KEGG   ORTHOLOGY: K12905
Entry
K12905            Tight     KO                                     
Symbol
phpD
Name
2-hydroxyethylphosphonate dioxygenase [EC:1.13.11.72]
Pathway
map00440  Phosphonate and phosphinate metabolism
map01110  Biosynthesis of secondary metabolites
Reaction
R08864  2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00440 Phosphonate and phosphinate metabolism
    K12905  phpD; 2-hydroxyethylphosphonate dioxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.13  Acting on single donors with incorporation of molecular oxygen (oxygenases)
   1.13.11  With incorporation of two atoms of oxygen
    1.13.11.72  2-hydroxyethylphosphonate dioxygenase
     K12905  phpD; 2-hydroxyethylphosphonate dioxygenase
Genes
AG: AAU00079(phpD)
Reference
PMID:17632514
  Authors
Blodgett JA, Thomas PM, Li G, Velasquez JE, van der Donk WA, Kelleher NL, Metcalf WW
  Title
Unusual transformations in the biosynthesis of the antibiotic phosphinothricin tripeptide.
  Journal
Nat Chem Biol 3:480-5 (2007)
DOI:10.1038/nchembio.2007.9
  Sequence
[ag:AAU00079]
Reference
PMID:19489722
  Authors
Metcalf WW, van der Donk WA
  Title
Biosynthesis of phosphonic and phosphinic acid natural products.
  Journal
Annu Rev Biochem 78:65-94 (2009)
DOI:10.1146/annurev.biochem.78.091707.100215
LinkDB

KEGG   ENZYME: 1.13.11.72
Entry
EC 1.13.11.72               Enzyme                                 
Name
2-hydroxyethylphosphonate dioxygenase;
HEPD;
phpD (gene name);
2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)
Class
Oxidoreductases;
Acting on single donors with incorporation of molecular oxygen (oxygenases);
With incorporation of two atoms of oxygen
Sysname
2-hydroxyethylphosphonate:oxygen 1,2-oxidoreductase (hydroxymethylphosphonate-forming)
Reaction(IUBMB)
2-hydroxyethylphosphonate + O2 = hydroxymethylphosphonate + formate [RN:R08864]
Reaction(KEGG)
R08864
Substrate
2-hydroxyethylphosphonate [CPD:C06451];
O2 [CPD:C00007]
Product
hydroxymethylphosphonate [CPD:C06455];
formate [CPD:C00058]
Comment
Requires non-heme-iron(II). Isolated from some bacteria including Streptomyces hygroscopicus and Streptomyces viridochromogenes. The pro-R hydrogen at C-2 of the ethyl group is retained by the formate ion. Any stereochemistry at C-1 of the ethyl group is lost. One atom from dioxygen is present in each product. Involved in phosphinothricin biosynthesis.
History
EC 1.13.11.72 created 2012
Pathway
ec00440  Phosphonate and phosphinate metabolism
ec01110  Biosynthesis of secondary metabolites
Orthology
K12905  2-hydroxyethylphosphonate dioxygenase
Reference
1  [PMID:19516340]
  Authors
Cicchillo RM, Zhang H, Blodgett JA, Whitteck JT, Li G, Nair SK, van der Donk WA, Metcalf WW
  Title
An unusual carbon-carbon bond cleavage reaction during phosphinothricin biosynthesis.
  Journal
Nature 459:871-4 (2009)
DOI:10.1038/nature07972
  Sequence
[ag:AAU00079]
Reference
2  [PMID:21381767]
  Authors
Whitteck JT, Malova P, Peck SC, Cicchillo RM, Hammerschmidt F, van der Donk WA
  Title
On the stereochemistry of 2-hydroxyethylphosphonate dioxygenase.
  Journal
J Am Chem Soc 133:4236-9 (2011)
DOI:10.1021/ja1113326
Reference
3  [PMID:21711001]
  Authors
Peck SC, Cooke HA, Cicchillo RM, Malova P, Hammerschmidt F, Nair SK, van der Donk WA
  Title
Mechanism and substrate recognition of 2-hydroxyethylphosphonate dioxygenase.
  Journal
Biochemistry 50:6598-605 (2011)
DOI:10.1021/bi200804r
  Sequence
[ag:AAU00079]
Other DBs
ExplorEnz - The Enzyme Database: 1.13.11.72
IUBMB Enzyme Nomenclature: 1.13.11.72
ExPASy - ENZYME nomenclature database: 1.13.11.72
BRENDA, the Enzyme Database: 1.13.11.72
LinkDB

KEGG   REACTION: R08864
Entry
R08864                      Reaction                               
Name
2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)
Definition
2-Hydroxyethylphosphonate + Oxygen <=> Hydroxymethylphosphonate + Formate
Equation
C06451 + C00007 <=> C06455 + C00058
Reaction class
RC03073  C06451_C06455
RC03074  C00058_C06451
Enzyme
1.13.11.72
Pathway
rn00440  Phosphonate and phosphinate metabolism
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.13  Acting on single donors with incorporation of molecular oxygen (oxygenases)
   1.13.11  With incorporation of two atoms of oxygen
    1.13.11.72
     R08864  2-Hydroxyethylphosphonate + Oxygen <=> Hydroxymethylphosphonate + Formate
Orthology
K12905  2-hydroxyethylphosphonate dioxygenase [EC:1.13.11.72]
Other DBs
RHEA: 34794
LinkDB

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