Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 2.5.1.78 extracted from

  • Zhang, Y.; Illarionov, B.; Morgunova, E.; Jin, G.; Bacher, A.; Fischer, M.; Ladenstein, R.; Cushman, M.
    A new series of N-[2,4-dioxo-6-d-ribitylamino-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid derivatives as inhibitors of lumazine synthase and riboflavin synthase: design, synthesis, biochemical evaluation, crystallography, and mechanistic implications (2008), J. Org. Chem., 73, 2715-2724.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
in complex with inhibitor N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide and phosphate, to 2.3 A resolution. The aromatic ring of the inhibitor is packed in the hydrophobic environment in the active site formed by Trp27, Ile60, Val81 and Val82, Ile83, Phe90, and Val93 residues of one subunit. The pyrimidine ring is in stacking interaction with the indole ring of Trp27 at a distance of 4 A Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide partial inhibition, inhibition of both lumazine synthase and riboflavin synthase Bacillus subtilis
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide competitive, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9) Mycobacterium tuberculosis
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide competitive, inhibition of both lumazine synthase and riboflavin synthase Schizosaccharomyces pombe
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide partial inhibition, inhibition of both lumazine synthase and riboflavin synthase Bacillus subtilis
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide partial inhibition, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9) Mycobacterium tuberculosis
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide competitive, inhibition of both lumazine synthase and riboflavin synthase Schizosaccharomyces pombe
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester competitive, inhibition of both lumazine synthase and riboflavin synthase Bacillus subtilis
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester partial inhibition, inhibition of both lumazine synthase and riboflavin synthase (EC 2.5.1.9) Mycobacterium tuberculosis
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester mixed type inhibition, inhibition of both lumazine synthase and riboflavin synthase Schizosaccharomyces pombe

Organism

Organism UniProt Comment Textmining
Bacillus subtilis
-
-
-
Mycobacterium tuberculosis
-
-
-
Schizosaccharomyces pombe
-
-
-

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
27
-
assay at Bacillus subtilis
27
-
assay at Schizosaccharomyces pombe
27
-
assay at Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
assay at Bacillus subtilis
7
-
assay at Schizosaccharomyces pombe
7
-
assay at Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00101
-
pH 7.0, 27°C Schizosaccharomyces pombe N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
0.004
-
pH 7.0, 27°C Mycobacterium tuberculosis N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
0.0079
-
pH 7.0, 27°C Schizosaccharomyces pombe N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
0.011
-
pH 7.0, 27°C Schizosaccharomyces pombe N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
0.02
-
pH 7.0, 27°C Bacillus subtilis N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
0.042
-
pH 7.0, 27°C Mycobacterium tuberculosis N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
0.095
-
pH 7.0, 27°C Bacillus subtilis N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
0.11
-
pH 7.0, 27°C Mycobacterium tuberculosis N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
0.607
-
pH 7.0, 27°C Bacillus subtilis N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester