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Literature summary extracted from
- Inhibitors of alanine racemase enzyme a review (2016), J. Enzyme Inhib. Med. Chem., 31, 517-526 .
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 5.1.1.1 | drug development | Alr is a target for the development of antibacterial drugs | Geobacillus stearothermophilus |
| 5.1.1.1 | drug development | Alr is a target for the development of antibacterial drugs | Chlamydia pneumoniae |
| 5.1.1.1 | drug development | Alr is a target for the development of antibacterial drugs | Escherichia coli |
| 5.1.1.1 | drug development | Alr is a target for the development of antibacterial drugs | Pseudomonas aeruginosa |
Crystallization (Commentary)
| EC Number | Crystallization (Comment) | Organism |
|---|---|---|
| 5.1.1.1 | enzyme in complex with pyridoxyl 5'-phosphate and inhibitor acetate, PDB ID 1SFT | Geobacillus stearothermophilus |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.1.1.1 | ((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 | - |
Pseudomonas aeruginosa |  |
| 5.1.1.1 | (1-aminoethyl)boronic acid | - |
Bacillus cereus | |
| 5.1.1.1 | (1-aminoethyl)boronic acid | Ala-B | Geobacillus stearothermophilus | |
| 5.1.1.1 | (2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate | - |
Enterobacter sp. | |
| 5.1.1.1 | (2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | (2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | (2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | (2S)-1-oxo-1-([(1R)-1-phosphonoethyl]amino)propan-2-yl L-methioninate | - |
Serratia marcescens | |
| 5.1.1.1 | (2S)-1-oxo-1-[[(1R)-1-phosphonoethyl]amino]propan-2-yl L-methioninate | - |
Enterococcus faecalis | |
| 5.1.1.1 | (2S)-1-oxo-1-[[(1R)-1-phosphonoethyl]amino]propan-2-yl L-methioninate | - |
Staphylococcus aureus | |
| 5.1.1.1 | (6R)-3-[(D-alanyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | - |
Bacillus cereus | |
| 5.1.1.1 | (6R)-3-[(D-alanyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | - |
Enterococcus faecalis | |
| 5.1.1.1 | (6R)-3-[(D-alanyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | (6R)-3-[(D-alanyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | - |
Listeria monocytogenes | |
| 5.1.1.1 | 1,2,4-thiadiazolidine-3,5-dione | - |
Staphylococcus aureus | |
| 5.1.1.1 | 2-(2-chloro-4-nitrophenyl)-4-(2,3-dihydro-1H-inden-2-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 2-(2-chloro-4-nitrophenyl)-4-(2,3-dihydro-1H-inden-2-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 2-(2-chloro-4-nitrophenyl)-4-(cyclopropylmethyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 2-(2-chloro-4-nitrophenyl)-4-(cyclopropylmethyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 2-(2-chloro-6-methylphenyl)-4-(cyclopropylmethyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 2-(2-chloro-6-methylphenyl)-4-(cyclopropylmethyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 2-(3,5-dimethyl-1,2-oxazol-4-yl)-4-(4-fluorophenyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 2-(3,5-dimethyl-1,2-oxazol-4-yl)-4-(4-fluorophenyl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 2-(3-chloro-4-fluorophenyl)-4-(2,3-dihydro-1H-inden-2-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 2-(3-chloro-4-fluorophenyl)-4-(2,3-dihydro-1H-inden-2-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 3-halovinylglycine | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | 4-(2,3-dihydro-1H-inden-2-yl)-2-[(3-ethylphenyl)methyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-(2,3-dihydro-1H-inden-2-yl)-2-[(3-ethylphenyl)methyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 4-(cyclopropylmethyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-(cyclopropylmethyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 4-(cyclopropylmethyl)-2-[2-(trifluoromethyl)phenyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-(cyclopropylmethyl)-2-[2-(trifluoromethyl)phenyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 4-methyl-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-methyl-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 4-methyl-2-phenyl-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-methyl-2-phenyl-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | 4-[4-(propan-2-yl)phenyl]-2-[4-[(trifluoromethyl)sulfanyl]phenyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | 4-[4-(propan-2-yl)phenyl]-2-[4-[(trifluoromethyl)sulfanyl]phenyl]-1,2,4-thiadiazolidine-3,5-dione | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | acetate | enzyme-inhibitor complex structure, with pyridoxyl 5'-phosphate, PDB ID 1SFT | Geobacillus stearothermophilus | |
