EC 1.11.1.23 - (S)-2-hydroxypropylphosphonic acid epoxidase

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IntEnz Enzyme Nomenclature
EC 1.11.1.23

Names

Accepted name:
(S)-2-hydroxypropylphosphonic acid epoxidase
Other names:
HPP epoxidase
HppE
2-hydroxypropylphosphonic acid epoxidase
Fom4
(S)-2-hydroxypropylphosphonate epoxidase
Systematic name:
(S)-2-hydroxypropylphosphonate:hydrogen-peroxide epoxidase

Reaction

Cofactor

Comments:

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].

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
UniProtKB/Swiss-Prot:

References

  1. Munos, J. W., Moon, S. J., Mansoorabadi, S. O., Chang, W., Hong, L., Yan, F., Liu, A., Liu, H. W.
    Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae.
    Biochemistry 47: 8726-8735 (2008). [PMID: 18656958]
  2. 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.
    Biochemistry 46: 12628-12638 (2007). [PMID: 17927218]
  3. 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: 274-280 (1995). [PMID: 7500951]
  4. Liu, P., Mehn, M. P., Yan, F., Zhao, Z., Que, L., Liu, H. W.
    Oxygenase activity in the self-hydroxylation of (S)-2-hydroxypropylphosphonic acid epoxidase involved in fosfomycin biosynthesis.
    J. Am. Chem. Soc. 126: 10306-10312 (2004). [PMID: 15315444]
  5. Higgins, L. J., Yan, F., Liu, P., Liu, H. W., Drennan, C. L.
    Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron enzyme.
    Nature 437: 838-844 (2005). [PMID: 16015285]
  6. Cameron, S., McLuskey, K., Chamberlayne, R., Hallyburton, I., Hunter, W. N.
    Initiating a crystallographic analysis of recombinant (S)-2-hydroxypropylphosphonic acid epoxidase from Streptomyces wedmorensis.
    Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 61: 534-536 (2005). [PMID: 16511089]
  7. Wang, C., Chang, W. C., Guo, Y., Huang, H., Peck, S. C., Pandelia, M. E., Lin, G. M., Liu, H. W., Krebs, C., Bollinger, J. M.
    Evidence that the fosfomycin-producing epoxidase, HppE, is a non-heme-iron peroxidase.
    Science 342: 991-995 (2013). [PMID: 24114783]

[EC 1.11.1.23 created 2011 as EC 1.14.19.7, 2014 transferred to EC 1.11.1.23]