KEGG   ENZYME: 1.13.11.72Help
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
BRITE hierarchy
Sysname
2-hydroxyethylphosphonate:oxygen 1,2-oxidoreductase (hydroxymethylphosphonate forming)
Reaction(IUBMB)
2-hydroxyethylphosphonate + O2 = hydroxymethylphosphonate + formate [RN:R08864]
Reaction(KEGG)
Substrate
2-hydroxyethylphosphonate [CPD:C06451];
O2 [CPD:C00007]
Product
hydroxymethylphosphonate [CPD:C06455];
formate [CPD:C00058]
Comment
Requires non-heme-Fe(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
Phosphonate and phosphinate metabolism
Biosynthesis of antibiotics
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 (2009) 871-4.
  Sequence
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 (2011) 4236-9.
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 (2011) 6598-605.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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