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Literature summary extracted from

  • Yan, F.; Moon, S.J.; Liu, P.; Zhao, Z.; Lipscomb, J.D.; Liu, A.; Liu, H.W.
    Determination of the substrate binding mode to the active site iron of (S)-2-hydroxypropylphosphonic acid epoxidase using 17O-enriched substrates and substrate analogues (2007), Biochemistry, 46, 12628-12638.
    View publication on PubMedView publication on EuropePMC

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.11.1.23 Iron O2 binds to the iron, and substrates bind in a single orientation that strongly perturbs the iron environment. Both functional groups of (S)-2-hydroxypropylphosphonic acid bind to Fe(II) ion at the same time as NO, suggesting that the chelated substrate binding mode dominates in solution. The Fe(II)-substrate chelate structure is important to active fosfomycin formation. This fixed orientation may align the substrate next to the iron-bound activated oxygen species thought to mediate hydrogen atom abstraction from the nearest substrate carbon Streptomyces wedmorensis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.11.1.23 (S)-2-hydroxypropylphosphonic acid + 2 NADH + O2 Streptomyces wedmorensis
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 cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?

Organism

EC Number Organism UniProt Comment Textmining
1.11.1.23 Streptomyces wedmorensis Q56185
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.11.1.23 (S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
-
 Streptomyces wedmorensis cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?
1.11.1.23 (S)-2-hydroxypropylphosphonic acid + 2 NADH + O2 bidentate mode of substrate binding to the active site iron in the solution state is established. The binding of the hydroxyl group of the substrates determines the site of oxidation. Use of (R)-2-hydroxypropylphosphonic acid yields the 2-keto-adduct rather than the epoxide Streptomyces wedmorensis cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?

Synonyms

EC Number Synonyms Comment Organism
1.11.1.23 fom4
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 Streptomyces wedmorensis
1.11.1.23 HppE
-
 Streptomyces wedmorensis