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EC Tree
The taxonomic range for the selected organisms is: Pseudomonas aeruginosa The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
alanine racemase,
alr-2 , d-alanine racemase, alrbax, mbalr2, alrtt, l-alanine racemase, alraba, cdalr, cbl/alr,
more
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L-Alanine racemase
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-
-
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L-Alanine:D-alanine racemase
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-
-
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Racemase, alanine
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-
-
-
ALR
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-
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alanine racemase
A pyridoxal-phosphate protein.
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L-alanine
D-alanine
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-
-
r
D-alanine
L-alanine
-
-
-
-
r
L-Ala
D-Ala
-
-
-
?
L-Ala
D-Ala
-
enzyme is required for production of D-Ala, a necessary component of the bacterial cell wall
-
?
L-alanine
D-alanine
-
-
-
-
r
L-alanine
D-alanine
-
-
-
r
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L-alanine
D-alanine
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-
-
r
L-Ala
D-Ala
-
enzyme is required for production of D-Ala, a necessary component of the bacterial cell wall
-
?
L-alanine
D-alanine
-
-
-
r
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pyridoxal 5'-phosphate
each monomer is comprised of two domains, an eight-stranded alpha/beta barrel containing the pyridoxal 5'-phosphate cofactor and a second domain primarily composed of beta-strands. The cofactor adopts two partially occupied conformational states that resemble previously reported and external aldimine complexes
pyridoxal 5'-phosphate
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-
pyridoxal 5'-phosphate
PLP, dependent on
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((6R)-2-carboxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl 3-chloro-D-alanyl-D-alaninate
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(2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate
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alafosfalin
selective inhibitor of peptidoglycan biosynthesis in both Grampositive and Gram-negative bacteria
beta-Chloro-D-alanine
90-95% inhibition
D-cycloserine
competitive inhibition, importance of N2-structural site in cyloserine for bioactivity
L-Cycloserine
competitive inhibition, importance of N2-structural site in cyloserine for bioactivity
L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide
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L-norvalyl-L-chlorovinylglycine
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[(1R)-1-amino-2-chloroethyl]phosphonic acid
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additional information
N2-substitution of carboxybenzyl-protected derivatives of DL-cycloserine proceed smoothly with the requisite alkyl halide in the presence of potassium tert-butoxide in dimethylformamide. The synthesised compounds are evaluated for their inhibitory activity against purified Alrs (Alr gene product). Structural modification at the N2 position result in reduced activity in the enzyme assay and underscore the importance of structural modification at N2-position of cycloserine. A compound with CH2CONHOCH3 substituent at (N)-2 position exhibits modest inhibitory activity against purified Alr enzyme from Escherichia coli, Ki is 0.47 mM. No inhibition by ((6R)-2-carboxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl 3-chloro-D-alanyl-3-chloro-D-alaninate
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1.1
D-Ala
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23°C, enzyme Alr
1.4
D-Ala
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23°C, enzyme DadX
4.2
D-alanine
-
in 50 mM potassium phosphate buffer pH 7.4, at 30°C
5.6
D-alanine
-
in 50 mM potassium phosphate buffer pH 7.4, at 30°C
1.1
L-Ala
-
23°C, enzyme Alr
1.4
L-Ala
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23°C, enzyme DadX
4.1
L-alanine
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in 50 mM potassium phosphate buffer pH 7.4, at 30°C
9.8
L-alanine
-
in 50 mM potassium phosphate buffer pH 7.4, at 30°C
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0.0138
D-cycloserine
pH and temperature not specified in the publication
0.0138
L-Cycloserine
pH and temperature not specified in the publication
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-
SwissProt
brenda
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metabolism
important for peptidoglycan biosynthesis
evolution
alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme. Pseudomonas aeruginosa has two isozymes, encoded by the Alr and the DadB genes
metabolism
DadB expression is induced by L-alanine to a level much greater than that of Alr and is probably responsible for the catabolism of D-Ala. Alr is constitutively expressed and seems to provide the D-alanine necessary to maintain cell growth
physiological function
D-alanine, produced by the action of alanine racemase on L-alanine, is important to both Gram-positive and Gram-negative bacteria, since it is required for the synthesis of the peptidoglycan in the cell wall
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38337
-
2 * 38337, calculated from amino acid sequence
39068
-
2 * 39068, calculated from amino acid sequence
40000
-
2 * 40000, SDS-PAGE
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dimer
each monomer is comprised of two domains, an eight-stranded alpha/beta barrel containing the pyridoxal 5'-phosphate cofactor and a second domain primarily composed of beta-strands
homodimer
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2 * 40000, SDS-PAGE
homodimer
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2 * 38337, calculated from amino acid sequence
homodimer
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2 * 39068, calculated from amino acid sequence
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sitting drops equilibrated versus 1.5 M (NH4)2SO4, 2% polyethylene glycol 400 and 0.1 M HEPES, pH 7.5, crystal strcuture at 1.45 A resolution
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recombinant enzymes Alr and DadX
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cloning of two independent alanine racemases in Escherichia coli: Alr and DadX
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expressed in Escherichia coli BL21(DE3) cells
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drug development
Alr is a target for the development of antibacterial drugs
medicine
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the requirement for D-Ala as a necessary component of the bacterial cell wall makes the enzyme a logical target for the development of novel antibiotics
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Lacoste, A.M.; Darriet, M.; Neuzil, E.; Le Goffic, F.
