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Literature summary for 1.11.1.23 extracted from

  • Yan, F.; Munos, J.W.; Liu, P.; Liu, H.W.
    Biosynthesis of fosfomycin, re-examination and re-confirmation of a unique Fe(II)- and NAD(P)H-dependent epoxidation reaction (2006), Biochemistry, 45, 11473-11481.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.11.1.23

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ Fe2+ is the only metal ion that is effective to reconstitute HppE activity. Zn2+ cannot replace Fe2+ in the HppE reaction Streptomyces wedmorensis

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Streptomyces wedmorensis Q56185
-
-

Reaction

Reaction Comment Organism Reaction ID
(S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O an iron-redox mechanism is proposed in which the active site bound Fe2+ serves as a Lewis acid to activate the 2-OH group of (S)-2-hydroxypropylphosphonic acid, and the epoxide ring is formed by the attack of the 2-OH group at C-1 coupled with the transfer of the C-1 hydrogen as a hydride ion to the bound FMN Streptomyces wedmorensis
a

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
HppE
-
 Streptomyces wedmorensis

Cofactor

Cofactor Comment Organism Structure
FMN FMN is an artificial electron mediator for the in vitro HppE activity. It accepts a hydride from NADH and then passes electrons on to reduce the iron center of HppE. Several non-flavin electron mediators can replace FMN Streptomyces wedmorensis
NADH
-
 Streptomyces wedmorensis