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
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