KEGG   ORTHOLOGY: K12904
Entry
K12904            Tight     KO                                     
Symbol
phpC
Name
phosphonoacetaldehyde reductase [EC:1.1.1.309]
Pathway
map00440  Phosphonate and phosphinate metabolism
map00998  Biosynthesis of various antibiotics
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Reaction
R09478  2-hydroxyethylphosphonate:NAD+ oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00440 Phosphonate and phosphinate metabolism
    K12904  phpC; phosphonoacetaldehyde reductase
  09110 Biosynthesis of other secondary metabolites
   00998 Biosynthesis of various antibiotics
    K12904  phpC; phosphonoacetaldehyde reductase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.309  phosphonoacetaldehyde reductase (NADH)
     K12904  phpC; phosphonoacetaldehyde reductase
Genes
AG: AAU00078(phpC)
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: 1.1.1.309
Entry
EC 1.1.1.309                Enzyme                                 
Name
phosphonoacetaldehyde reductase (NADH);
PhpC
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
2-hydroxyethylphosphonate:NAD+ oxidoreductase
Reaction(IUBMB)
2-hydroxyethylphosphonate + NAD+ = phosphonoacetaldehyde + NADH + H+ [RN:R09478]
Reaction(KEGG)
R09478
Substrate
2-hydroxyethylphosphonate [CPD:C06451];
NAD+ [CPD:C00003]
Product
phosphonoacetaldehyde [CPD:C03167];
NADH [CPD:C00004];
H+ [CPD:C00080]
Comment
The enzyme from Streptomyces viridochromogenes catalyses a step in the biosynthesis of phosphinothricin tripeptide, the reduction of phosphonoacetaldehyde to 2-hydroxyethylphosphonate. The preferred cofactor is NADH, lower activity with NADPH [1].
History
EC 1.1.1.309 created 2011
Pathway
ec00440  Phosphonate and phosphinate metabolism
ec00998  Biosynthesis of various antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12904  phosphonoacetaldehyde reductase
Reference
1  [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:AAU00078]
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.309
IUBMB Enzyme Nomenclature: 1.1.1.309
ExPASy - ENZYME nomenclature database: 1.1.1.309
BRENDA, the Enzyme Database: 1.1.1.309
LinkDB

KEGG   REACTION: R09478
Entry
R09478                      Reaction                               
Name
2-hydroxyethylphosphonate:NAD+ oxidoreductase
Definition
2-Hydroxyethylphosphonate + NAD+ <=> Phosphonoacetaldehyde + NADH + H+
Equation
C06451 + C00003 <=> C03167 + C00004 + C00080
Reaction class
RC00001  C00003_C00004
RC00087  C03167_C06451
Enzyme
1.1.1.309
Pathway
rn00440  Phosphonate and phosphinate metabolism
rn00998  Biosynthesis of various antibiotics
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.309
     R09478  2-Hydroxyethylphosphonate + NAD+ <=> Phosphonoacetaldehyde + NADH + H+
Orthology
K12904  phosphonoacetaldehyde reductase [EC:1.1.1.309]
Other DBs
RHEA: 28081
LinkDB

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