KEGG   ENZYME: 1.11.1.23Help
Entry
EC 1.11.1.23                Enzyme                                 

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
Phosphonate and phosphinate metabolism
Biosynthesis of antibiotics
Orthology
K12903  
(S)-2-hydroxypropylphosphonic acid epoxidase
Reference
1  [PMID:18656958]
  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
Biochemistry. 47 (2008) 8726-35.
  Sequence
Reference
2  [PMID:17927218]
  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
Biochemistry. 46 (2007) 12628-38.
Reference
3  [PMID:7500951]
  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
Mol. Gen. Genet. 249 (1995) 274-80.
  Sequence
Reference
4  [PMID:15315444]
  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
J. Am. Chem. Soc. 126 (2004) 10306-12.
Reference
5  [PMID:16015285]
  Authors
Higgins LJ, Yan F, Liu P, Liu HW, Drennan CL
  Title
Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron  enzyme.
  Journal
Nature. 437 (2005) 838-44.
  Sequence
Reference
6  [PMID:16511089]
  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
Acta. Crystallogr. Sect. F. Struct. Biol. Cryst. Commun. 61 (2005) 534-6.
Reference
7  [PMID:24114783]
  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
Science. 342 (2013) 991-5.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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