KEGG   PATHWAY: dao00440Help
Entry
dao00440                    Pathway                                

Name
Phosphonate and phosphinate metabolism - Desulfobacca acetoxidans
Description
Natural products containing carbon-phosphorous bonds, so-called C-P compounds, are derivatives of phosphonate and phosphinate with substitution of alkyl group for hydrogen of phosphorus-hydrogen bonds. C-P compounds have been found in many organisms, but only protists and bacteria, mostly Actinobacteria, have biosynthetic capacity. A common reaction in the biosynthetic pathway is C-P bond forming reaction from phosphoenolpyruvate (PEP) to phosphonopyruvate (PnPy) catalyzed by PEP phosphomutase. 2-Aminoethylphosphonate (AEP) is the most abundant C-P compound in the natural world. AEP derivatives include phosphonoprotein, phosphonoglycan, and phosphonolipid. Other known C-P compounds are bioactive substances used in medicine (antibiotics) and agriculture (herbicide) such as fosfomycin, FR-33289, rhizocticin, and bialaphos.
Class
Metabolism; Metabolism of other amino acids
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Pathway map
dao00440  Phosphonate and phosphinate metabolism
dao00440

Ortholog table
Other DBs
BSID: 215972
GO: 0019634
Organism
Desulfobacca acetoxidans [GN:dao]
Gene
Desac_2268  phosphoenolpyruvate phosphomutase [KO:K01841] [EC:5.4.2.9]
Desac_2269  phosphonopyruvate decarboxylase [KO:K09459] [EC:4.1.1.82]
Desac_2271  2-aminoethylphosphonate aminotransferase [KO:K03430] [EC:2.6.1.37]
Compound
C00022  Pyruvate
C00033  Acetate
C00037  Glycine
C00074  Phosphoenolpyruvate
C00084  Acetaldehyde
C00117  D-Ribose 5-phosphate
C01151  D-Ribose 1,5-bisphosphate
C01438  Methane
C02798  3-Phosphonopyruvate
C03167  Phosphonoacetaldehyde
C03557  2-Aminoethylphosphonate
C04650  L-Phosphinothricin
C05672  2-Amino-3-phosphonopropanoate
C05673  CMP-2-aminoethylphosphonate
C05674  CMP-N-trimethyl-2-aminoethylphosphonate
C05675  Diacylglyceryl-2-aminoethylphosphonate
C05676  Diacylglyceryl-N-trimethyl-2-aminoethylphosphonate
C05677  Lipophosphonoglycan
C05678  (2-Amino-1-hydroxyethyl)phosphonate
C05679  N-Monomethyl-2-aminoethylphosphonate
C05680  N-Dimethyl-2-aminoethylphosphonate
C05681  Ceramide 2-aminoethylphosphonate
C05682  Phosphonoacetate
C05683  Ciliatocholate
C06367  1-Carboxyvinyl carboxyphosphonate
C06368  3-(Hydrohydroxyphosphoryl)pyruvate
C06451  2-Hydroxyethylphosphonate
C06452  (S)-2-Hydroxypropylphosphonate
C06454  Fosfomycin
C06455  Hydroxymethylphosphonate
C06456  Phosphonoformate
C06457  Bialaphos
C06459  N-Trimethyl-2-aminoethylphosphonate
C17940  Rhizocticin B
C17941  2-Oxo-4-phosphonobutanoate
C17942  FR 900098
C17943  Formylphosphonate
C17944  Rhizocticin A
C17945  Phosphonoformyl-CMP
C17947  2-Phosphinomethylmalate
C17948  Deamino-alpha-keto-demethylphosphinothricin
C17949  N-Acetyldemethylphosphinothricin
C17950  N-Acetyldemethylphosphinothricin tripeptide
C17951  N-Acetylbialaphos
C17952  N-Acetylphosphinothricin
C17960  Rhizocticin C
C17961  Rhizocticin D
C17962  Demethylphosphinothricin
C20396  Methylphosphonate
C20422  alpha-D-Ribose 1-methylphosphonate 5-triphosphate
C20423  alpha-D-Ribose 1-methylphosphonate 5-phosphate
C20440  alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate
C20986  D-Ribose 2,5-bisphosphate
C21372  3-Phosphinomethylmalate
C21403  2-Acetamidoethylphosphonate
C21404  N-Ethylacetamide
C21613  (R)-2-(Phosphonomethyl)malate
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
Reference
  Authors
Xiao Y, Lee K, Liu P
  Title
Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.
  Journal
Org Lett 10:5521-4 (2008)
DOI:10.1021/ol802269x
Reference
  Authors
van der Donk WA
  Title
Rings, radicals, and regeneration: the early years of a bioorganic laboratory.
  Journal
J Org Chem 71:9561-71 (2006)
DOI:10.1021/jo0614240
Reference
  Authors
Blodgett JA, Zhang JK, Metcalf WW
  Title
Molecular cloning, sequence analysis, and heterologous expression of the phosphinothricin tripeptide biosynthetic gene cluster from Streptomyces viridochromogenes DSM 40736.
  Journal
Antimicrob Agents Chemother 49:230-40 (2005)
DOI:10.1128/AAC.49.1.230-240.2005
Reference
  Authors
Schwartz D, Berger S, Heinzelmann E, Muschko K, Welzel K, Wohlleben W
  Title
Biosynthetic gene cluster of the herbicide phosphinothricin tripeptide from Streptomyces viridochromogenes Tu494.
  Journal
Appl Environ Microbiol 70:7093-102 (2004)
DOI:10.1128/AEM.70.12.7093-7102.2004
KO pathway
ko00440   
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