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Literature summary extracted from

  • Cushman, M.; Yang, D.; Gerhardt, S.; Huber, R.; Fischer, M.; Kis, K.; Bacher, A.
    Design, synthesis, and evaluation of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase (2002), J. Org. Chem., 67, 5807-5816.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.9 expression of beta60 capsid Escherichia coli
2.5.1.78 expression of beta60 capsid Bacillus subtilis

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.5.1.9 molecular modeling of inhibitors to the active site Escherichia coli
2.5.1.78 molecular modeling of inhibitors to the active site Bacillus subtilis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.9 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate competitive, comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione competitive, comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.9 9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione competitive, comparison with inhibition of Bacillus subtilis lumazine synthase Escherichia coli
2.5.1.78 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid uncompetitive, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate competitive, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate uncompetitive, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione mixed inhibition, comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis
2.5.1.78 9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione comparison with inhibition of Escherichia coli riboflavin synthase Bacillus subtilis

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.9 Escherichia coli
-
-
-
2.5.1.78 Bacillus subtilis
-
 lumazine synthase/riboflavin synthase complex
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.9 6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
-
 Escherichia coli riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
 ?
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
-
 ?

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.5.1.9 0.00061
-
 9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione pH 7.5, 37°C Escherichia coli
2.5.1.9 0.02
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid pH 7.5, 37°C Escherichia coli
2.5.1.9 0.15
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate pH 7.5, 37°C Escherichia coli
2.5.1.9 0.65
-
 6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C Escherichia coli
2.5.1.9 1
-
 5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C Escherichia coli
2.5.1.9 1
-
 5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C Escherichia coli
2.5.1.9 1.6
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate pH 7.5, 37°C Escherichia coli
2.5.1.78 0.046
-
 9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.084
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.094
-
 6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.12
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.13
-
 5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.16
-
 4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis
2.5.1.78 0.18
-
 5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione pH 7.5, 37°C, recombinant beta60 capsid Bacillus subtilis