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Literature summary extracted from

  • Munos, J.W.; Moon, S.J.; Mansoorabadi, S.O.; Chang, W.; Hong, L.; Yan, F.; Liu, A.; Liu, H.W.
    Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae (2008), Biochemistry, 47, 8726-8735.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.11.1.23 medicine fosfomycin is a clinically useful antibiotic for the treatment of limb-threatening diabetic foot infections and lower urinary tract infections. It is effective against ciprofloxacin-resistant Escherichia coli, as well as methicillin-resistant and vancomycin-resistant strains of Staphylococcus aureus. The antimicrobial activity of fosfomycin is due to the inactivation of UDP-GlcNAc-3-O-enolpyruvyltransferase, which catalyzes the first committed step in the biosynthesis of peptidoglycan, the main component of the bacterial cell wall Pseudomonas syringae

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.11.1.23 expression in Escherichia coli Pseudomonas syringae

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.11.1.23 EDTA 5 mM, abolishes activity Pseudomonas syringae

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.11.1.23 Iron mononuclear non-heme iron-containing enzyme. Contains about one iron per monomer. Substrate and NO can bind to the ferrous center of the reduced HppE enzyme to form a stable complex Pseudomonas syringae

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.11.1.23 21000
-
 3 * 21000, SDS-PAGE Pseudomonas syringae
1.11.1.23 21315
-
 3 * 21315, calculated from sequence Pseudomonas syringae
1.11.1.23 73000
-
 gel filtration Pseudomonas syringae

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 Pseudomonas syringae
-
 cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?

Organism

EC Number Organism UniProt Comment Textmining
1.11.1.23 Pseudomonas syringae
-
-
-

Posttranslational Modification

EC Number Posttranslational Modification Comment Organism
1.11.1.23 side-chain modification posttranslationally modified by the hydroxylation of Tyr95 Pseudomonas syringae

Purification (Commentary)

EC Number Purification (Comment) Organism
1.11.1.23
-
 Pseudomonas syringae

Reaction

EC Number Reaction Comment Organism Reaction ID
1.11.1.23 (S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O electron transfer is presumed to be the predominant rate-limiting step. Proposed mechanism: the reaction likely begins with hydrogen atom abstraction from the C-1 position by an activated oxygen species. The C-1 centered radical intermediate can then cyclize to form fosfomycin and the reduced iron center Pseudomonas syringae
a

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
-
 Pseudomonas syringae cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?
1.11.1.23 (S)-2-hydroxypropylphosphonic acid + 2 NADH + O2 if either iron, FMN, or NADH is omitted from the reaction mixture, no product formation is detected Pseudomonas syringae cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+ i.e. fosfomycin ?
1.11.1.23 additional information the enzyme also forms 2-oxopropylphosphonic acid from (R)-2-hydroxypropylphosphonic acid, the rate of this reaction is 1.9times faster than the reaction with (S)-2-hydroxypropylphosphonic acid Pseudomonas syringae ?
-
 ?

Subunits

EC Number Subunits Comment Organism
1.11.1.23 trimer 3 * 21000, SDS-PAGE Pseudomonas syringae
1.11.1.23 trimer 3 * 21315, calculated from sequence Pseudomonas syringae

Synonyms

EC Number Synonyms Comment Organism
1.11.1.23 HPP epoxidase
-
 Pseudomonas syringae
1.11.1.23 HppE
-
 Pseudomonas syringae
1.11.1.23 Ps-HppE
-
 Pseudomonas syringae

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.11.1.23 0.0028
-
 (S)-2-hydroxypropylphosphonic acid pH 7.5 Pseudomonas syringae

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.11.1.23 7.5
-
 assay at Pseudomonas syringae

Cofactor

EC Number Cofactor Comment Organism Structure
1.11.1.23 FMN if either iron, FMN, or NADH is omitted from the reaction mixture, no product formation is detected. Due to the fact that the reduction of iron requires single electron transfer and NADH is an obligate two-electron donor, FMN is required to mediate the transfer of reducing equivalents from NADH to the active site iron Pseudomonas syringae
1.11.1.23 NADH NADH is essential for catalysis Pseudomonas syringae