,2-pentafluoropentan-3-yl)oxy]-9H-purin-6-amine
comparison with effect on Enterococcus faecium and Staphylococcus aureus
(R,S)-1-hydroxy-1-oxo-4-amino-4-carboxyphosphorinane
-
-
(R,S)-4-amino-4-carboxy-1,1-dioxotetrahydro-thiopyran
-
-
1,1-dioxo-tetrahydrothiopyran-4-one
-
-
1-hydroxyphosphinan-4-one 1-oxide
-
-
2-(butylsulfanyl)-8-(4-fluorobenzyl)-4-(methylamino)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
2-(butylsulfanyl)-9-(4-nitrophenyl)-9H-purin-6-amine
-
comparison with effect on enzyme from Staphylococcus aureus
2-amino-4-phosphonobutanoic acid
-
-
4-amino-2-(butylsulfanyl)-8-(2,6-difluorobenzyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
4-amino-2-(butylsulfanyl)-8-(3,4-dichlorobenzyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
4-amino-2-(butylsulfanyl)-8-(4-fluorobenzyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
4-amino-8-benzyl-2-(benzylsulfanyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
4-amino-8-benzyl-2-(butylsulfanyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
4-amino-8-benzyl-2-(cyclopentylsulfanyl)-5,8-dihydropteridine-6,7-dione
-
comparison with effect on enzyme from Staphylococcus aureus
bis(2-carboxyethyl)-phosphinic acid
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
in contrast to Escherichia coli no activation by UDP-MurNAc-Ala, the product of the preceding enzyme in the peptidoglycan biosynthetic pathway
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.25
D-glutamate
-
-
1.2
L-glutamate
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.41 - 11.73
D-glutamate
25
L-glutamate
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.1
(R,S)-1-hydroxy-1-oxo-4-amino-4-carboxyphosphorinane
-
pH and temperature not specified in the publication
18.4
1,1-dioxo-tetrahydrothiopyran-4-one
-
pH and temperature not specified in the publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0014
2-(butylsulfanyl)-9-(2-methoxy-5-nitrobenzyl)-9H-purin-6-amine
Enterococcus faecalis
-
0.0022
2-(butylsulfanyl)-9-(3-chloro-2,6-difluorobenzyl)-9H-purin-6-amine
Enterococcus faecalis
-
0.002
2-butoxy-9-(3-chloro-2,6-difluorobenzyl)-N-(pyridin-3-ylmethyl)-9H-purin-6-amine
Enterococcus faecalis
-
0.0043
9-(2,6-difluoro-3-methylbenzyl)-2-[(1,1,1,2,2-pentafluoropentan-3-yl)oxy]-9H-purin-6-amine
Enterococcus faecalis
-
24.1
(R,S)-1-hydroxy-1-oxo-4-amino-4-carboxyphosphorinane
Enterococcus faecalis
-
pH and temperature not specified in the publication
215
(R,S)-4-amino-4-carboxy-1,1-dioxotetrahydro-thiopyran
Enterococcus faecalis
-
pH and temperature not specified in the publication
21.2
1,1-dioxo-tetrahydrothiopyran-4-one
Enterococcus faecalis
-
pH and temperature not specified in the publication
47.7
1-hydroxyphosphinan-4-one 1-oxide
Enterococcus faecalis
-
pH and temperature not specified in the publication
0.0009
2-(butylsulfanyl)-8-(4-fluorobenzyl)-4-(methylamino)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.007
2-(butylsulfanyl)-9-(4-nitrophenyl)-9H-purin-6-amine
Enterococcus faecalis
-
-
105
2-amino-4-phosphonobutanoic acid
Enterococcus faecalis
-
pH and temperature not specified in the publication
0.0015
4-amino-2-(butylsulfanyl)-8-(2,6-difluorobenzyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.00065
4-amino-2-(butylsulfanyl)-8-(3,4-dichlorobenzyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.0035
4-amino-2-(butylsulfanyl)-8-(4-fluorobenzyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.021
4-amino-8-benzyl-2-(benzylsulfanyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.0024
4-amino-8-benzyl-2-(butylsulfanyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
0.0019
4-amino-8-benzyl-2-(cyclopentylsulfanyl)-5,8-dihydropteridine-6,7-dione
Enterococcus faecalis
-
-
60.4
bis(2-carboxyethyl)-phosphinic acid
Enterococcus faecalis
-
pH and temperature not specified in the publication
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
D-glutamate is an essential biosynthetic building block of the peptidoglycans that encapsulate the bacterial cell wall
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
gel filtration
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
in complex with 9-benzyl purine inhibitors
crystal structures of MurI of Helicobacter pylori, Escherichia coli, Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium are analysed under similar, physiologically relevant conditons. MurI of Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium all form homodimeric structures. In all these structures, monomers oligomerize in a tail-to-tail orientation with active sites opposed and fully exposed to solvent
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme is purified by using standard chromatographic methods
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
full-length MurI proteins are prepared by expression either as native (Helicobacter pylori, Escherichia coli) or N-terminal 6xHis-tagged (Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium) recombinant proteins in Escherichia coli strains co-expressing the chaperone proteins GroEL/GroES27 and purified by standard chromatographic methods
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
glutamate racemase is an enzyme essential to the bacterial cell wall biosynthesis pathway, and is therefore considered as a target for antibacterial drug discovery
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lundqvist, T.; Fisher, S.L.; Kern, G.; Folmer, R.H.; Xue, Y.; Newton, D.T.; Keating, T.A.; Alm, R.A.; de Jonge, B.L.
Exploitation of structural and regulatory diversity in glutamate racemases
Nature
447
817-822
2007
Enterococcus faecalis, Enterococcus faecium, Escherichia coli, Helicobacter pylori, Staphylococcus aureus
Manually annotated by BRENDA team
Geng, B.; Breault, G.; Comita-Prevoir, J.; Petrichko, R.; Eyermann, C.; Lundqvist, T.; Doig, P.; Gorseth, E.; Noonan, B.
Exploring 9-benzyl purines as inhibitors of glutamate racemase (MurI) in Gram-positive bacteria
Bioorg. Med. Chem. Lett.
18
4368-4372
2008
Enterococcus faecalis (Q836J0), Enterococcus faecium (Q836J0)
Manually annotated by BRENDA team
Breault, G.A.; Comita-Prevoir, J.; Eyermann, C.J.; Geng, B.; Petrichko, R.; Doig, P.; Gorseth, E.; Noonan, B.
Exploring 8-benzyl pteridine-6,7-diones as inhibitors of glutamate racemase (MurI) in gram-positive bacteria
Bioorg. Med. Chem. Lett.
18
6100-6103
2008
Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus
Manually annotated by BRENDA team
Pal, M.; Bearne, S.L.
Inhibition of glutamate racemase by substrate-product analogues
Bioorg. Med. Chem. Lett.
24
1432-1436
2014
Enterococcus faecalis
Manually annotated by BRENDA team