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Literature summary extracted from

  • Perruchon, J.; Ortmann, R.; Altenkaemper, M.; Silber, K.; Wiesner, J.; Jomaa, H.; Klebe, G.; Schlitzer, M.
    Studies addressing the importance of charge in the binding of fosmidomycin-like molecules to deoxyxylulosephosphate reductoisomerase (2008), ChemMedChem, 3, 1232-1241.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.267 fosmidomycin
-
 Escherichia coli
1.1.1.267 FR900098 fosmidomycin homologue Escherichia coli
1.1.1.267 additional information neither the sulfone (N-hydroxy-N-[3-(alkylsulfonyl)propyl]acetamides) nor the sulfonamide derivatives (N-hydroxy-N-(3-sulfamoylpropyl) acetamide and N-hydroxy-N-(3-(N-alkylsulfamoyl)propyl)acetamide) of FR900098 display any significant inhibitory activity against DXR at a concentration of 0.03 mM. Importance of the negative charge for the binding of fosmidomycin-like inhibitors to DXR. Uncharged molecules are virtually inactive whereas derivatives that possess only one instead of two negative charges are markedly less active. It is possible to regain some of the activity that is lost by the reduction of the charge by occupation of hitherto unexploited areas of the enzyme Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
-
 Escherichia coli
1.1.1.267 [3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
-
 Escherichia coli

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.1.1.267 Mg2+
-
 Escherichia coli
1.1.1.267 Mn2+
-
 Escherichia coli

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.267 Escherichia coli P45568
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.267 1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
 Escherichia coli 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.267 deoxyxylulosephosphate reductoisomerase
-
 Escherichia coli
1.1.1.267 DOXP reductoisomerase
-
 Escherichia coli
1.1.1.267 DXR
-
 Escherichia coli

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.267 NADPH
-
 Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.267 0.000035
-
 at 0.03 mM Escherichia coli fosmidomycin
1.1.1.267 0.000035
-
 at 0.03 mM Escherichia coli FR900098
1.1.1.267 0.00049
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
1.1.1.267 0.0016
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
1.1.1.267 0.0021
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
1.1.1.267 0.0024
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
1.1.1.267 0.0039
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
1.1.1.267 0.016
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
1.1.1.267 0.023
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
1.1.1.267 0.05
-
 at 0.03 mM Escherichia coli [3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester