(S)-2-hydroxypropylphosphonic acid epoxidase;
HPP epoxidase;
HppE;
2-hydroxypropylphosphonic acid epoxidase;
Fom4;
(S)-2-hydroxypropylphosphonate epoxidase

Oxidoreductases;
Acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water

(S)-2-hydroxypropylphosphonate,NADH:oxygen epoxidase

(S)-2-hydroxypropylphosphonate + NADH + H+ + O2 = (1R,2S)-epoxypropylphosphonate + NAD+ + 2 H2O [RN:R08863]

R08863

(S)-2-hydroxypropylphosphonate [CPD:C06452];
NADH [CPD:C00004];
H+ [CPD:C00080];
O2 [CPD:C00007]

Contains one non-heme iron centre per monomer [1,5]. FMN is required to mediate the transfer of reducing equivalents from NADH to the active site iron [1]. This is the last enzyme in the biosynthetic pathway of fosfomycin, a broad-spectrum antibiotic produced by certain Streptomyces species.

1  [PMID:18656958]

Munos JW, Moon SJ, Mansoorabadi SO, Chang W, Hong L, Yan F, Liu A, Liu HW

Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae.

Biochemistry. 47 (2008) 8726-35.

Streptomyces wedmorensis, Pseudomonas syringae

2  [PMID:17927218]

Yan F, Moon SJ, Liu P, Zhao Z, Lipscomb JD, Liu A, Liu HW

Determination of the substrate binding mode to the active site iron of (S)-2-hydroxypropylphosphonic acid epoxidase using 17O-enriched substrates and substrate analogues.

Biochemistry. 46 (2007) 12628-38.

Streptomyces wedmorensis

3  [PMID:7500951]

Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H

Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces  wedmorensis.

Mol. Gen. Genet. 249 (1995) 274-80.

Streptomyces wedmorensis

4  [PMID:15315444]

Liu P, Mehn MP, Yan F, Zhao Z, Que L Jr, Liu HW

Oxygenase activity in the self-hydroxylation of (s)-2-hydroxypropylphosphonic acid epoxidase involved in fosfomycin biosynthesis.

J. Am. Chem. Soc. 126 (2004) 10306-12.

Streptomyces wedmorensis

5  [PMID:16015285]

Higgins LJ, Yan F, Liu P, Liu HW, Drennan CL

Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron  enzyme.

Nature. 437 (2005) 838-44.

Streptomyces wedmorensis

6  [PMID:16511089]

Cameron S, McLuskey K, Chamberlayne R, Hallyburton I, Hunter WN

Initiating a crystallographic analysis of recombinant (S)-2-hydroxypropylphosphonic acid epoxidase from Streptomyces wedmorensis.

Acta. Crystallogr. Sect. F. Struct. Biol. Cryst. Commun. 61 (2005) 534-6.

Streptomyces wedmorensis