(S)-2-hydroxypropylphosphonic acid epoxidase

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(S)-2-hydroxypropylphosphonic acid epoxidase
EC number
IntEnz IntEnz view
ExPASy NiceZyme view
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum

(S)-2-hydroxypropylphosphonic acid epoxidase (EC, HPP epoxidase, HppE, 2-hydroxypropylphosphonic acid epoxidase, Fom4, (S)-2-hydroxypropylphosphonate epoxidase) is an enzyme with systematic name (S)-2-hydroxypropylphosphonate,NADH:oxygen epoxidase.[1][2][3][4][5][6] This enzyme catalyses the following chemical reaction

(S)-2-hydroxypropylphosphonate + NADH + H+ + O2 (1R,2S)-epoxypropylphosphonate + NAD+ + 2 H2O

(S)-2-hydroxypropylphosphonic acid epoxidase contains one non-heme iron centre per monomer.


  1. ^ Munos, J.W.; Moon, S.J.; Mansoorabadi, S.O.; Chang, W.; Hong, L.; Yan, F.; Liu, A.; Liu, H.W. (2008). "Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae". Biochemistry. 47 (33): 8726–8735. doi:10.1021/bi800877v. PMC 2780581Freely accessible. PMID 18656958. 
  2. ^ Yan, F.; Moon, S.J.; Liu, P.; Zhao, Z.; Lipscomb, J.D.; Liu, A.; Liu, H.W. (2007). "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 (44): 12628–12638. doi:10.1021/bi701370e. PMC 2780580Freely accessible. PMID 17927218. 
  3. ^ Hidaka, T.; Goda, M.; Kuzuyama, T.; Takei, N.; Hidaka, M.; Seto, H. (1995). "Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis". Mol. Gen. Genet. 249 (3): 274–280. doi:10.1007/bf00290527. PMID 7500951. 
  4. ^ Liu, P.; Mehn, M.P.; Yan, F.; Zhao, Z.; Que, L.; Jr.; Liu, H.W. (2004). "Oxygenase activity in the self-hydroxylation of (S)-2-hydroxypropylphosphonic acid epoxidase involved in fosfomycin biosynthesis". J. Am. Chem. Soc. 126 (33): 10306–10312. doi:10.1021/ja0475050. PMID 15315444. 
  5. ^ Higgins, L.J.; Yan, F.; Liu, P.; Liu, H.W.; Drennan, C.L. (2005). "Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron enzyme". Nature. 437 (7060): 838–844. doi:10.1038/nature03924. PMID 16015285. 
  6. ^ Cameron, S.; McLuskey, K.; Chamberlayne, R.; Hallyburton, I.; Hunter, W.N. (2005). "Initiating a crystallographic analysis of recombinant (S)-2-hydroxypropylphosphonic acid epoxidase from Streptomyces wedmorensis". Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 61 (Pt 5): 534–536. doi:10.1107/S1744309105012376. PMC 1952317Freely accessible. PMID 16511089. 

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