Literature summary 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.
Metals/Ions
EC Number |
Metals/Ions |
Comment |
Organism |
Structure |
---|
1.11.1.23 |
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)
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 |
- |
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 |
- |
- |
Reaction
EC Number |
Reaction |
Comment |
Organism |
Reaction ID |
---|
1.11.1.23 |
(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 |
|
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 |
? |
|
Synonyms
EC Number |
Synonyms |
Comment |
Organism |
---|
1.11.1.23 |
HppE |
- |
Streptomyces wedmorensis |
Cofactor
EC Number |
Cofactor |
Comment |
Organism |
Structure |
---|
1.11.1.23 |
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 |
|
1.11.1.23 |
NADH |
- |
Streptomyces wedmorensis |
|