KEGG   ORTHOLOGY: K12905Help
Entry
K12905                      KO                                     

Name
phpD
Definition
2-hydroxyethylphosphonate dioxygenase [EC:1.13.11.72]
Pathway
ko00440  Phosphonate and phosphinate metabolism
ko01130  Biosynthesis of antibiotics
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
BRITE hierarchy
Other DBs
RN: R08864
Genes
AG: AAU00079(phpD)
TaxonomyKoalaUniProt
Reference
  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
Reference
  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

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
ec00440  Phosphonate and phosphinate metabolism
ec01130  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 459:871-4 (2009)
DOI:10.1038/nature07972
  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 133:4236-9 (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
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

KEGG   REACTION: R08864Help
Entry
R08864                      Reaction                               

Name
2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)
Definition
2-Hydroxyethylphosphonate + Oxygen <=> Hydroxymethylphosphonate + Formate
Equation
Reaction class
RC03073  C06451_C06455
RC03074  C00058_C06451
Enzyme
Pathway
rn00440  Phosphonate and phosphinate metabolism
rn01130  Biosynthesis of antibiotics
Orthology
K12905  2-hydroxyethylphosphonate dioxygenase [EC:1.13.11.72]
Other DBs
RHEA: 34794

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