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Literature summary for 2.4.2.4 extracted from
- The role of phosphate in the action of thymidine phosphorylase inhibitors: implications for the catalytic mechanism (2010), Bioorg. Med. Chem. Lett., 20, 1648-1651.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil | i.e. AIFU, synthesis, overview, uncompetitive with respect to phosphate, acts as transition state analogs, mimicking the anionic thymine leaving group anchored by their protonated side chains to the enzyme-bound phosphate by electrostatic and H-bonding interactions, modeling of ligand binding at the active site, overview | Escherichia coli |  |
| 5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil | i.e. AIFU, synthesis, overview, uncompetitive with respect to phosphate, acts as transition state analogs, mimicking the anionic thymine leaving group anchored by their protonated side chains to the enzyme-bound phosphate by electrostatic and H-bonding interactions, modeling of ligand binding at the active site, overview | Homo sapiens | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| thymidine + phosphate | Escherichia coli | - |
thymine + 2-deoxy-alpha-D-ribose 1-phosphate | - |
? | |
| thymidine + phosphate | Homo sapiens | - |
thymine + 2-deoxy-alpha-D-ribose 1-phosphate | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Escherichia coli | - |
- |
- |
| Homo sapiens | P19971 | - |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate | SN2-type catalytic mechanism | Escherichia coli | |
| thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate | SN2-type catalytic mechanism | Homo sapiens |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| thymidine + phosphate | - |
Escherichia coli | thymine + 2-deoxy-alpha-D-ribose 1-phosphate | - |
? | |
| thymidine + phosphate | - |
Homo sapiens | thymine + 2-deoxy-alpha-D-ribose 1-phosphate | - |
? | |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | inhibition kinetics, overview | Escherichia coli | |
| additional information | - |
additional information | inhibition kinetics, overview | Homo sapiens | |
| 0.000011 | - |
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil | - |
Escherichia coli | |
| 0.000017 | - |
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil | - |
Homo sapiens | |
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