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Literature summary for 4.3.3.7 extracted from

  • Turner, J.J.; Gerrard, J.A.; Hutton, C.A.
    Heterocyclic inhibitors of dihydrodipicolinate synthase are not competitive (2005), Bioorg. Med. Chem., 13, 2133-2140.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(1SR,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium 30 mM, 18% inhibition Escherichia coli
(1SS,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium 9 mM, 48% inhibition Escherichia coli
(2R,6S)-piperidine-2,6-dicarboxylic acid IC50: 20 mM, 83% inhibition at 50 mM Escherichia coli
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid 50 mM, 32% inhibition Escherichia coli
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide 50 mM, 11% inhibition Escherichia coli
(3R,5S)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide 50 mM, 14% inhibition Escherichia coli
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates Escherichia coli
dimethyl (3R,5R)-thiomorpholine-3,5-dicarboxylate 1,1-dioxide 50 mM, 12% inhibition Escherichia coli
dimethyl (3R,5S)-thiomorpholine-3,5-dicarboxylate 50 mM, 36% inhibition Escherichia coli
dimethyl chelidamate IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates Escherichia coli
dimethyl piperidine-2,6-dicarboxylate
-
Escherichia coli
dipicolinic acid IC50: 20 mM, competitive inhibitor Escherichia coli
additional information no inhibition by dipicolinic acid methyl ester, (3R,5S)-thiomorpholine-3,5-dicarboxylic acid compound 20b, (3R,5R)-thiomorpholine-3,5-dicarboxylic acid, compound 23, compound 24b, dimethyl (3R,5S)thiomorpholine-3,5-dicarboxylate 1,1-dioxide Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.14
-
L-aspartate 4-semialdehyde pH 8.0 Escherichia coli
0.38
-
pyruvate pH 8.0 Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-aspartate 4-semialdehyde + pyruvate
-
Escherichia coli dihydrodipicolinate + H2O
-
?

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
6.9
-
dimethyl chelidamate with respect to pyruvate Escherichia coli
14
-
dimethyl chelidamate with respect to L-aspartate 4-semialdehyde Escherichia coli
22
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid with respect to pyruvate Escherichia coli
24.8
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid with respect to L-aspartate 4-semialdehyde Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
14
-
IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates Escherichia coli dimethyl chelidamate
20
-
IC50: 20 mM, 83% inhibition at 50 mM Escherichia coli (2R,6S)-piperidine-2,6-dicarboxylic acid
20
-
IC50: 20 mM, competitive inhibitor Escherichia coli dipicolinic acid
22
-
i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates Escherichia coli 4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid