Entry
Name
(S)-2-hydroxypropylphosphonic acid epoxidase;
HPP epoxidase;
HppE;
2-hydroxypropylphosphonic acid epoxidase;
Fom4;
(S)-2-hydroxypropylphosphonate epoxidase
Class
Oxidoreductases;
Acting on a peroxide as acceptor;
Peroxidases
BRITE hierarchy
Sysname
(S)-2-hydroxypropylphosphonate:hydrogen-peroxide epoxidase
Reaction(IUBMB)
(S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O [RN:
R08863 ]
Reaction(KEGG)
Substrate
(S)-2-hydroxypropylphosphonate [CPD:
C06452 ];
H2O2 [CPD:
C00027 ]
Product
(1R,2S)-1,2-epoxypropylphosphonate;
H2O [CPD:
C00001 ]
Comment
This is the last enzyme in the biosynthetic pathway of fosfomycin, a broad-spectrum antibiotic produced by certain Streptomyces species. Contains non heme iron that forms a iron(IV)-oxo (ferryl) complex with hydrogen peroxide, which functions as a proton abstractor from the substrate [7].
History
EC 1.11.1.23 created 2011 as EC 1.14.19.7, transferred 2014 to EC 1.11.1.23
Pathway
ec00998 Biosynthesis of various antibiotics
ec01110 Biosynthesis of secondary metabolites
Orthology
K12903 (S)-2-hydroxypropylphosphonic acid epoxidase
K22392 (S)-2-hydroxypropylphosphonic acid epoxidase
Reference
Authors
Munos JW, Moon SJ, Mansoorabadi SO, Chang W, Hong L, Yan F, Liu A, Liu HW
Title
Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae.
Journal
Sequence
Reference
Authors
Yan F, Moon SJ, Liu P, Zhao Z, Lipscomb JD, Liu A, Liu HW
Title
Determination of the substrate binding mode to the active site iron of (S)-2-hydroxypropylphosphonic acid epoxidase using 17O-enriched substrates and substrate analogues.
Journal
Reference
Authors
Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H
Title
Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis.
Journal
Sequence
Reference
Authors
Liu P, Mehn MP, Yan F, Zhao Z, Que L Jr, Liu HW
Title
Oxygenase activity in the self-hydroxylation of (s)-2-hydroxypropylphosphonic acid epoxidase involved in fosfomycin biosynthesis.
Journal
Reference
Authors
Higgins LJ, Yan F, Liu P, Liu HW, Drennan CL
Title
Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron enzyme.
Journal
Sequence
Reference
Authors
Cameron S, McLuskey K, Chamberlayne R, Hallyburton I, Hunter WN
Title
Initiating a crystallographic analysis of recombinant (S)-2-hydroxypropylphosphonic acid epoxidase from Streptomyces wedmorensis.
Journal
Reference
Authors
Wang C, Chang WC, Guo Y, Huang H, Peck SC, Pandelia ME, Lin GM, Liu HW, Krebs C, Bollinger JM Jr
Title
Evidence that the fosfomycin-producing epoxidase, HppE, is a non-heme-iron peroxidase.
Journal
Other DBs
ExPASy - ENZYME nomenclature database: 1.11.1.23