| Entry |
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| Name |
(S)-2-hydroxypropylphosphonic acid epoxidase;
HPP epoxidase;
HppE;
2-hydroxypropylphosphonic acid epoxidase;
Fom4;
(S)-2-hydroxypropylphosphonate epoxidase
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| Class |
Oxidoreductases;
Acting on a peroxide as acceptor;
Peroxidases
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| Sysname |
(S)-2-hydroxypropylphosphonate:hydrogen-peroxide epoxidase
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| Reaction(IUBMB) |
(S)-2-hydroxypropylphosphonate + H2O2 = (1R,2S)-1,2-epoxypropylphosphonate + 2 H2O [RN: R08863]
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| Reaction(KEGG) |
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| Substrate |
(S)-2-hydroxypropylphosphonate [CPD: C06452];
H2O2 [CPD: C00027]
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| Product |
(1R,2S)-1,2-epoxypropylphosphonate;
H2O [CPD: C00001]
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| 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].
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| History |
EC 1.11.1.23 created 2011 as EC 1.14.19.7, transferred 2014 to EC 1.11.1.23
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| Pathway |
| Phosphonate and phosphinate metabolism | | Biosynthesis of antibiotics |
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| Orthology |
| (S)-2-hydroxypropylphosphonic acid epoxidase |
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| Reference |
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| Authors |
Munos JW, Moon SJ, Mansoorabadi SO, Chang W, Hong L, Yan F, Liu A, Liu HW |
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| Title |
Purification and characterization of the epoxidase catalyzing the formation of fosfomycin from Pseudomonas syringae. |
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| Journal |
Biochemistry. 47 (2008) 8726-35. |
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| Sequence |
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| Reference |
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| Authors |
Yan F, Moon SJ, Liu P, Zhao Z, Lipscomb JD, Liu A, Liu HW |
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| 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. |
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| Journal |
Biochemistry. 46 (2007) 12628-38. |
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| Reference |
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| Authors |
Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H |
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| Title |
Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis. |
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| Journal |
Mol. Gen. Genet. 249 (1995) 274-80. |
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| Sequence |
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| Reference |
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| Authors |
Liu P, Mehn MP, Yan F, Zhao Z, Que L Jr, Liu HW |
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| Title |
Oxygenase activity in the self-hydroxylation of (s)-2-hydroxypropylphosphonic acid epoxidase involved in fosfomycin biosynthesis. |
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| Journal |
J. Am. Chem. Soc. 126 (2004) 10306-12. |
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| Reference |
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| Authors |
Higgins LJ, Yan F, Liu P, Liu HW, Drennan CL |
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| Title |
Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron enzyme. |
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| Journal |
Nature. 437 (2005) 838-44. |
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| Sequence |
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| Reference |
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| Authors |
Cameron S, McLuskey K, Chamberlayne R, Hallyburton I, Hunter WN |
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| Title |
Initiating a crystallographic analysis of recombinant (S)-2-hydroxypropylphosphonic acid epoxidase from Streptomyces wedmorensis. |
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| Journal |
Acta. Crystallogr. Sect. F. Struct. Biol. Cryst. Commun. 61 (2005) 534-6. |
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| Reference |
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| Authors |
Wang C, Chang WC, Guo Y, Huang H, Peck SC, Pandelia ME, Lin GM, Liu HW, Krebs C, Bollinger JM Jr |
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| Title |
Evidence that the fosfomycin-producing epoxidase, HppE, is a non-heme-iron peroxidase. |
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| Journal |
Science. 342 (2013) 991-5. |
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| Other DBs |
ExplorEnz - The Enzyme Database: IUBMB Enzyme Nomenclature: ExPASy - ENZYME nomenclature database: BRENDA, the Enzyme Database: |
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| LinkDB |
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