1.11.1.23: (S)-2-hydroxypropylphosphonic acid epoxidase

This is an abbreviated version!
For detailed information about (S)-2-hydroxypropylphosphonic acid epoxidase, go to the full flat file.

Word Map on EC 1.11.1.23

Reaction

(S)-2-hydroxypropylphosphonate
+
H2O2
=
(1R,2S)-1,2-epoxypropylphosphonate
+ 2 H2O

Synonyms

(S)-2-HPP epoxidase, (S)-2-hydroxypropylphosphonic acid epoxidase, (S-HPP) epoxidase, 2-hydroxypropylphosphonic acid epoxidase, fom4, fosfomycin-producing epoxidase, HPP epoxidase, HppE, Ps-HppE

ECTree

     1 Oxidoreductases
         1.11 Acting on a peroxide as acceptor
             1.11.1 Peroxidases
                1.11.1.23 (S)-2-hydroxypropylphosphonic acid epoxidase

Reference

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

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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
61
534-536
2005
Streptomyces wedmorensis (Q56185), Streptomyces wedmorensis
Manually annotated by BRENDA team
Zhao, Z.; Liu, P.; Murakami, K.; Kuzuyama, T.; Seto, H.; Liu, H.W.
Mechanistic studies of HPP epoxidase: configuration of the substrate governs its enzymatic fate
Angew. Chem. Int. Ed. Engl.
41
4529-4532
2002
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Watanabe, M.; Sumida, N.; Murakami, S.; Anzai, H.; Thompson, C.J.; Tateno, Y.; Murakami, T.
A phosphonate-induced gene which promotes Penicillium-mediated bioconversion of cis-propenylphosphonic acid to fosfomycin
Appl. Environ. Microbiol.
65
1036-1044
1999
Penicillium decumbens
Manually annotated by BRENDA team
Yan, F.; Li, T.; Lipscomb, J.D.; Liu, A.; Liu, H.W.
Site-directed mutagenesis and spectroscopic studies of the iron-binding site of (S)-2-hydroxypropylphosphonic acid epoxidase
Arch. Biochem. Biophys.
442
82-91
2005
Streptomyces wedmorensis (Q56185), Streptomyces wedmorensis
Manually annotated by BRENDA team
Liu, P.; Liu, A.; Yan, F.; Wolfe, M.D.; Lipscomb, J.D.; Liu, H.W.
Biochemical and spectroscopic studies on (S)-2-hydroxypropylphosphonic acid epoxidase: a novel mononuclear non-heme iron enzyme
Biochemistry
42
11577-11586
2003
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Yan, F.; Munos, J.W.; Liu, P.; Liu, H.W.
Biosynthesis of fosfomycin, re-examination and re-confirmation of a unique Fe(II)- and NAD(P)H-dependent epoxidation reaction
Biochemistry
45
11473-11481
2006
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
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
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
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
Pseudomonas syringae
Manually annotated by BRENDA team
Schweifer, A.; Hammerschmidt, F.
On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae
Bioorg. Med. Chem. Lett.
18
3056-3059
2008
Streptomyces fradiae (D2SNF6)
Manually annotated by BRENDA team
Kuzuyama, T.; Seki, T.; Kobayashi, S.; Hidaka, T.; Seto, H.
Cloning and expression in Escherichia coli of 2-hydroxypropylphosphonic acid epoxidase from the fosfomycin-producing organism, Pseudomonas syringae PB-5123
Biosci. Biotechnol. Biochem.
63
2222-2224
1999
Pseudomonas syringae (Q9JN69), Pseudomonas syringae PB-5123, Pseudomonas syringae PB-5123 (Q9JN69)
Manually annotated by BRENDA team
Liu, P.; Murakami, K.; Seki, T.; He, X.; Yeung, S.M.; Kuzuyama, T.; Seto, H.; Liu, H.
Protein purification and function assignment of the epoxidase catalyzing the formation of fosfomycin
J. Am. Chem. Soc.
123
4619-4620
2001
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Liu, P.; Mehn, M.P.; Yan, F.; Zhao, Z.; Que, L. Jr.; 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
Streptomyces wedmorensis (Q56185), Streptomyces wedmorensis
Manually annotated by BRENDA team
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
Streptomyces wedmorensis 144-91 (Q56185), Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
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
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
McLuskey, K.; Cameron, S.; Hammerschmidt, F.; Hunter, W.N.
Structure and reactivity of hydroxypropylphosphonic acid epoxidase in fosfomycin biosynthesis by a cation- and flavin-dependent mechanism
Proc. Natl. Acad. Sci. USA
102
14221-14226
2005
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Milaczewska, A.; Broclawik, E.; Borowski, T.
On the catalytic mechanism of (S)-2-hydroxypropylphosphonic acid epoxidase (HppE): a hybrid DFT study
Chemistry
19
771-781
2013
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Huang, H.; Chang, W.C.; Pai, P.J.; Romo, A.; Mansoorabadi, S.O.; Russell, D.H.; Liu, H.W.
Evidence for radical-mediated catalysis by HppE: a study using cyclopropyl and methylenecyclopropyl substrate analogues
J. Am. Chem. Soc.
134
16171-16174
2012
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Chang, W.C.; Mansoorabadi, S.O.; Liu, H.W.
Reaction of HppE with substrate analogues: evidence for carbon-phosphorus bond cleavage by a carbocation rearrangement
J. Am. Chem. Soc.
135
8153-8156
2013
Streptomyces wedmorensis (Q56185)
Manually annotated by BRENDA team
Huang, H.; Chang, W.C.; Lin, G.M.; Romo, A.; Pai, P.J.; Russell, W.K.; Russell, D.H.; Liu, H.W.
Mechanistic consequences of chiral radical clock probes: analysis of the mononuclear non-heme iron enzyme HppE with 2-hydroxy-3-methylenecyclopropyl radical clock substrates
J. Am. Chem. Soc.
136
2944-2947
2014
Streptomyces wedmorensis
Manually annotated by BRENDA team
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
Yersinia pseudotuberculosis
Manually annotated by BRENDA team