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Literature summary for 2.5.1.54 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
Search for more literature for 2.5.1.54

Activating Compound

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

Inhibitors

Inhibitors Comment Organism Structure
(2R)-2-(phosphonooxy)propanoic acid mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate Escherichia coli
(2S)-2-(phosphonooxy)propanoic acid mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate Escherichia coli
(2Z)-3-phosphono-2-(trifluoromethyl)prop-2-enoic acid trifluorinated phosphonate Escherichia coli
(E)-2-methyl-3-phosphonoacrylic acid most potent of the tested inhibitors mimicking intermediates in the reaction, vinyl phosphonate 4 Escherichia coli
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
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
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

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

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

Synonyms

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
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
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
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
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
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

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