| 5.1.1.1 | alafosfalin | - |
Bacillus cereus | |
| 5.1.1.1 | alafosfalin | - |
Enterobacter sp. | |
| 5.1.1.1 | alafosfalin | - |
Enterococcus faecalis | |
| 5.1.1.1 | alafosfalin | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | alafosfalin | - |
Escherichia coli | |
| 5.1.1.1 | alafosfalin | - |
Geobacillus stearothermophilus | |
| 5.1.1.1 | alafosfalin | - |
Lactiplantibacillus plantarum | |
| 5.1.1.1 | alafosfalin | - |
Lactococcus lactis | |
| 5.1.1.1 | alafosfalin | - |
Listeria monocytogenes | |
| 5.1.1.1 | alafosfalin | - |
Methanococcus maripaludis | |
| 5.1.1.1 | alafosfalin | effective in reducing D-alanine pool levels, alafosfalin forms an external aldimine with the bound PLP cofactor, but is neither racemised nor efficiently hydrolyzed and upon formation of the external aldimine, the phosphonate group interacts with putative catalytic residues and thereby renders them unavailable for catalysis | Mycobacterium tuberculosis | |
| 5.1.1.1 | alafosfalin | - |
Proteus mirabilis | |
| 5.1.1.1 | alafosfalin | selective inhibitor of peptidoglycan biosynthesis in both Grampositive and Gram-negative bacteria | Pseudomonas aeruginosa | |
| 5.1.1.1 | alafosfalin | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | alafosfalin | - |
Serratia marcescens | |
| 5.1.1.1 | alafosfalin | effective in reducing D-alanine pool levels, alafosfalin forms an external aldimine with the bound PLP cofactor, but is neither racemised nor efficiently hydrolyzed and upon formation of the external aldimine, the phosphonate group interacted with putative catalytic residues and thereby renders them unavailable for catalysis | Staphylococcus aureus | |
| 5.1.1.1 | beta-Chloro-D-alanine | 90-95% inhibition | Escherichia coli | |
| 5.1.1.1 | beta-Chloro-D-alanine | 90-95% inhibition | Pseudomonas aeruginosa | |
| 5.1.1.1 | beta-Chloro-D-alanine | effective in the inhibition of bacterial growth | Staphylococcus aureus | |
| 5.1.1.1 | beta-chloro-L-alanine | - |
Escherichia coli | |
| 5.1.1.1 | beta-chloro-L-alanine | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | beta-chloro-L-alanine | effective in the inhibition of bacterial growth like that of the D-isomer. But the L-isomer has less specificity towards the concerned Alr enzymes due to its inhibitory activity towards decarboxylase and transaminases. This results in the blockage of the production of essential L-amino acids with a loss of viability of bacterial and mammalial cells | Staphylococcus aureus | |
| 5.1.1.1 | beta-chloroalanine | enantiomers of beta-chloroalanine as Alr inhibitors | Geobacillus stearothermophilus | |
| 5.1.1.1 | chlorovinyl glycine | - |
Enterococcus faecalis | |
| 5.1.1.1 | chlorovinyl glycine | - |
Escherichia coli | |
| 5.1.1.1 | chlorovinyl glycine | - |
Geobacillus stearothermophilus | |
| 5.1.1.1 | chlorovinyl glycine | - |
Lactiplantibacillus plantarum | |
| 5.1.1.1 | chlorovinyl glycine | - |
Lactococcus lactis | |
| 5.1.1.1 | chlorovinyl glycine | - |
Methanococcus maripaludis | |
| 5.1.1.1 | chlorovinylglycine | - |
Bacillus cereus | |
| 5.1.1.1 | chlorovinylglycine | - |
Enterobacter sp. | |
| 5.1.1.1 | chlorovinylglycine | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | chlorovinylglycine | - |
Listeria monocytogenes | |
| 5.1.1.1 | chlorovinylglycine | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | chlorovinylglycine | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | chlorovinylglycine | - |
Proteus mirabilis | |
| 5.1.1.1 | chlorovinylglycine | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | chlorovinylglycine | - |
Serratia marcescens | |
| 5.1.1.1 | chlorovinylglycine | - |
Staphylococcus aureus | |
| 5.1.1.1 | D-cycloserine | - |
Bacillus cereus | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Chlamydia pneumoniae | |
| 5.1.1.1 | D-cycloserine | - |
Enterobacter sp. | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Enterococcus faecalis | |
