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Literature summary extracted from

  • Anthony, K.G.; Strych, U.; Yeung, K.R.; Shoen, C.S.; Perez, O.; Krause, K.L.; Cynamon, M.H.; Aristoff, P.A.; Koski, R.A.
    New classes of alanine racemase inhibitors identified by high-throughput screening show antimicrobial activity against Mycobacterium tuberculosis (2011), PLoS ONE, 6, e20374.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
5.1.1.1 expressed in Escherichia coli as an N-terminal polyhistidine fusion Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
5.1.1.1 (4R)-4-amino-3-isoxazolidinone
-
Mycobacterium tuberculosis
5.1.1.1 1,1'-(2-oxido-1,2,5-oxadiazole-3,4-diyl)-bis (1-(2-thienyl))-methanone
-
Mycobacterium tuberculosis
5.1.1.1 1-amino-cyclopropane phosphonate
-
Mycobacterium tuberculosis
5.1.1.1 2-(2-hydroxyphenoxy)-N-methylacetamide
-
Mycobacterium tuberculosis
5.1.1.1 2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)-N-[2-(4-ethoxyphenyl)ethyl]acetamide
-
Mycobacterium tuberculosis
5.1.1.1 2-(4-methoxyphenyl)-1-morpholin-4-ylethanethione
-
Mycobacterium tuberculosis
5.1.1.1 2-(4-methylphenyl)-1-morpholin-4-ylethanethione
-
Mycobacterium tuberculosis
5.1.1.1 2-(hydoxyimino)-6-methyl-2H-benzopyran-3-carboxamide
-
Mycobacterium tuberculosis
5.1.1.1 2-(pyridin-3-ylcarbamothioyl sulfanyl)acetic acid
-
Mycobacterium tuberculosis
5.1.1.1 2-N',2-N',7-N',7-N'-tetramethyl-9H-fluorene-2,7-disulfonohydrazide
-
Mycobacterium tuberculosis
5.1.1.1 2-phenyl-1-piperidin-1-ylethanethione
-
Mycobacterium tuberculosis
5.1.1.1 3,3-dihydroxy-1H-quinoline-2,4-dione
-
Mycobacterium tuberculosis
5.1.1.1 5-chloro-N-(3-chloro-4-methoxyphenyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide
-
Mycobacterium tuberculosis
5.1.1.1 6-O-[3-chloro-4-(6-methoxycarbonylpyridine-2-carbonyl)oxyphenyl] 2-O-methyl pyridine-2,6-dicarboxylate
-
Mycobacterium tuberculosis
5.1.1.1 alanine
-
Mycobacterium tuberculosis
5.1.1.1 alanine phosphonate
-
Mycobacterium tuberculosis
5.1.1.1 beta,beta,beta-trifluoroalanine
-
Mycobacterium tuberculosis
5.1.1.1 beta-chloroalanine
-
Mycobacterium tuberculosis
5.1.1.1 beta-fluoroalanine
-
Mycobacterium tuberculosis
5.1.1.1 chloro-vinyl glycine
-
Mycobacterium tuberculosis
5.1.1.1 D-cycloserine
-
Mycobacterium tuberculosis
5.1.1.1 ethyl 3-(pyridin-2-ylthio)propanoate
-
Mycobacterium tuberculosis
5.1.1.1 fluoro-alanine
-
Mycobacterium tuberculosis
5.1.1.1 fluoro-vinyl glycine
-
Mycobacterium tuberculosis
5.1.1.1 L-alanine phosphonic acid
-
Mycobacterium tuberculosis
5.1.1.1 N',N',4-trimethylbenzenesulfonohydrazide
-
Mycobacterium tuberculosis
5.1.1.1 N-benzyl-5-chloro-2-methylsulfonylpyrimidine-4-carboxamide
-
Mycobacterium tuberculosis
5.1.1.1 N-hydroxy-2-(2-hydroxyphenoxy)acetamide
-
Mycobacterium tuberculosis
5.1.1.1 O-carbamoyl-D-serine
-
Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
5.1.1.1 Mycobacterium tuberculosis
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
5.1.1.1
-
Mycobacterium tuberculosis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.1.1.1 D-alanine
-
Mycobacterium tuberculosis L-alanine
-
?

Synonyms

EC Number Synonyms Comment Organism
5.1.1.1 ALR
-
Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
5.1.1.1 pyridoxal 5'-phosphate
-
Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
5.1.1.1 0.02
-
3,3-dihydroxy-1H-quinoline-2,4-dione in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.038
-
ethyl 3-(pyridin-2-ylthio)propanoate in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.08
-
2-phenyl-1-piperidin-1-ylethanethione in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.086
-
(4R)-4-amino-3-isoxazolidinone in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.63
-
N-benzyl-5-chloro-2-methylsulfonylpyrimidine-4-carboxamide in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.68
-
6-O-[3-chloro-4-(6-methoxycarbonylpyridine-2-carbonyl)oxyphenyl] 2-O-methyl pyridine-2,6-dicarboxylate in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.76
-
5-chloro-N-(3-chloro-4-methoxyphenyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis
5.1.1.1 0.93
-
2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)-N-[2-(4-ethoxyphenyl)ethyl]acetamide in 100 mM Tris-Tricine, pH 8.5, 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 0.001
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 6-O-[3-chloro-4-(6-methoxycarbonylpyridine-2-carbonyl)oxyphenyl] 2-O-methyl pyridine-2,6-dicarboxylate
5.1.1.1 0.0016
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-N',2-N',7-N',7-N'-tetramethyl-9H-fluorene-2,7-disulfonohydrazide
5.1.1.1 0.0026
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis ethyl 3-(pyridin-2-ylthio)propanoate
5.1.1.1 0.0028
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(hydoxyimino)-6-methyl-2H-benzopyran-3-carboxamide
5.1.1.1 0.0033
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(4-methoxyphenyl)-1-morpholin-4-ylethanethione
5.1.1.1 0.0049
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 1,1'-(2-oxido-1,2,5-oxadiazole-3,4-diyl)-bis (1-(2-thienyl))-methanone
5.1.1.1 0.0052
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 3,3-dihydroxy-1H-quinoline-2,4-dione
5.1.1.1 0.0057
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(2-hydroxyphenoxy)-N-methylacetamide
5.1.1.1 0.006
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-phenyl-1-piperidin-1-ylethanethione
5.1.1.1 0.0065
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(4-methylphenyl)-1-morpholin-4-ylethanethione
5.1.1.1 0.0068
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis N-benzyl-5-chloro-2-methylsulfonylpyrimidine-4-carboxamide
5.1.1.1 0.0077
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)-N-[2-(4-ethoxyphenyl)ethyl]acetamide
5.1.1.1 0.0082
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 5-chloro-N-(3-chloro-4-methoxyphenyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide
5.1.1.1 0.0082
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis N-hydroxy-2-(2-hydroxyphenoxy)acetamide
5.1.1.1 0.009
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis N',N',4-trimethylbenzenesulfonohydrazide
5.1.1.1 0.0131
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis 2-(pyridin-3-ylcarbamothioyl sulfanyl)acetic acid
5.1.1.1 0.058
-
in 100 mM Tris-Tricine, pH 8.5, temperature not specified in the publication Mycobacterium tuberculosis (4R)-4-amino-3-isoxazolidinone

General Information

EC Number General Information Comment Organism
5.1.1.1 physiological function alanine racemase plays an essential role in cell wall synthesis as it racemizes L-alanine into D-alanine, a key building block in the biosynthesis of peptidoglycan Mycobacterium tuberculosis