1.11.1.23: (S)-2-hydroxypropylphosphonic acid epoxidase
This is an abbreviated version!
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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Substrates Products
Substrates Products on EC 1.11.1.23 - (S)-2-hydroxypropylphosphonic acid epoxidase
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REACTION DIAGRAM
(3,3,3-trifluoro-1-hydroxypropyl)phosphonic acid + H2O2
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(R)-2-hydroxypropylphosphonate + H2O2
2-oxo-propylphosphonic acid + H2O
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(R)-2-hydroxypropylphosphonate + H2O2
2-oxopropylphosphonic acid + H2O
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(R)-2-hydroxypropylphosphonate + NADH + H+ + O2
2-oxopropylphosphonic acid + NAD+ + H2O
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(R)-2-hydroxypropylphosphonic acid + H2O2
2-oxo-propylphosphonic acid + H2O
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(S)-2-hydroxybutylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxybutylphosphonic acid + 2 H2O + 2 NAD+
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(S)-2-hydroxypropyl-1-phosphonate + H2O2
(1R,2S)-1,2-epoxypropylphosphonate + H2O
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i.e. fosfomycin
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(S)-2-hydroxypropylphosphonate + H2O2
cis-fosfomycin + trans-fosfomycin + 2 H2O
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(S)-2-hydroxypropylphosphonate + NADH + H+ + O2
(1R,2S)-epoxypropylphosphonate + NAD+ + H2O
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i.e. fosfomycin
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(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
[(1R)-3,3,3-trifluoro-1-hydroxypropyl]phosphonate + H2O2
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[(2R)-2-hydroxy-2-[(1R)-2-methylidenecyclopropyl]ethyl]phosphonate + H2O2
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[(2R)-2-hydroxy-2-[(1S)-2-methylidenecyclopropyl]ethyl]phosphonate + H2O2
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[(2R,3S)-3-[(1R)-2-methylidenecyclopropyl]oxiran-2-yl]phosphonate + H2O2
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[(2R,3S)-3-[(1S)-2-methylidenecyclopropyl]oxiran-2-yl]phosphonate + H2O2
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[(2S)-2-hydroxy-2-(2-methylidenecyclopropyl)ethyl]phosphonate + H2O2
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[(2S)-2-hydroxy-2-[(1R)-2-methylidenecyclopropyl]ethyl]phosphonic acid + H2O2
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[2-[(1S)-2-methylidenecyclopropyl]-2-oxoethyl]phosphonate + H2O2
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[3-(2-methylidenecyclopropyl)oxiran-2-yl]phosphonate + H2O2
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(1R,2S)-1,2-epoxypropylphosphonate + H2O
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(S)-2-hydroxypropylphosphonate + H2O2
(1R,2S)-1,2-epoxypropylphosphonate + H2O
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cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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i.e. fosfomycin
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(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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if either iron, FMN, or NADH is omitted from the reaction mixture, no product formation is detected
i.e. fosfomycin
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(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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i.e. fosfomycin
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?
(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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i.e. fosfomycin
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?
(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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-
i.e. fosfomycin
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?
(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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i.e. fosfomycin
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?
(S)-2-hydroxypropylphosphonic acid + 2 NADH + O2
cis-(1R,2S)-epoxypropylphosphonic acid + 2 H2O + 2 NAD+
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
i.e. fosfomycin
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[(2R)-2-cyclopropyl-2-hydroxyethyl]phosphonate + H2O2
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[(2S)-2-cyclopropyl-2-hydroxyethyl]phosphonate + H2O2
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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
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additional information
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no activity with 2-hydroxyethyl phosphonic acid
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additional information
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the enzyme also forms 2-oxopropylphosphonic acid from (R)-2-hydroxypropylphosphonic acid. HPP epoxidase is not selective with regard to substrate recognition, but can stereospecifically convert each enantiomer into a unique product with similar efficiency
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