| 5.1.1.1 | D-cycloserine | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | D-cycloserine | competitive inhibition, importance of N2-structural site in cyloserine for bioactivity | Escherichia coli | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Geobacillus stearothermophilus | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Lactiplantibacillus plantarum | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Lactococcus lactis | |
| 5.1.1.1 | D-cycloserine | - |
Listeria monocytogenes | |
| 5.1.1.1 | D-cycloserine | importance of N2-structural site in cyloserine for bioactivity | Methanococcus maripaludis | |
| 5.1.1.1 | D-cycloserine | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | D-cycloserine | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | D-cycloserine | - |
Proteus mirabilis | |
| 5.1.1.1 | D-cycloserine | competitive inhibition, importance of N2-structural site in cyloserine for bioactivity | Pseudomonas aeruginosa | |
| 5.1.1.1 | D-cycloserine | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | D-cycloserine | - |
Serratia marcescens | |
| 5.1.1.1 | D-cycloserine | competitive inhibitor, importance of N2-structural site in cyloserine for bioactivity | Staphylococcus aureus | |
| 5.1.1.1 | glycine | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | L-Cycloserine | competitive inhibition, importance of N2-structural site in cyloserine for bioactivity | Escherichia coli | |
| 5.1.1.1 | L-Cycloserine | importance of N2-structural site in cyloserine for bioactivity | Geobacillus stearothermophilus | |
| 5.1.1.1 | L-Cycloserine | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | L-Cycloserine | competitive inhibition, importance of N2-structural site in cyloserine for bioactivity | Pseudomonas aeruginosa | |
| 5.1.1.1 | L-Cycloserine | competitive inhibitor, importance of N2-structural site in cyloserine for bioactivity | Staphylococcus aureus | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Enterobacter sp. | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Enterococcus faecalis | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Serratia marcescens | |
| 5.1.1.1 | L-leucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Staphylococcus aureus | |
| 5.1.1.1 | L-norvalyl-L-chlorovinylglycine | - |
Enterococcus faecalis | |
| 5.1.1.1 | L-norvalyl-L-chlorovinylglycine | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | L-norvalyl-L-chlorovinylglycine | - |
Listeria monocytogenes | |
| 5.1.1.1 | L-norvalyl-L-chlorovinylglycine | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | L-norvalyl-L-chlorovinylglycine | - |
Staphylococcus aureus | |
| 5.1.1.1 | additional information | structure-based inhibitor design | Geobacillus stearothermophilus | |
| 5.1.1.1 | additional information | no inhibition by O-carbamoyl-L-serine | Lactiplantibacillus plantarum | |
| 5.1.1.1 | additional information | no inhibition by O-carbamoyl-L-serine | Lactococcus lactis | |
| 5.1.1.1 | additional information | N2-substitution of carboxybenzyl-protected derivatives of D,L-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 N2 position exhibits modest inhibitory activity against purified Alr enzyme from Mycobacterium tuberculosis, Ki = 0.36 mM | Mycobacterium tuberculosis | |
| 5.1.1.1 | 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 | Pseudomonas aeruginosa | |
| 5.1.1.1 | additional information | no inhibition by O-carbamoyl-L-serine. N2-substitution of carboxybenzyl-protected derivatives of D,L-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 Streptococcus aureus, Ki = 1.16 mM | Staphylococcus aureus | |
| 5.1.1.1 | N2-(2-aminodecanoyl)-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Proteus mirabilis | |
| 5.1.1.1 | N2-(2-aminodecanoyl)-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | N2-(2-aminodecanoyl)-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Staphylococcus aureus | |
| 5.1.1.1 | norleucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | moderate in vivo activity | Escherichia coli | |
| 5.1.1.1 | norleucyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Staphylococcus aureus | |
| 5.1.1.1 | norvalyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | moderate in vivo activity | Escherichia coli | |
| 5.1.1.1 | norvalyl-N-[(1R)-1-phosphonoethyl]-L-alaninamide | - |
Staphylococcus aureus | |
| 5.1.1.1 | O-acetyl-D-serine | reversible inhibitor | Staphylococcus aureus | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Bacillus cereus | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Enterobacter sp. | |
| 5.1.1.1 | O-carbamoyl-D-serine | good inhibitor, determination of primary site of action is based on the observed accumulation of UDP-MurNAc-L-Ala-D-Glu-L-Lys and on the absence of D-Ala-O-carbamyl-D-serine accumulation | Enterococcus faecalis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Escherichia coli | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Geobacillus stearothermophilus | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Lactiplantibacillus plantarum | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Lactococcus lactis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Listeria monocytogenes | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Methanococcus maripaludis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Mycobacterium tuberculosis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Mycolicibacterium smegmatis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Proteus mirabilis | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Pseudomonas aeruginosa | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Serratia marcescens | |
| 5.1.1.1 | O-carbamoyl-D-serine | - |
Staphylococcus aureus | |
| 5.1.1.1 | [(1R)-1-amino-2-chloroethyl]phosphonic acid | - |
Pseudomonas aeruginosa | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.1.1.1 | additional information | - |
additional information | Michaelis-Menten kinetics | Staphylococcus aureus | |
| 5.1.1.1 | 0.46 | - |
D-alanine | pH and temperature not specified in the publication | Staphylococcus aureus | |
| 5.1.1.1 | 0.48 | - |
D-alanine | pH and temperature not specified in the publication | Enterococcus faecalis | |
| 5.1.1.1 | 0.97 | - |
L-alanine | pH and temperature not specified in the publication | Staphylococcus aureus | |
| 5.1.1.1 | 6.8 | - |
L-alanine | pH and temperature not specified in the publication | Enterococcus faecalis | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.1.1.1 | L-alanine | Salmonella enterica subsp. enterica serovar Typhimurium | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Lactiplantibacillus plantarum | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Staphylococcus aureus | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Mycolicibacterium smegmatis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Geobacillus stearothermophilus | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Lactococcus lactis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Serratia marcescens | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Enterococcus faecalis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Bacillus cereus | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Proteus mirabilis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Mycobacterium tuberculosis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Enterobacter sp. | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Methanococcus maripaludis | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Listeria monocytogenes | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Erysipelothrix rhusiopathiae | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Escherichia coli | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Pseudomonas aeruginosa | - |
D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | - |
D-alanine | - |
r | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 5.1.1.1 | Bacillus cereus | - |
- |
- |
| 5.1.1.1 | Chlamydia pneumoniae | - |
- |
- |
| 5.1.1.1 | Enterobacter sp. | - |
- |
- |
| 5.1.1.1 | Enterococcus faecalis | - |
- |
- |
| 5.1.1.1 | Erysipelothrix rhusiopathiae | - |
- |
- |
| 5.1.1.1 | Escherichia coli | P0A6B4 | - |
- |
| 5.1.1.1 | Geobacillus stearothermophilus | - |
- |
- |
| 5.1.1.1 | Lactiplantibacillus plantarum | - |
- |
- |
| 5.1.1.1 | Lactococcus lactis | - |
- |
- |
| 5.1.1.1 | Listeria monocytogenes | - |
- |
- |
| 5.1.1.1 | Methanococcus maripaludis | - |
- |
- |
| 5.1.1.1 | Mycobacterium tuberculosis | - |
- |
- |
| 5.1.1.1 | Mycolicibacterium smegmatis | - |
- |
- |
| 5.1.1.1 | no activity in Homo sapiens | - |
- |
- |
| 5.1.1.1 | Proteus mirabilis | - |
- |
- |
| 5.1.1.1 | Pseudomonas aeruginosa | Q9HUN4 | - |
- |
| 5.1.1.1 | Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | Q9HUN4 | - |
