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Literature summary extracted from

  • Walker, S.; Cumming, H.; Parker, E.
    Substrate and reaction intermediate mimics as inhibitors of 3-deoxy-d-arabino-heptulosonate 7-phosphate synthase (2009), Org. Biomol. Chem., 7, 3031-3035.
No PubMed abstract available

Activating Compound

EC Number Activating Compound Comment Organism Structure
2.5.1.54 additional information enzyme uses divalent metal ion to activate a phosphorylated carbohydrate-like substrate Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.54 (2R)-2-(phosphonooxy)propanoic acid mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate Escherichia coli
2.5.1.54 (2S)-2-(phosphonooxy)propanoic acid mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate Escherichia coli
2.5.1.54 (2Z)-3-phosphono-2-(trifluoromethyl)prop-2-enoic acid trifluorinated phosphonate Escherichia coli
2.5.1.54 (E)-2-methyl-3-phosphonoacrylic acid most potent of the tested inhibitors mimicking intermediates in the reaction, vinyl phosphonate 4 Escherichia coli
2.5.1.54 2-(phosphonomethyl)prop-2-enoic acid mimics substrate phosphoenolpyruvate, and should be inert due to alkene structure but lacking an electron-donor, acts as competitive inhibitor Escherichia coli
2.5.1.54 fosmidomycin uncompetitive inhibitor, maximum level of inhibition after 10 min incubation, extent of inhibition dependent on the type of the metal cofactor, competitive inhibitor with respect to phosphoenolpyruvate Escherichia coli
2.5.1.54 additional information structure and reaction intermediate mimic inhibitors; sulfoenolpyruvate 7 mimics substrate phosphoenolpyruvate, sulfate exchanges phosphate ester, no inhibition up to a concentration of 10 mM Escherichia coli

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.5.1.54 Co2+ 2fold lower inhibition by fosmidomycin with Co2+ as cofactor than with Mn2+ or Fe2+, no effect with sulfoenolpyruvate 7 as potential inhibitor Escherichia coli
2.5.1.54 Fe2+ 2fold greater inhibition by fosmidomycin with Fe2+ as cofactor than with Co2+, no effect with sulfoenolpyruvate 7 as potential inhibitor Escherichia coli
2.5.1.54 Mn2+ 2fold greater inhibition by fosmidomycin with Mn2+ as cofactor than with Co2+, no effect with sulfoenolpyruvate 7 as potential inhibitor Escherichia coli
2.5.1.54 Zn2+ no effect with sulfoenolpyruvate 7 as potential inhibitor Escherichia coli

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.54 phosphoenolpyruvate + D-erythrose 4-phosphate + H2O Escherichia coli
-
 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.54 Escherichia coli
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.54 phosphoenolpyruvate + D-erythrose 4-phosphate + H2O
-
 Escherichia coli 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.54 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase
-
 Escherichia coli
2.5.1.54 DAH7P
-
 Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.5.1.54 0.0047
-
 (E)-2-methyl-3-phosphonoacrylic acid buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli
2.5.1.54 0.0088
-
 (2Z)-3-phosphono-2-(trifluoromethyl)prop-2-enoic acid buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli
2.5.1.54 0.035
-
 fosmidomycin buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli
2.5.1.54 0.049
-
 (2R)-2-(phosphonooxy)propanoic acid buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli
2.5.1.54 0.27
-
 2-(phosphonomethyl)prop-2-enoic acid buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli
2.5.1.54 0.67
-
 (2S)-2-(phosphonooxy)propanoic acid buffer bis-tris-propane, 50 mM, pH 6.8, Mn2+, UV-visible spectroscopy at 232 nm, substrates phosphoenolpyruvate and D-erythrose 4-phosphate Escherichia coli

General Information

EC Number General Information Comment Organism
2.5.1.54 metabolism catalysis of first step of shipmate pathway to aromatic amino acids Escherichia coli