Inhibition of alanine racemase by vinylglycine and its phosphonic analogue: a 1H nuclear magnetic resonance spectroscopy study
Biochem. Soc. Trans.
16
606-608
1988
Pseudomonas aeruginosa, Pseudomonas aeruginosa A237
-
brenda
LeMagueres, P.; Im, H.; Dvorak, A.; Strych, U.; Benedik, M.; Krause, K.L.
Crystal structure at 1.45 A resolution of alanine racemase from a pathogenic bacterium, Pseudomonas aeruginosa, contains both internal and external aldimine forms
Biochemistry
42
14752-14761
2003
Pseudomonas aeruginosa (Q9HTQ2), Pseudomonas aeruginosa
brenda
Strych, U.; Huang, H.C.; Krause, K.L.; Benedik, M.J.
Characterization of the alanine racemases from Pseudomonas aeruginosa PAO1
Curr. Microbiol.
41
290-294
2000
Pseudomonas aeruginosa
brenda
Priyadarshi, A.; Lee, E.H.; Sung, M.W.; Nam, K.H.; Lee, W.H.; Kim, E.E.; Hwang, K.Y.
Structural insights into the alanine racemase from Enterococcus faecalis
Biochim. Biophys. Acta
1794
1030-1040
2009
Escherichia coli (P0A6B4), Geobacillus stearothermophilus (P10724), Haemophilus influenzae (P45257), Mycobacterium tuberculosis (P9WQA9), Helicobacter pylori (Q1XG01), Enterococcus faecalis v583 (Q837J0), Enterococcus faecalis v583, Pseudomonas aeruginosa (Q9HTQ2), Mycobacterium tuberculosis H37Rv (P9WQA9)
brenda
Ju, J.; Xu, S.; Furukawa, Y.; Zhang, Y.; Misono, H.; Minamino, T.; Namba, K.; Zhao, B.; Ohnishi, K.
Correlation between catalytic activity and monomer-dimer equilibrium of bacterial alanine racemases
J. Biochem.
149
83-89
2011
Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Pseudomonas fluorescens LRB3W1, Pseudomonas fluorescens TM5-2, Pseudomonas putida, Pseudomonas putida KT 2240, Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Azam, M.A.; Jayaram, U.
Inhibitors of alanine racemase enzyme a review
J. Enzyme Inhib. Med. Chem.
31
517-526
2016
Geobacillus stearothermophilus, Bacillus cereus, Chlamydia pneumoniae, Enterobacter sp., Enterococcus faecalis, Lactiplantibacillus plantarum, Lactococcus lactis, Listeria monocytogenes, Methanococcus maripaludis, Staphylococcus aureus, Mycobacterium tuberculosis, Mycolicibacterium smegmatis, no activity in Homo sapiens, Proteus mirabilis, Salmonella enterica subsp. enterica serovar Typhimurium, Serratia marcescens, Erysipelothrix rhusiopathiae, Escherichia coli (P0A6B4), Pseudomonas aeruginosa (Q9HUN4), Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 (Q9HUN4)
brenda