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Literature summary extracted from

  • Cushman, M.; Jin, G.; Sambaiah, T.; Illarionov, B.; Fischer, M.; Ladenstein, R.; Bacher, A.
    Design, synthesis, and biochemical evaluation of 1,5,6,7-tetrahydro-6,7-dioxo-9-D-ribitylaminolumazines bearing alkyl phosphate substituents as inhibitors of lumazine synthase and riboflavin synthase (2005), J. Org. Chem., 70, 8162-8170.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.78 1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
-
 Bacillus subtilis
2.5.1.78 1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol
-
 Mycobacterium tuberculosis
2.5.1.78 1-deoxy-1-[2,4,6,7-tetraoxo-5-[4-(phosphonooxy)butyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
-
 Mycobacterium tuberculosis
2.5.1.78 1-deoxy-1-[2,4,6,7-tetraoxo-5-[5-(phosphonooxy)pentyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol
-
 Mycobacterium tuberculosis
2.5.1.78 1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
 Bacillus subtilis
2.5.1.78 1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
 Mycobacterium tuberculosis
2.5.1.78 1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
 Bacillus subtilis
2.5.1.78 1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
 Mycobacterium tuberculosis
2.5.1.78 4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
-
 Bacillus subtilis
2.5.1.78 4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate
-
 Mycobacterium tuberculosis
2.5.1.78 5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
-
 Bacillus subtilis
2.5.1.78 5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate Bacillus subtilis penultimate step of riboflavin biosynthesis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate Mycobacterium tuberculosis penultimate step of riboflavin biosynthesis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.78 Bacillus subtilis
-
-
-
2.5.1.78 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
-
 Bacillus subtilis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
-
 Mycobacterium tuberculosis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate penultimate step of riboflavin biosynthesis Bacillus subtilis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?
2.5.1.78 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione + (S)-2-hydroxy-3-oxobutyl dihydrogen phosphate penultimate step of riboflavin biosynthesis Mycobacterium tuberculosis 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + 2 H2O
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.78 37
-
 assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.5.1.78 7
-
 assay at Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.5.1.78 0.0000041
-
 1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.0000047
-
 1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.000012
-
 5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.000012
-
 1-deoxy-1-[2,4,6,7-tetraoxo-5-[5-(phosphonooxy)pentyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.000036
-
 4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.000036
-
 1-deoxy-1-[2,4,6,7-tetraoxo-5-[4-(phosphonooxy)butyl]-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl]-D-ribitol pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.0014
-
 1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol pH 7.0, 37°C Mycobacterium tuberculosis
2.5.1.78 0.0078
-
 1-deoxy-1-(2,4,6,7-tetraoxo-1,3,4,5,6,7-hexahydropteridin-8(2H)-yl)-D-ribitol pH 7.0, 37°C Bacillus subtilis
2.5.1.78 0.027
-
 5-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)pentane 1-phosphate pH 7.0, 37°C Bacillus subtilis
2.5.1.78 0.15
-
 4-(1,5,6,7-tetrahydro-6,7-dioxo-8-D-ribityllumazin-5-yl)butane 1-phosphate pH 7.0, 37°C Bacillus subtilis
2.5.1.78 0.17
-
 1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol pH 7.0, 37°C Bacillus subtilis
2.5.1.78 0.27
-
 1-deoxy-1-[2,6,8-trioxo-7-[5-(phosphonooxy)pentyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol pH 7.0, 37°C Bacillus subtilis