- |
| 5.1.1.1 | Salmonella enterica subsp. enterica serovar Typhimurium | - |
- |
- |
| 5.1.1.1 | Serratia marcescens | - |
- |
- |
| 5.1.1.1 | Staphylococcus aureus | - |
- |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.1.1.1 | L-alanine | - |
Salmonella enterica subsp. enterica serovar Typhimurium | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Lactiplantibacillus plantarum | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Staphylococcus aureus | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Mycolicibacterium smegmatis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Geobacillus stearothermophilus | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Lactococcus lactis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Serratia marcescens | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Enterococcus faecalis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Bacillus cereus | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Proteus mirabilis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Mycobacterium tuberculosis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Enterobacter sp. | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Methanococcus maripaludis | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Listeria monocytogenes | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Chlamydia pneumoniae | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Erysipelothrix rhusiopathiae | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Escherichia coli | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Pseudomonas aeruginosa | D-alanine | - |
r | |
| 5.1.1.1 | L-alanine | - |
Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | D-alanine | - |
r | |
| 5.1.1.1 | additional information | purified chlamydial GlyA also exhibits racemase activity on L-Ala in vitro | Chlamydia pneumoniae | ? | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 5.1.1.1 | homodimer | the homodimeric enzyme of 388 residues formed by a head-to-tail association of two monomers. Each monomer is composed of two folded domains: (i) an N-terminal domain formed by the portion 1-240 and (ii) a C-terminal domain with the remaining portion of the monomer (241-388). The N-terminal domain consists of an eight-stranded alpha/beta-barrel, while the C-terminal domain is made up of beta-strands. Molecular dynamics study | Geobacillus stearothermophilus |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 5.1.1.1 | ALR | - |
Salmonella enterica subsp. enterica serovar Typhimurium |
| 5.1.1.1 | ALR | - |
Lactiplantibacillus plantarum |
| 5.1.1.1 | ALR | - |
Staphylococcus aureus |
| 5.1.1.1 | ALR | - |
Mycolicibacterium smegmatis |
| 5.1.1.1 | ALR | - |
Geobacillus stearothermophilus |
| 5.1.1.1 | ALR | - |
Lactococcus lactis |
| 5.1.1.1 | ALR | - |
Serratia marcescens |
| 5.1.1.1 | ALR | - |
Enterococcus faecalis |
| 5.1.1.1 | ALR | - |
Bacillus cereus |
| 5.1.1.1 | ALR | - |
Proteus mirabilis |
| 5.1.1.1 | ALR | - |
Mycobacterium tuberculosis |
| 5.1.1.1 | ALR | - |
Enterobacter sp. |
| 5.1.1.1 | ALR | - |
Methanococcus maripaludis |
| 5.1.1.1 | ALR | - |
Listeria monocytogenes |
| 5.1.1.1 | ALR | - |
Chlamydia pneumoniae |
| 5.1.1.1 | ALR | - |
Erysipelothrix rhusiopathiae |
| 5.1.1.1 | ALR | - |
Escherichia coli |
| 5.1.1.1 | ALR | - |
Pseudomonas aeruginosa |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Salmonella enterica subsp. enterica serovar Typhimurium | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Lactiplantibacillus plantarum | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Staphylococcus aureus | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Mycolicibacterium smegmatis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Lactococcus lactis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Serratia marcescens | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Enterococcus faecalis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Bacillus cereus | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Proteus mirabilis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Mycobacterium tuberculosis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Enterobacter sp. | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Methanococcus maripaludis | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Listeria monocytogenes | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Chlamydia pneumoniae | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Erysipelothrix rhusiopathiae | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Escherichia coli | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on | Pseudomonas aeruginosa | |
