Literature summary for 1.11.1.23 extracted from

Yan, F.; Moon, S.J.; Liu, P.; Zhao, Z.; Lipscomb, J.D.; Liu, A.; Liu, H.W.
Determination of the substrate binding mode to the active site iron of (S)-2-hydroxypropylphosphonic acid epoxidase using 17O-enriched substrates and substrate analogues (2007), Biochemistry, 46, 12628-12638.

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Metals/Ions

Metals/Ions	Comment	Organism	Structure
Iron	O2 binds to the iron, and substrates bind in a single orientation that strongly perturbs the iron environment. Both functional groups of (S)-2-hydroxypropylphosphonic acid bind to Fe(II) ion at the same time as NO, suggesting that the chelated substrate binding mode dominates in solution. The Fe(II)-substrate chelate structure is important to active fosfomycin formation. This fixed orientation may align the substrate next to the iron-bound activated oxygen species thought to mediate hydrogen atom abstraction from the nearest substrate carbon	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	-	-

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

Synonyms

Synonyms	Comment	Organism
fom4	-	Streptomyces wedmorensis
HppE	-	Streptomyces wedmorensis

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Release 2023.1 (January 2023)