1.11.1.23: (S)-2-hydroxypropylphosphonic acid epoxidase
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For detailed information about (S)-2-hydroxypropylphosphonic acid epoxidase, go to the full flat file.
Reaction
Synonyms
(S)-2-HPP epoxidase, (S)-2-hydroxypropylphosphonate epoxidase, (S)-2-hydroxypropylphosphonic acid epoxidase, (S-HPP) epoxidase, 2-hydroxypropylphosphonic acid epoxidase, EC 1.14.19.7, fom4, fosfomycin-producing epoxidase, HPP epoxidase, HppE, Ps-HppE
ECTree
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Reaction
Reaction on EC 1.11.1.23 - (S)-2-hydroxypropylphosphonic acid epoxidase
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(S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O
a straightforward epoxidase mechanism is proposed that depends on the Lewis acid properties of divalent cations and the redox properties of FMN
(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
(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
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(S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O
Tyr105 is a key residue, which plays a role in the activation of dioxygen required for the enzymatic activity of HppE