| 5.1.1.1 | pyridoxal 5'-phosphate | PLP, dependent on, enzyme-cofactor complex structure, with inhibitor acetate, PDB ID 1SFT | Geobacillus stearothermophilus | |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.1.1.1 | 0.0086 | - |
D-cycloserine | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
| 5.1.1.1 | 0.0086 | - |
L-Cycloserine | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
| 5.1.1.1 | 0.0138 | - |
D-cycloserine | pH and temperature not specified in the publication | Pseudomonas aeruginosa | |
| 5.1.1.1 | 0.0138 | - |
L-Cycloserine | pH and temperature not specified in the publication | Pseudomonas aeruginosa | |
| 5.1.1.1 | 0.073 | - |
D-cycloserine | pH and temperature not specified in the publication | Staphylococcus aureus | |
| 5.1.1.1 | 0.073 | - |
L-Cycloserine | pH and temperature not specified in the publication | Staphylococcus aureus | |
| 5.1.1.1 | 0.4 | - |
alafosfalin | pH and temperature not specified in the publication | Staphylococcus aureus | |
| 5.1.1.1 | 9 | - |
alafosfalin | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 5.1.1.1 | 0.65 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | D-cycloserine | |
| 5.1.1.1 | 2.1 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | L-Cycloserine | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Salmonella enterica subsp. enterica serovar Typhimurium |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Lactiplantibacillus plantarum |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Staphylococcus aureus |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Mycolicibacterium smegmatis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Lactococcus lactis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Serratia marcescens |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Enterococcus faecalis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Bacillus cereus |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Proteus mirabilis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Mycobacterium tuberculosis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Enterobacter sp. |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Listeria monocytogenes |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Erysipelothrix rhusiopathiae |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme | Escherichia coli |
| 5.1.1.1 | 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 | Pseudomonas aeruginosa |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal 5'-phosphate-dependent amino acid racemase enzyme. The genome sequences of methanogenic archaeon, Methanococcus maripaludis reveals the presence of alanine dehydrogenase gene adjacent to genes for alanine racemase and alanine permease, apparently acquired from bacteria | Methanococcus maripaludis |
| 5.1.1.1 | evolution | alanine racemase is a fold type III pyridoxal-5'-phosphate-dependent amino acid racemase enzyme | Geobacillus stearothermophilus |
| 5.1.1.1 | malfunction | growth of the Alr mutant on a mixture of D- and L-alanine is compromised | Methanococcus maripaludis |
| 5.1.1.1 | 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 | Pseudomonas aeruginosa |
| 5.1.1.1 | 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 | Geobacillus stearothermophilus |
| 5.1.1.1 | 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 | Escherichia coli |
| 5.1.1.1 | 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 | Pseudomonas aeruginosa |
| 5.1.1.1 | physiological function | in addition to its function in the utilisation of D-alanine, Alr exhibits a role in protecting the system from inhibition by D-alanine | Methanococcus maripaludis |
| 5.1.1.1 | physiological function | in the absence of genes coding for alanine racemase Alr and DadX homologues in Chlamydia pneumonia a serine hydroxymethyl transferase GlyA serves as a source of D-Ala. 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 | Chlamydia pneumoniae |
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